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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (111)transporters (1) Show 112 proteins XML

enzymes (111)transporters (1) Show 112 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001113

Secondary Accession Numbers

HMDB01113

Metabolite Identification

Common Name

Isovaleryl-CoA

Description

Isovaleryl-CoA is an intermediate metabolite in the catabolic pathway of leucine. The accumulation of derivatives of isovaleryl-CoA occurs in patients affected with isovaleric acidemia (IVA, OMIM: 243500 ), an autosomal recessive inborn error of leucine metabolism caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD, EC 1.3.99.10), a flavoenzyme that catalyzes the conversion of isovaleryl-CoA into 3-methylcrotonyl-CoA. IVA was the first organic acidemia recognized in humans and can cause significant morbidity and mortality. Early diagnosis and treatment with a protein-restricted diet and supplementation with carnitine and glycine are effective in promoting normal development in severely affected individuals. Both intra- and interfamilial variability have been recognized. Initially, two phenotypes with either an acute neonatal or a chronic intermittent presentation were described. More recently, a third group of individuals with mild biochemical abnormalities who can be asymptomatic have been identified through newborn screening of blood spots by tandem mass spectrometry. The majority of patients with IVA today are diagnosed pre-symptomatically through newborn screening by use of MS/MS which reveals elevations of the marker metabolite C5 acylcarnitine in dried blood spots. C5 Acylcarnitine represents a mixture of isomers (isovalerylcarnitine, 2-methylbutyrylcarnitine, and pivaloylcarnitine) (PMID: 16602101 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305132019432D          

 54 56  0  0  1  0            999 V2000
   26.6053   -2.0449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.9379   -1.5600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3504   -2.8295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.2704   -2.0449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.5254   -2.8295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.8353   -3.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8596   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6024   -6.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1451   -6.4984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4307   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7162   -6.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1735   -4.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4307   -5.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1735   -4.0234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7445   -4.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4590   -3.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8880   -2.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7610   -1.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1735   -2.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5859   -1.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4590   -2.7858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7445   -2.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6024   -2.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2524   -2.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9023   -2.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4274   -1.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4274   -3.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0774   -1.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0774   -3.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4274   -2.3733    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.0774   -2.3733    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.4858   -1.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0404   -3.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2154   -4.3220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8654   -4.3220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0404   -4.3220    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.0404   -5.1470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3899   -1.7900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0031   -2.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7255   -1.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7175   -1.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0031   -3.1669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5460   -1.1225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4320   -2.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7176   -3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4320   -3.1669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1464   -1.9294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3169   -6.0859    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.7458   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1747   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0313   -6.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0313   -7.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4603   -6.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4603   -7.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 51  1  0  0  0  0
 51 49  1  0  0  0  0
 49 53  1  0  0  0  0
 53 50  1  0  0  0  0
 51 52  2  0  0  0  0
 53 54  1  0  0  0  0
M  END

