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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:00:08 UTC

HMDB ID

HMDB0001090

Secondary Accession Numbers

HMDB01090

Metabolite Identification

Common Name

(R)-5-Diphosphomevalonic acid

Description

(R)-5-Diphosphomevalonic acid, also known as mevalonate 5-diphosphate or mevalonic acid 5-pyrophosphate, belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O (R)-5-Diphosphomevalonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (R)-5-Diphosphomevalonic acid exists in all living species, ranging from bacteria to humans. In humans, (R)-5-diphosphomevalonic acid is involved in the metabolic disorder called the cholesteryl ester storage disease pathway. Outside of the human body, (R)-5-Diphosphomevalonic acid has been detected, but not quantified in, several different foods, such as pepper (c. pubescens), common pea, small-leaf lindens, chia, and sunflowers. This could make (R)-5-diphosphomevalonic acid a potential biomarker for the consumption of these foods. 5-Diphosphomevalonic acid (CAS: 1492-08-6) is a metabolic intermediate in the mevalonate pathway, catalyzed by the enzyme phosphomevalonate kinase from 5-phosphomevalonate (Wikipedia).

Structure

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

HMDB0001090
     RDKit          3D
(R)-5-Diphosphomevalonic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.6937    0.0968    2.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.3899    0.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0191    1.7436    0.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3523   -0.4063   -0.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.1150   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204   -0.9351   -1.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051   -0.7012   -1.2907 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.0238   -1.9891   -1.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    0.4984   -2.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8735   -0.2729    0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4547    0.2626    0.3453 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.4260    1.7790    0.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1785   -0.3740    1.7423 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -0.2153   -0.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5898   -0.0061    0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739    0.2674   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    1.4476   -1.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1782   -0.7689   -1.7768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351    0.5667    2.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -0.9809    2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.5515    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0979    2.2729    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -0.2004   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -1.4889   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633    0.9498   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663   -0.4816    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0192    1.3486   -1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470   -0.1158    2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4930    0.5214   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7595   -1.0739    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1619    0.6119    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356   -0.5598   -2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
M  END


  Mrv1652309152017252D          

 18 17  0  0  0  0            999 V2000
 9994.4114 9992.7647    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6970 9992.3533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1257 9992.3533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9999 9993.4814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.8248 9993.4814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9827 9992.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8400 9992.7647    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2676 9992.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4287 9993.4814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5584 9992.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.2534 9993.4814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5546 9992.7647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9990.8395 9992.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.1403 9993.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.9647 9993.4814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1264 9992.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.4113 9992.3533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1264 9993.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  1  0  0  0
 12 15  1  6  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001090

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m1/s1

> <INCHI_KEY>
SIGQQUBJQXSAMW-ZCFIWIBFSA-N

> <FORMULA>
C6H14O10P2

> <MOLECULAR_WEIGHT>
308.1169

> <EXACT_MASS>
308.006219692

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.46045514564999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid

> <ALOGPS_LOGP>
-1.17

> <JCHEM_LOGP>
-1.638744069

> <ALOGPS_LOGS>
-1.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.1625026122597153