HMDB0001113
     RDKit          3D
Isovaleryl-CoA
 98100  0  0  0  0  0  0  0  0999 V2000
   10.8185   -0.3874    1.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3096   -0.9765    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4062   -0.9810   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8207   -2.3725    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3049   -3.1290   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9792   -4.0954   -1.2678 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7401   -2.8058   -1.6571 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9198   -1.4397   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1882   -1.7119    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9538   -0.3760    0.9448 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.0532    1.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3426   -0.8359    2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1896    1.3793    2.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9432    2.1681    2.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    2.3600    1.2856 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    2.5396    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4356    3.2087    0.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    2.0675   -1.2302 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4565    3.0094   -2.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.7358   -1.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871    0.3930   -2.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790   -0.3173   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705    0.8211   -1.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235   -0.3887   -1.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328   -0.2087   -1.3153 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1334   -0.9909   -2.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604    1.3524   -1.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -1.0054    0.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1418    0.0352    1.4016 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.8462    1.4495    1.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453   -0.5421    2.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -0.0844    1.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5238    0.7193    0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0032    0.5371    1.3852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8790    1.2186    0.5917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8611    0.2719    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6320    0.7934   -0.9317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4373    1.8818   -1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3669    2.0670   -2.5471 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2423    1.0028   -2.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3510    0.6834   -3.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9041    1.4521   -4.2108 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0069   -0.5260   -2.8552 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5039   -1.2210   -1.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4343   -0.9399   -1.1608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7351    0.2083   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9384   -0.8693   -0.1851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5362   -2.0174   -0.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2902   -0.9790    1.2131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3112   -1.2181    2.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9898   -1.9718    3.5104 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.8795   -2.9922    3.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5108   -0.7594    4.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3586   -2.7250    4.1835 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9113   -0.5087    1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4617    0.6530    1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4380   -1.0179    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5645   -0.2698   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3806   -0.8543   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3178   -0.1031   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4187   -1.8701   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1181   -2.3566    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7367   -2.9213    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4918   -0.5091   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220   -1.1980   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7504   -2.3062    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1862   -2.1452    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5475    0.4157    0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6173    1.3070    3.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589    1.9065    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2222    3.1925    2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765    1.7090    3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681    3.3165    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    2.0278   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2255    3.5051   -2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1683    1.0935   -3.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511    0.5551   -3.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492   -0.6099   -3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285   -0.1801    0.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705   -0.2331   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045   -1.2891   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7027    1.0710   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    1.6619   -1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023    1.9603   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084   -1.4340    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922    1.7752    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3329    0.4263   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1274    0.8589    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4473    0.0526    1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5759    2.5590   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3253    1.0408   -5.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8873    2.4840   -4.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0269   -2.1655   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1226   -0.4884   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3135   -2.1899   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.5481    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2555   -0.5774    5.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6703   -2.2579    4.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  3 59  1  0
  3 60  1  0
  3 61  1  0
  4 62  1  0
  4 63  1  0
  8 64  1  0
  8 65  1  0
  9 66  1  0
  9 67  1  0
 10 68  1  0
 13 69  1  0
 13 70  1  0
 14 71  1  0
 14 72  1  0
 15 73  1  0
 18 74  1  1
 19 75  1  0
 21 76  1  0
 21 77  1  0
 21 78  1  0
 22 79  1  0
 22 80  1  0
 22 81  1  0
 23 82  1  0
 23 83  1  0
 27 84  1  0
 31 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  1
 36 89  1  1
 38 90  1  0
 42 91  1  0
 42 92  1  0
 44 93  1  0
 47 94  1  6
 48 95  1  0
 49 96  1  6
 53 97  1  0
 54 98  1  0
M  END


  Mrv1652305132019432D          

 54 56  0  0  1  0            999 V2000
   26.6053   -2.0449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.9379   -1.5600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3504   -2.8295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.2704   -2.0449    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.5254   -2.8295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.8353   -3.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8596   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6024   -6.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1451   -6.4984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4307   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7162   -6.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1735   -4.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4307   -5.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1735   -4.0234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7445   -4.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4590   -3.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8880   -2.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7610   -1.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1735   -2.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5859   -1.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4590   -2.7858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7445   -2.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6024   -2.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2524   -2.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9023   -2.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4274   -1.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4274   -3.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0774   -1.5483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0774   -3.1983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4274   -2.3733    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.0774   -2.3733    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.4858   -1.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0404   -3.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2154   -4.3220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8654   -4.3220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0404   -4.3220    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.0404   -5.1470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3899   -1.7900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0031   -2.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7255   -1.0363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7175   -1.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0031   -3.1669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5460   -1.1225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4320   -2.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7176   -3.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4320   -3.1669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1464   -1.9294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3169   -6.0859    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.7458   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1747   -6.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0313   -6.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0313   -7.3234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4603   -6.4984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4603   -7.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 51  1  0  0  0  0
 51 49  1  0  0  0  0
 49 53  1  0  0  0  0
 53 50  1  0  0  0  0
 51 52  2  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001113

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C26H44N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21+,25-/m1/s1

> <INCHI_KEY>
UYVZIWWBJMYRCD-ZMHDXICWSA-N

> <FORMULA>
C26H44N7O17P3S

> <MOLECULAR_WEIGHT>
851.651

> <EXACT_MASS>
851.172723243

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
77.00735349735763

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
-4.187003273826817

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8869907618463242

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8192081380192442

> <JCHEM_PKA_STRONGEST_BASIC>
6.483432718665319

> <JCHEM_POLAR_SURFACE_AREA>
370.61000000000007

> <JCHEM_REFRACTIVITY>
187.0279000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001113
     RDKit          3D
Isovaleryl-CoA
 98100  0  0  0  0  0  0  0  0999 V2000
   10.8185   -0.3874    1.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3096   -0.9765    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4062   -0.9810   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8207   -2.3725    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3049   -3.1290   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9792   -4.0954   -1.2678 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7401   -2.8058   -1.6571 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9198   -1.4397   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1882   -1.7119    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9538   -0.3760    0.9448 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.0532    1.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3426   -0.8359    2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1896    1.3793    2.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9432    2.1681    2.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    2.3600    1.2856 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    2.5396    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4356    3.2087    0.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    2.0675   -1.2302 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4565    3.0094   -2.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.7358   -1.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871    0.3930   -2.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790   -0.3173   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705    0.8211   -1.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235   -0.3887   -1.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328   -0.2087   -1.3153 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1334   -0.9909   -2.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604    1.3524   -1.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -1.0054    0.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1418    0.0352    1.4016 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.8462    1.4495    1.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453   -0.5421    2.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -0.0844    1.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5238    0.7193    0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0032    0.5371    1.3852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8790    1.2186    0.5917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8611    0.2719    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6320    0.7934   -0.9317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4373    1.8818   -1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3669    2.0670   -2.5471 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2423    1.0028   -2.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3510    0.6834   -3.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9041    1.4521   -4.2108 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0069   -0.5260   -2.8552 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5039   -1.2210   -1.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4343   -0.9399   -1.1608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7351    0.2083   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9384   -0.8693   -0.1851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5362   -2.0174   -0.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2902   -0.9790    1.2131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3112   -1.2181    2.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9898   -1.9718    3.5104 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.8795   -2.9922    3.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5108   -0.7594    4.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3586   -2.7250    4.1835 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9113   -0.5087    1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4617    0.6530    1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4380   -1.0179    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5645   -0.2698   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3806   -0.8543   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3178   -0.1031   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4187   -1.8701   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1181   -2.3566    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7367   -2.9213    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4918   -0.5091   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220   -1.1980   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7504   -2.3062    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1862   -2.1452    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5475    0.4157    0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6173    1.3070    3.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589    1.9065    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2222    3.1925    2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765    1.7090    3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681    3.3165    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    2.0278   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2255    3.5051   -2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1683    1.0935   -3.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511    0.5551   -3.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492   -0.6099   -3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285   -0.1801    0.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705   -0.2331   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045   -1.2891   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7027    1.0710   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    1.6619   -1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023    1.9603   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084   -1.4340    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922    1.7752    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3329    0.4263   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1274    0.8589    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4473    0.0526    1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5759    2.5590   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3253    1.0408   -5.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8873    2.4840   -4.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0269   -2.1655   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1226   -0.4884   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3135   -2.1899   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.5481    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2555   -0.5774    5.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6703   -2.2579    4.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
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 29 30  2  0
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 29 32  1  0
 32 33  1  0
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 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
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 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
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  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
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  4 62  1  0
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  8 64  1  0
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  9 67  1  0
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 18 74  1  1
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 27 84  1  0
 31 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  1
 36 89  1  1
 38 90  1  0
 42 91  1  0
 42 92  1  0
 44 93  1  0
 47 94  1  6
 48 95  1  0
 49 96  1  6
 53 97  1  0
 54 98  1  0
M  END

HEADER    PROTEIN                                 13-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-MAY-20         0                                  
HETATM    1  C   UNK     0      49.663  -3.817   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      48.417  -2.912   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      49.187  -5.282   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      47.171  -3.817   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.647  -5.282   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      50.093  -6.528   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      37.071 -11.360   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.458 -12.130   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      35.738 -12.130   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      34.404 -11.360   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      33.070 -12.130   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      35.791  -9.050   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.404  -9.820   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      35.791  -7.510   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      33.123  -7.510   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      34.457  -6.740   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.124  -5.200   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.021  -3.097   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.791  -4.430   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.560  -3.097   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.457  -5.200   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      33.123  -4.430   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      38.458  -4.430   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      41.538  -4.430   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      44.618  -4.430   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      39.998  -2.890   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      39.998  -5.970   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      43.078  -2.890   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      43.078  -5.970   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      39.998  -4.430   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      43.078  -4.430   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      45.707  -3.341   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      46.742  -6.528   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      45.202  -8.068   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      48.282  -8.068   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      46.742  -8.068   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      46.742  -9.608   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      51.128  -3.341   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      52.272  -4.372   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      51.754  -1.934   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      53.606  -3.602   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      52.272  -5.912   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      53.286  -2.095   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      54.940  -4.372   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      53.606  -6.682   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      54.940  -5.912   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      56.273  -3.602   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      39.792 -11.360   0.000  0.00  0.00           S+0
HETATM   49  C   UNK     0      42.459 -11.360   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      45.126 -11.360   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      41.125 -12.130   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      41.125 -13.670   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      43.793 -12.130   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      43.793 -13.670   0.000  0.00  0.00           C+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   48                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   51                                                       
CONECT   49   51   53                                                       
CONECT   50   53                                                            
CONECT   51   48   49   52                                                  
CONECT   52   51                                                            
CONECT   53   49   50   54                                                  
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