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7759296675393568

> <JCHEM_PKA_STRONGEST_BASIC>
-2.923623985716116

> <JCHEM_POLAR_SURFACE_AREA>
170.82

> <JCHEM_REFRACTIVITY>
56.257200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mevalonate-diphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001090
     RDKit          3D
(R)-5-Diphosphomevalonic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.6937    0.0968    2.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.3899    0.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0191    1.7436    0.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3523   -0.4063   -0.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.1150   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204   -0.9351   -1.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051   -0.7012   -1.2907 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.0238   -1.9891   -1.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    0.4984   -2.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8735   -0.2729    0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4547    0.2626    0.3453 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.4260    1.7790    0.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1785   -0.3740    1.7423 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -0.2153   -0.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5898   -0.0061    0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739    0.2674   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    1.4476   -1.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1782   -0.7689   -1.7768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351    0.5667    2.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -0.9809    2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.5515    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0979    2.2729    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -0.2004   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -1.4889   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633    0.9498   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663   -0.4816    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0192    1.3486   -1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470   -0.1158    2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4930    0.5214   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7595   -1.0739    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1619    0.6119    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356   -0.5598   -2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 15-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-SEP-20         0                                  
HETATM    1  P   UNK     0    8656.2358653.161   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0    8654.9018652.393   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8657.5688652.393   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8655.4678654.499   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8657.0068654.499   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8653.5688653.161   0.000  0.00  0.00           C+0
HETATM    7  P   UNK     0    8658.9018653.161   0.000  0.00  0.00           P+0
HETATM    8  C   UNK     0    8652.2338652.393   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8658.1348654.499   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8660.2428652.389   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8659.6738654.499   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8650.9028653.161   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8649.5678652.393   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8650.1298654.499   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8651.6678654.499   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8648.2368653.161   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8646.9018652.393   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8648.2368654.699   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    2    8                                                       
CONECT    7    3    9   10   11                                             
CONECT    8    6   12                                                       
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8   13   14   15                                             
CONECT   13   12   16                                                       
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0001090
HETATM    1  C1  UNL     1      -1.694   0.097   2.075  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.133   0.390   0.670  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.019   1.744   0.423  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.352  -0.406  -0.329  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.136  -0.115  -0.265  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.720  -0.935  -1.260  1.00  0.00           O  
HETATM    7  P1  UNL     1       2.405  -0.701  -1.291  1.00  0.00           P  
HETATM    8  O3  UNL     1       3.024  -1.989  -1.743  1.00  0.00           O  
HETATM    9  O4  UNL     1       2.728   0.498  -2.418  1.00  0.00           O  
HETATM   10  O5  UNL     1       2.873  -0.273   0.264  1.00  0.00           O  
HETATM   11  P2  UNL     1       4.455   0.263   0.345  1.00  0.00           P  
HETATM   12  O6  UNL     1       4.426   1.779   0.481  1.00  0.00           O  
HETATM   13  O7  UNL     1       5.178  -0.374   1.742  1.00  0.00           O  
HETATM   14  O8  UNL     1       5.336  -0.215  -0.999  1.00  0.00           O  
HETATM   15  C5  UNL     1      -3.590  -0.006   0.534  1.00  0.00           C  
HETATM   16  C6  UNL     1      -4.074   0.267  -0.838  1.00  0.00           C  
HETATM   17  O9  UNL     1      -4.403   1.448  -1.186  1.00  0.00           O  
HETATM   18  O10 UNL     1      -4.178  -0.769  -1.777  1.00  0.00           O  
HETATM   19  H1  UNL     1      -2.435   0.567   2.785  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.678  -0.981   2.306  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.689   0.551   2.244  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.098   2.273   1.276  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.686  -0.200  -1.354  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.485  -1.489  -0.129  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.363   0.950  -0.455  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.566  -0.482   0.697  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.019   1.349  -1.979  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.647  -0.116   2.532  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.493   0.521  -1.647  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.759  -1.074   0.771  1.00  0.00           H  
HETATM   31  H13 UNL     1      -4.162   0.612   1.259  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.936  -0.560  -2.738  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   15
CONECT    3   22
CONECT    4    5   23   24
CONECT    5    6   25   26
CONECT    6    7
CONECT    7    8    8    9   10
CONECT    9   27
CONECT   10   11
CONECT   11   12   12   13   14
CONECT   13   28
CONECT   14   29
CONECT   15   16   30   31
CONECT   16   17   17   18
CONECT   18   32
END

HMDB0001090
     RDKit          3D
(R)-5-Diphosphomevalonic acid
 32 31  0  0  0  0  0  0  0  0999 V2000
   -1.6937    0.0968    2.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.3899    0.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0191    1.7436    0.4233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3523   -0.4063   -0.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.1150   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204   -0.9351   -1.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051   -0.7012   -1.2907 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.0238   -1.9891   -1.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7277    0.4984   -2.4182 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8735   -0.2729    0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4547    0.2626    0.3453 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.4260    1.7790    0.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1785   -0.3740    1.7423 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -0.2153   -0.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5898   -0.0061    0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739    0.2674   -0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    1.4476   -1.1862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1782   -0.7689   -1.7768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4351    0.5667    2.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6778   -0.9809    2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.5515    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0979    2.2729    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -0.2004   -1.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -1.4889   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3633    0.9498   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5663   -0.4816    0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0192    1.3486   -1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470   -0.1158    2.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4930    0.5214   -1.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7595   -1.0739    0.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1619    0.6119    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9356   -0.5598   -2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 11 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  9 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 18 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-5-Diphosphomevalonate	ChEBI
5-Diphosphomevalonate	HMDB
5-Diphosphomevalonic acid	HMDB
Mevalonate 5-diphosphate	HMDB
Mevalonate pyrophosphate	HMDB
Mevalonate-diphosphate	HMDB
(3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoic acid	HMDB
(R)-Diphosphomevalonic acid	HMDB
5-Pyrophosphomevalonic acid	HMDB
Mevalonic 5-pyrophosphate	HMDB
Mevalonic acid 5-diphosphate	HMDB
Mevalonic acid 5-pyrophosphate	HMDB
Mevalonic acid pyrophosphate	HMDB
Pyrophosphomevalonic acid	HMDB
(3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoate	HMDB
(R)-Diphosphomevalonate	HMDB
5-Pyrophosphomevalonate	HMDB
Mevalonate 5-pyrophosphate	HMDB
Mevalonic 5-pyrophosphic acid	HMDB
Mevalonic acid 5-diphosphic acid	HMDB
Mevalonic acid 5-pyrophosphic acid	HMDB
Mevalonic acid pyrophosphic acid	HMDB
Pyrophosphomevalonate	HMDB
(R)-5-Diphosphomevalonic acid	Generator
R-Diphosphomevalonate	HMDB

Chemical Formula

C₆H₁₄O₁₀P₂

Average Molecular Weight

308.1169

Monoisotopic Molecular Weight

308.006219692

IUPAC Name

(3R)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid

Traditional Name

mevalonate-diphosphate

CAS Registry Number

103025-21-4

SMILES

C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O

InChI Identifier

InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m1/s1

InChI Key

SIGQQUBJQXSAMW-ZCFIWIBFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxoanionic compounds

Sub Class

Organic pyrophosphates

Direct Parent

Organic pyrophosphates

Alternative Parents

Substituents

Organic pyrophosphate
Monoalkyl phosphate
Short-chain hydroxy acid
Organic phosphoric acid derivative
Fatty acid
Alkyl phosphate
Phosphoric acid ester
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carboxyalkyl phosphate (CHEBI:15899 )
Hydroxy fatty acids (LMFA01050416 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Peroxisome (HMDB: HMDB0001090)

Source

Endogenous

Endogenous (HMDB: HMDB0001090)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0120515)
Desmosterolosis (PathBank: SMP0120692)
Mevalonic Aciduria (PathBank: SMP0120794)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0120512)
Cholesteryl Ester Storage Disease (PathBank: SMP0120573)
CHILD Syndrome (PathBank: SMP0120464)
Wolman Disease (PathBank: SMP0120576)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (PathBank: SMP0120685)
Hypercholesterolemia (PathBank: SMP0120769)
Hyper-IgD Syndrome (PathBank: SMP0120574)

Metabolic pathway

Steroid Biosynthesis (PathBank: SMP0087326)
Steroid Biosynthesis (PathBank: SMP0002381)
Terpenoid Backbone Biosynthesis (PathBank: SMP0002384)
Cholesterol Biosynthesis and Metabolism CE(14:0) (PathBank: SMP0002435)
Cholesterol Biosynthesis and Metabolism CE(10:0) (PathBank: SMP0002436)
Cholesterol Biosynthesis and Metabolism CE(12:0) (PathBank: SMP0002438)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)
Cholesterol Biosynthesis and Metabolism CE(18:0) (PathBank: SMP0002441)
Cholesterol Biosynthesis and Metabolism (PathBank: SMP0070041)

Drug action pathway

Atorvastatin Action Pathway (PathBank: SMP0000131)
Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)