COMPND    HMDB0001113
HETATM    1  C1  UNL     1      10.819  -0.387   1.354  1.00  0.00           C  
HETATM    2  C2  UNL     1      10.310  -0.977   0.037  1.00  0.00           C  
HETATM    3  C3  UNL     1      11.406  -0.981  -1.009  1.00  0.00           C  
HETATM    4  C4  UNL     1       9.821  -2.372   0.291  1.00  0.00           C  
HETATM    5  C5  UNL     1       9.305  -3.129  -0.816  1.00  0.00           C  
HETATM    6  O1  UNL     1       9.979  -4.095  -1.268  1.00  0.00           O  
HETATM    7  S1  UNL     1       7.740  -2.806  -1.657  1.00  0.00           S  
HETATM    8  C6  UNL     1       6.920  -1.440  -0.933  1.00  0.00           C  
HETATM    9  C7  UNL     1       6.188  -1.712   0.384  1.00  0.00           C  
HETATM   10  N1  UNL     1       5.954  -0.376   0.945  1.00  0.00           N  
HETATM   11  C8  UNL     1       5.097  -0.053   1.989  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.343  -0.836   2.534  1.00  0.00           O  
HETATM   13  C9  UNL     1       5.190   1.379   2.427  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.943   2.168   2.503  1.00  0.00           C  
HETATM   15  N2  UNL     1       3.245   2.360   1.286  1.00  0.00           N  
HETATM   16  C11 UNL     1       2.596   2.540   0.159  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.436   3.209   0.078  1.00  0.00           O  
HETATM   18  C12 UNL     1       2.978   2.067  -1.230  1.00  0.00           C  
HETATM   19  O4  UNL     1       2.457   3.009  -2.134  1.00  0.00           O  
HETATM   20  C13 UNL     1       2.340   0.736  -1.535  1.00  0.00           C  
HETATM   21  C14 UNL     1       2.687   0.393  -2.984  1.00  0.00           C  
HETATM   22  C15 UNL     1       2.979  -0.317  -0.643  1.00  0.00           C  
HETATM   23  C16 UNL     1       0.870   0.821  -1.300  1.00  0.00           C  
HETATM   24  O5  UNL     1       0.223  -0.389  -1.573  1.00  0.00           O  
HETATM   25  P1  UNL     1      -1.433  -0.209  -1.315  1.00  0.00           P  
HETATM   26  O6  UNL     1      -2.133  -0.991  -2.455  1.00  0.00           O  
HETATM   27  O7  UNL     1      -1.960   1.352  -1.436  1.00  0.00           O  
HETATM   28  O8  UNL     1      -1.952  -1.005   0.093  1.00  0.00           O  
HETATM   29  P2  UNL     1      -2.142   0.035   1.402  1.00  0.00           P  
HETATM   30  O9  UNL     1      -1.846   1.450   1.060  1.00  0.00           O  
HETATM   31  O10 UNL     1      -1.145  -0.542   2.664  1.00  0.00           O  
HETATM   32  O11 UNL     1      -3.787  -0.084   1.894  1.00  0.00           O  
HETATM   33  C17 UNL     1      -4.524   0.719   0.988  1.00  0.00           C  
HETATM   34  C18 UNL     1      -6.003   0.537   1.385  1.00  0.00           C  
HETATM   35  O12 UNL     1      -6.879   1.219   0.592  1.00  0.00           O  
HETATM   36  C19 UNL     1      -7.861   0.272   0.170  1.00  0.00           C  
HETATM   37  N3  UNL     1      -8.632   0.793  -0.932  1.00  0.00           N  
HETATM   38  C20 UNL     1      -8.437   1.882  -1.610  1.00  0.00           C  
HETATM   39  N4  UNL     1      -9.367   2.067  -2.547  1.00  0.00           N  
HETATM   40  C21 UNL     1     -10.242   1.003  -2.485  1.00  0.00           C  
HETATM   41  C22 UNL     1     -11.351   0.683  -3.203  1.00  0.00           C  
HETATM   42  N5  UNL     1     -11.904   1.452  -4.211  1.00  0.00           N  
HETATM   43  N6  UNL     1     -12.007  -0.526  -2.855  1.00  0.00           N  
HETATM   44  C23 UNL     1     -11.504  -1.221  -1.879  1.00  0.00           C  
HETATM   45  N7  UNL     1     -10.434  -0.940  -1.161  1.00  0.00           N  
HETATM   46  C24 UNL     1      -9.735   0.208  -1.434  1.00  0.00           C  
HETATM   47  C25 UNL     1      -6.938  -0.869  -0.185  1.00  0.00           C  
HETATM   48  O13 UNL     1      -7.536  -2.017  -0.597  1.00  0.00           O  
HETATM   49  C26 UNL     1      -6.290  -0.979   1.213  1.00  0.00           C  
HETATM   50  O14 UNL     1      -7.311  -1.218   2.083  1.00  0.00           O  
HETATM   51  P3  UNL     1      -6.990  -1.972   3.510  1.00  0.00           P  
HETATM   52  O15 UNL     1      -5.880  -2.992   3.343  1.00  0.00           O  
HETATM   53  O16 UNL     1      -6.511  -0.759   4.635  1.00  0.00           O  
HETATM   54  O17 UNL     1      -8.359  -2.725   4.183  1.00  0.00           O  
HETATM   55  H1  UNL     1      11.911  -0.509   1.342  1.00  0.00           H  
HETATM   56  H2  UNL     1      10.462   0.653   1.416  1.00  0.00           H  
HETATM   57  H3  UNL     1      10.438  -1.018   2.185  1.00  0.00           H  
HETATM   58  H4  UNL     1       9.565  -0.270  -0.345  1.00  0.00           H  
HETATM   59  H5  UNL     1      12.381  -0.854  -0.463  1.00  0.00           H  
HETATM   60  H6  UNL     1      11.318  -0.103  -1.678  1.00  0.00           H  
HETATM   61  H7  UNL     1      11.419  -1.870  -1.658  1.00  0.00           H  
HETATM   62  H8  UNL     1       9.118  -2.357   1.165  1.00  0.00           H  
HETATM   63  H9  UNL     1      10.737  -2.921   0.698  1.00  0.00           H  
HETATM   64  H10 UNL     1       7.492  -0.509  -0.912  1.00  0.00           H  
HETATM   65  H11 UNL     1       6.022  -1.198  -1.665  1.00  0.00           H  
HETATM   66  H12 UNL     1       6.750  -2.306   1.072  1.00  0.00           H  
HETATM   67  H13 UNL     1       5.186  -2.145   0.157  1.00  0.00           H  
HETATM   68  H14 UNL     1       6.547   0.416   0.545  1.00  0.00           H  
HETATM   69  H15 UNL     1       5.617   1.307   3.502  1.00  0.00           H  
HETATM   70  H16 UNL     1       5.959   1.907   1.862  1.00  0.00           H  
HETATM   71  H17 UNL     1       4.222   3.192   2.971  1.00  0.00           H  
HETATM   72  H18 UNL     1       3.276   1.709   3.283  1.00  0.00           H  
HETATM   73  H19 UNL     1       2.468   3.317   1.921  1.00  0.00           H  
HETATM   74  H20 UNL     1       4.071   2.028  -1.349  1.00  0.00           H  
HETATM   75  H21 UNL     1       3.225   3.505  -2.540  1.00  0.00           H  
HETATM   76  H22 UNL     1       2.168   1.094  -3.681  1.00  0.00           H  
HETATM   77  H23 UNL     1       3.751   0.555  -3.157  1.00  0.00           H  
HETATM   78  H24 UNL     1       2.349  -0.610  -3.239  1.00  0.00           H  
HETATM   79  H25 UNL     1       2.728  -0.180   0.414  1.00  0.00           H  
HETATM   80  H26 UNL     1       4.071  -0.233  -0.856  1.00  0.00           H  
HETATM   81  H27 UNL     1       2.605  -1.289  -1.069  1.00  0.00           H  
HETATM   82  H28 UNL     1       0.703   1.071  -0.219  1.00  0.00           H  
HETATM   83  H29 UNL     1       0.485   1.662  -1.900  1.00  0.00           H  
HETATM   84  H30 UNL     1      -1.302   1.960  -1.109  1.00  0.00           H  
HETATM   85  H31 UNL     1      -0.808  -1.434   2.462  1.00  0.00           H  
HETATM   86  H32 UNL     1      -4.192   1.775   1.193  1.00  0.00           H  
HETATM   87  H33 UNL     1      -4.333   0.426  -0.050  1.00  0.00           H  
HETATM   88  H34 UNL     1      -6.127   0.859   2.424  1.00  0.00           H  
HETATM   89  H35 UNL     1      -8.447   0.053   1.062  1.00  0.00           H  
HETATM   90  H36 UNL     1      -7.576   2.559  -1.394  1.00  0.00           H  
HETATM   91  H37 UNL     1     -12.325   1.041  -5.073  1.00  0.00           H  
HETATM   92  H38 UNL     1     -11.887   2.484  -4.173  1.00  0.00           H  
HETATM   93  H39 UNL     1     -12.027  -2.166  -1.603  1.00  0.00           H  
HETATM   94  H40 UNL     1      -6.123  -0.488  -0.856  1.00  0.00           H  
HETATM   95  H41 UNL     1      -8.313  -2.190  -0.024  1.00  0.00           H  
HETATM   96  H42 UNL     1      -5.387  -1.548   1.267  1.00  0.00           H  
HETATM   97  H43 UNL     1      -7.255  -0.577   5.270  1.00  0.00           H  
HETATM   98  H44 UNL     1      -8.670  -2.258   4.987  1.00  0.00           H  
CONECT    1    2   55   56   57
CONECT    2    3    4   58
CONECT    3   59   60   61
CONECT    4    5   62   63
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   64   65
CONECT    9   10   66   67
CONECT   10   11   68
CONECT   11   12   12   13
CONECT   13   14   69   70
CONECT   14   15   71   72
CONECT   15   16   73
CONECT   16   17   17   18
CONECT   18   19   20   74
CONECT   19   75
CONECT   20   21   22   23
CONECT   21   76   77   78
CONECT   22   79   80   81
CONECT   23   24   82   83
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   84
CONECT   28   29
CONECT   29   30   30   31   32
CONECT   31   85
CONECT   32   33
CONECT   33   34   86   87
CONECT   34   35   49   88
CONECT   35   36
CONECT   36   37   47   89
CONECT   37   38   46
CONECT   38   39   39   90
CONECT   39   40
CONECT   40   41   41   46
CONECT   41   42   43
CONECT   42   91   92
CONECT   43   44   44
CONECT   44   45   93
CONECT   45   46   46
CONECT   47   48   49   94
CONECT   48   95
CONECT   49   50   96
CONECT   50   51
CONECT   51   52   52   53   54
CONECT   53   97
CONECT   54   98
END