Role

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	8.26 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.6	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	56.26 m³·mol⁻¹	ChemAxon
Polarizability	23.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.75	31661259
DarkChem	[M-H]-	161.255	31661259
AllCCS	[M+H]+	164.528	32859911
AllCCS	[M-H]-	156.982	32859911
DeepCCS	[M+H]+	148.501	30932474
DeepCCS	[M-H]-	146.557	30932474
DeepCCS	[M-2H]-	179.795	30932474
DeepCCS	[M+Na]+	154.413	30932474
AllCCS	[M+H]+	164.5	32859911
AllCCS	[M+H-H2O]+	161.5	32859911
AllCCS	[M+NH4]+	167.3	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	157.0	32859911
AllCCS	[M+Na-2H]-	157.7	32859911
AllCCS	[M+HCOO]-	158.5	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.	3.39 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8622 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.59 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	467.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	481.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	268.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	40.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	44.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	262.9 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	293.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	631.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	587.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	76.2 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	629.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	165.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	688.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	298.0 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	612.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-5-Diphosphomevalonic acid	C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O	3795.9	Standard polar	33892256
(R)-5-Diphosphomevalonic acid	C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O	1913.2	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid	C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O	2474.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-5-Diphosphomevalonic acid,1TMS,isomer #1	C[C@@](CCOP(=O)(O)OP(=O)(O)O)(CC(=O)O)O[Si](C)(C)C	2475.2	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,1TMS,isomer #2	C[C@@](O)(CCOP(=O)(O)OP(=O)(O)O)CC(=O)O[Si](C)(C)C	2412.1	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,1TMS,isomer #3	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CC(=O)O	2431.8	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,1TMS,isomer #4	C[C@@](O)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CC(=O)O	2447.7	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TMS,isomer #1	C[C@@](CCOP(=O)(O)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2422.0	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TMS,isomer #2	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O)O[Si](C)(C)C	2440.7	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TMS,isomer #3	C[C@@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2464.7	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TMS,isomer #4	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CC(=O)O[Si](C)(C)C	2366.8	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TMS,isomer #5	C[C@@](O)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2376.7	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TMS,isomer #6	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O	2408.2	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TMS,isomer #7	C[C@@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O	2408.0	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2388.4	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2350.0	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3183.8	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #2	C[C@@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2397.8	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #2	C[C@@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2331.0	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #2	C[C@@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	3269.3	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #3	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2449.0	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #3	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2286.6	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #3	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	3048.5	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #4	C[C@@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2443.9	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #4	C[C@@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2276.7	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #4	C[C@@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	3063.4	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #5	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2372.6	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #5	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2347.0	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #5	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	3055.7	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #6	C[C@@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2384.8	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #6	C[C@@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2334.3	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #6	C[C@@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	3063.0	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #7	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O	2417.6	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #7	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O	2283.1	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TMS,isomer #7	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O	2863.7	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2436.6	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2384.1	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2902.6	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #2	C[C@@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2442.2	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #2	C[C@@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2375.8	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #2	C[C@@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2895.9	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #3	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2479.3	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #3	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2325.2	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #3	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C	2725.7	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #4	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2399.5	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #4	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2375.3	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TMS,isomer #4	C[C@@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C	2730.6	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,5TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2479.8	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,5TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2410.1	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,5TMS,isomer #1	C[C@@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2610.0	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O)OP(=O)(O)O)CC(=O)O	2692.6	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O)OP(=O)(O)O	2633.2	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@@](C)(O)CC(=O)O)OP(=O)(O)O	2661.6	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)OCC[C@@](C)(O)CC(=O)O	2674.7	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C	2839.5	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)CC(=O)O	2857.4	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O	2871.1	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2818.0	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2816.1	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(OCC[C@@](C)(O)CC(=O)O)O[Si](C)(C)C(C)(C)C	2844.8	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[C@@](C)(O)CC(=O)O	2848.8	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C	3035.7	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C	2829.4	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C	3384.9	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3036.5	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2827.0	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3459.6	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O	3063.9	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O	2774.6	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O	3264.1	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	3066.2	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	2733.7	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	3283.7	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	3010.0	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2840.1	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	3268.6	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3020.6	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2792.7	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3279.8	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3025.6	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2738.4	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3099.1	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3220.0	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2964.6	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3175.1	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3225.8	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2930.6	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3184.8	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	3263.7	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	2869.6	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O	3027.3	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3199.2	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2926.5	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3032.4	Standard polar	33892256
(R)-5-Diphosphomevalonic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3381.5	Semi standard non polar	33892256
(R)-5-Diphosphomevalonic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3069.3	Standard non polar	33892256
(R)-5-Diphosphomevalonic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3015.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-5-Diphosphomevalonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-9820000000-7d8dd5ca92f4eb0538fd	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-5-Diphosphomevalonic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dv-9243200000-6d8177d69adb810da37f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-5-Diphosphomevalonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 10V, Positive-QTOF	splash10-01wf-1391000000-a8414ad19cb44452295f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 20V, Positive-QTOF	splash10-03e9-4940000000-c856f917d05bbc77ac8a	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 40V, Positive-QTOF	splash10-01sr-9840000000-db467c852b0f7d795ece	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 10V, Negative-QTOF	splash10-0bt9-1494000000-7e72bc5c055d7b3e4f37	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 20V, Negative-QTOF	splash10-056r-7920000000-5c36505c154e9a3abebd	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 40V, Negative-QTOF	splash10-004i-9000000000-cbcfedc91b4fe71d5849	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 10V, Negative-QTOF	splash10-0a4i-0019000000-a7e7073b139ac0acc855	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 20V, Negative-QTOF	splash10-0a6r-9466000000-5ab0d4ae0def99221d8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 40V, Negative-QTOF	splash10-056s-9500000000-38a7f595bafdd824dd36	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 10V, Positive-QTOF	splash10-0a59-0938000000-9afa28886c9f8ff753e0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 20V, Positive-QTOF	splash10-001i-3940000000-53f4c41d4cec2fbfc65d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-5-Diphosphomevalonic acid 40V, Positive-QTOF	splash10-08n9-6910000000-e20806c8945d9a51ddb1	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-18	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Peroxisome