HMDB0001113
     RDKit          3D
Isovaleryl-CoA
 98100  0  0  0  0  0  0  0  0999 V2000
   10.8185   -0.3874    1.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3096   -0.9765    0.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4062   -0.9810   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8207   -2.3725    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3049   -3.1290   -0.8163 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9792   -4.0954   -1.2678 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7401   -2.8058   -1.6571 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9198   -1.4397   -0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1882   -1.7119    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9538   -0.3760    0.9448 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0971   -0.0532    1.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3426   -0.8359    2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1896    1.3793    2.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9432    2.1681    2.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450    2.3600    1.2856 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958    2.5396    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4356    3.2087    0.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784    2.0675   -1.2302 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4565    3.0094   -2.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3397    0.7358   -1.5349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6871    0.3930   -2.9840 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790   -0.3173   -0.6427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705    0.8211   -1.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235   -0.3887   -1.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328   -0.2087   -1.3153 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1334   -0.9909   -2.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9604    1.3524   -1.4364 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -1.0054    0.0932 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1418    0.0352    1.4016 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.8462    1.4495    1.0598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453   -0.5421    2.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -0.0844    1.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5238    0.7193    0.9882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0032    0.5371    1.3852 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8790    1.2186    0.5917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8611    0.2719    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.6320    0.7934   -0.9317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4373    1.8818   -1.6096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3669    2.0670   -2.5471 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2423    1.0028   -2.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3510    0.6834   -3.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9041    1.4521   -4.2108 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0069   -0.5260   -2.8552 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5039   -1.2210   -1.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4343   -0.9399   -1.1608 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7351    0.2083   -1.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9384   -0.8693   -0.1851 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5362   -2.0174   -0.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2902   -0.9790    1.2131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3112   -1.2181    2.0827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9898   -1.9718    3.5104 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.8795   -2.9922    3.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5108   -0.7594    4.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3586   -2.7250    4.1835 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9113   -0.5087    1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4617    0.6530    1.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4380   -1.0179    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5645   -0.2698   -0.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3806   -0.8543   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3178   -0.1031   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4187   -1.8701   -1.6583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1181   -2.3566    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7367   -2.9213    0.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4918   -0.5091   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220   -1.1980   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7504   -2.3062    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1862   -2.1452    0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5475    0.4157    0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6173    1.3070    3.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589    1.9065    1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2222    3.1925    2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765    1.7090    3.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4681    3.3165    1.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    2.0278   -1.3490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2255    3.5051   -2.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1683    1.0935   -3.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7511    0.5551   -3.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3492   -0.6099   -3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285   -0.1801    0.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0705   -0.2331   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045   -1.2891   -1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7027    1.0710   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    1.6619   -1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3023    1.9603   -1.1093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084   -1.4340    2.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1922    1.7752    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3329    0.4263   -0.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1274    0.8589    2.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4473    0.0526    1.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5759    2.5590   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3253    1.0408   -5.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8873    2.4840   -4.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0269   -2.1655   -1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1226   -0.4884   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3135   -2.1899   -0.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3871   -1.5481    1.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2555   -0.5774    5.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6703   -2.2579    4.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  3 59  1  0
  3 60  1  0
  3 61  1  0
  4 62  1  0
  4 63  1  0
  8 64  1  0
  8 65  1  0
  9 66  1  0
  9 67  1  0
 10 68  1  0
 13 69  1  0
 13 70  1  0
 14 71  1  0
 14 72  1  0
 15 73  1  0
 18 74  1  1
 19 75  1  0
 21 76  1  0
 21 77  1  0
 21 78  1  0
 22 79  1  0
 22 80  1  0
 22 81  1  0
 23 82  1  0
 23 83  1  0
 27 84  1  0
 31 85  1  0
 33 86  1  0
 33 87  1  0
 34 88  1  1
 36 89  1  1
 38 90  1  0
 42 91  1  0
 42 92  1  0
 44 93  1  0
 47 94  1  6
 48 95  1  0
 49 96  1  6
 53 97  1  0
 54 98  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Methylbutanoyl-CoA	ChEBI
3-Methylbutanoyl-coenzyme A	ChEBI
3-Methylbutyryl-CoA	ChEBI
3-Methylbutyryl-coenzyme A	ChEBI
beta-Methylbutanoyl-CoA	ChEBI
beta-Methylbutanoyl-coenzyme A	ChEBI
beta-Methylbutyryl-CoA	ChEBI
beta-Methylbutyryl-coenzyme A	ChEBI
Isovaleryl-coenzyme A	ChEBI
b-Methylbutanoyl-CoA	Generator
Β-methylbutanoyl-CoA	Generator
b-Methylbutanoyl-coenzyme A	Generator
Β-methylbutanoyl-coenzyme A	Generator
b-Methylbutyryl-CoA	Generator
Β-methylbutyryl-CoA	Generator
b-Methylbutyryl-coenzyme A	Generator
Β-methylbutyryl-coenzyme A	Generator
Isovaleryl coenzyme A	HMDB
Isovaleryl-CoA	HMDB

Chemical Formula

C₂₆H₄₄N₇O₁₇P₃S

Average Molecular Weight

851.651

Monoisotopic Molecular Weight

851.172723243

IUPAC Name

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid

Traditional Name

(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-methylbutanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanimidic acid

CAS Registry Number

6244-91-3

SMILES

CC(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C26H44N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21+,25-/m1/s1

InChI Key

UYVZIWWBJMYRCD-ZMHDXICWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methylbutanoyl-CoA (CHEBI:15487 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.7 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-4.2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.48	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	370.61 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	187.03 m³·mol⁻¹	ChemAxon
Polarizability	77.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	208.712	30932474
DeepCCS	[M-H]-	207.059	30932474
DeepCCS	[M-2H]-	241.092	30932474
DeepCCS	[M+Na]+	215.728	30932474
AllCCS	[M+H]+	259.5	32859911
AllCCS	[M+H-H2O]+	260.0	32859911
AllCCS	[M+NH4]+	259.1	32859911
AllCCS	[M+Na]+	259.0	32859911
AllCCS	[M-H]-	253.3	32859911
AllCCS	[M+Na-2H]-	257.7	32859911
AllCCS	[M+HCOO]-	262.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.63 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1919 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	489.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1324.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	155.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	106.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	83.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	372.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	440.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	782.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	665.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	376.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	688.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	213.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	298.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	356.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isovaleryl-CoA	CC(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N	5721.0	Standard polar	33892256
Isovaleryl-CoA	CC(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N	4342.1	Standard non polar	33892256
Isovaleryl-CoA	CC(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N	6376.1	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Valine, leucine and isoleucine degradation	Not Available
Beta-Ketothiolase Deficiency		Not Available
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency		Not Available
Propionic Acidemia		Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022430

KNApSAcK ID

Not Available

Chemspider ID

145017

KEGG Compound ID

C02939

BioCyc ID

ISOVALERYL-COA

BiGG ID

Not Available

Wikipedia Link

Isovaleryl-CoA

METLIN ID

Not Available

PubChem Compound

165435

PDB ID

Not Available

ChEBI ID

15487

Food Biomarker Ontology

Not Available

VMH ID

IVCOA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Valentin, Henry E.; Steinbuechel, Alexander. Application of enzymically synthesized short-chain-length hydroxy fatty acid coenzyme A thioesters for assay of polyhydroxyalkanoic acid synthases. Applied Microbiology and Biotechnology (1994), 40(5), 699-709.

Material Safety Data Sheet (MSDS)

Not Available

General References

Vockley J, Ensenauer R: Isovaleric acidemia: new aspects of genetic and phenotypic heterogeneity. Am J Med Genet C Semin Med Genet. 2006 May 15;142C(2):95-103. [PubMed:16602101 ]

Only showing the first 10 proteins. There are 112 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 3-ketoacyl-CoA thiolase, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:: ACAA2
Uniprot ID:: P42765
Molecular weight:: 41923.82

Enzyme Details

2. 3-ketoacyl-CoA thiolase, peroxisomal

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: ACAA1
Uniprot ID:: P09110
Molecular weight:: 34664.46

Enzyme Details

3. Trifunctional enzyme subunit beta, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: HADHB
Uniprot ID:: P55084
Molecular weight:: 51293.955

Enzyme Details

4. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:: ALDH6A1
Uniprot ID:: Q02252
Molecular weight:: 57839.31

Enzyme Details

5. Long-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADL
Uniprot ID:: P28330
Molecular weight:: 47655.275

Enzyme Details

6. Short-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADS
Uniprot ID:: P16219
Molecular weight:: 44296.705

Enzyme Details

7. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:: ACADM
Uniprot ID:: P11310
Molecular weight:: 46587.98

Reactions

Isovaleryl-CoA + FAD → 3-Methylcrotonyl-CoA + FADH	details

Enzyme Details

8. Peroxisomal acyl-coenzyme A oxidase 1

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:: ACOX1
Uniprot ID:: Q15067
Molecular weight:: 70135.205

Enzyme Details

9. Peroxisomal acyl-coenzyme A oxidase 2

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:: ACOX2
Uniprot ID:: Q99424
Molecular weight:: 76826.14

Enzyme Details

10. Isovaleryl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: IVD
Uniprot ID:: P26440
Molecular weight:: 43055.325

Reactions

Isovaleryl-CoA + electron-transfer flavoprotein → 3-Methylcrotonyl-CoA + reduced electron-transfer flavoprotein	details
Isovaleryl-CoA + FAD → 3-Methylcrotonyl-CoA + FADH	details

Transporters

Enzyme Details

1. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Only showing the first 10 proteins. There are 112 proteins in total.

Show all enzymes and transporters

Showing metabocard for Isovaleryl-CoA (HMDB0001113)

MOL for HMDB0001113 (Isovaleryl-CoA)

3D MOL for HMDB0001113 (Isovaleryl-CoA)

3D SDF for HMDB0001113 (Isovaleryl-CoA)

3D-SDF for HMDB0001113 (Isovaleryl-CoA)

PDB for HMDB0001113 (Isovaleryl-CoA)

3D PDB for HMDB0001113 (Isovaleryl-CoA)

SMILES for HMDB0001113 (Isovaleryl-CoA)

INCHI for HMDB0001113 (Isovaleryl-CoA)

Structure for HMDB0001113 (Isovaleryl-CoA)

3D Structure for HMDB0001113 (Isovaleryl-CoA)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Enzymes

Reactions

Reactions

Transporters