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439418

PDB ID

Not Available

ChEBI ID

15899

Food Biomarker Ontology

Not Available

VMH ID

5DPMEV

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Toth MJ, Huwyler L: Molecular cloning and expression of the cDNAs encoding human and yeast mevalonate pyrophosphate decarboxylase. J Biol Chem. 1996 Apr 5;271(14):7895-8. [PubMed:8626466 ]
Mitchell ED Jr, Avigan J: Control of phosphorylation and decarboxylation of mevalonic acid and its metabolites in cultured human fibroblasts and in rat liver in vivo. J Biol Chem. 1981 Jun 25;256(12):6170-3. [PubMed:6263908 ]
Ma D, Nutt CL, Shanehsaz P, Peng X, Louis DN, Kaetzel DM: Autocrine platelet-derived growth factor-dependent gene expression in glioblastoma cells is mediated largely by activation of the transcription factor sterol regulatory element binding protein and is associated with altered genotype and patient survival in human brain tumors. Cancer Res. 2005 Jul 1;65(13):5523-34. [PubMed:15994924 ]
Singh I, Pahan K, Khan M: Lovastatin and sodium phenylacetate normalize the levels of very long chain fatty acids in skin fibroblasts of X- adrenoleukodystrophy. FEBS Lett. 1998 Apr 24;426(3):342-6. [PubMed:9600263 ]
Wadhwa R, Yaguchi T, Hasan MK, Taira K, Kaul SC: Mortalin-MPD (mevalonate pyrophosphate decarboxylase) interactions and their role in control of cellular proliferation. Biochem Biophys Res Commun. 2003 Mar 21;302(4):735-42. [PubMed:12646231 ]
Cuthbert JA, Lipsky PE: Inhibition by 6-fluoromevalonate demonstrates that mevalonate or one of the mevalonate phosphates is necessary for lymphocyte proliferation. J Biol Chem. 1990 Oct 25;265(30):18568-75. [PubMed:2211719 ]
Hogenboom S, Tuyp JJ, Espeel M, Koster J, Wanders RJ, Waterham HR: Human mevalonate pyrophosphate decarboxylase is localized in the cytosol. Mol Genet Metab. 2004 Mar;81(3):216-24. [PubMed:14972328 ]
Andreassi JL 2nd, Dabovic K, Leyh TS: Streptococcus pneumoniae isoprenoid biosynthesis is downregulated by diphosphomevalonate: an antimicrobial target. Biochemistry. 2004 Dec 28;43(51):16461-6. [PubMed:15610040 ]
Zhou T, Daugherty M, Grishin NV, Osterman AL, Zhang H: Structure and mechanism of homoserine kinase: prototype for the GHMP kinase superfamily. Structure. 2000 Dec 15;8(12):1247-57. [PubMed:11188689 ]
Hogenboom S, Wanders RJ, Waterham HR: Cholesterol biosynthesis is not defective in peroxisome biogenesis defective fibroblasts. Mol Genet Metab. 2003 Nov;80(3):290-5. [PubMed:14680974 ]
Cuthbert JA, Lipsky PE: Negative regulation of cell proliferation by mevalonate or one of the mevalonate phosphates. J Biol Chem. 1991 Sep 25;266(27):17966-71. [PubMed:1917936 ]

Enzymes

Enzyme Details

1. Diphosphomevalonate decarboxylase

General function:: Involved in ATP binding
Specific function:: Performs the first committed step in the biosynthesis of isoprenes.
Gene Name:: MVD
Uniprot ID:: P53602
Molecular weight:: 43404.125

Reactions

Adenosine triphosphate + (R)-5-Diphosphomevalonic acid → ADP + Phosphate + Isopentenyl pyrophosphate + CO(2)	details
Adenosine triphosphate + (R)-5-Diphosphomevalonic acid → ADP + Phosphate + Isopentenyl pyrophosphate + Carbon dioxide	details

Enzyme Details

2. Phosphomevalonate kinase

General function:: Involved in phosphomevalonate kinase activity
Specific function:: Not Available
Gene Name:: PMVK
Uniprot ID:: Q15126
Molecular weight:: 21994.745

Reactions

Adenosine triphosphate + Mevalonic acid-5P → ADP + (R)-5-Diphosphomevalonic acid	details

Showing metabocard for (R)-5-Diphosphomevalonic acid (HMDB0001090)

MOL for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

3D MOL for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

3D SDF for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

3D-SDF for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

PDB for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

3D PDB for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

SMILES for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

INCHI for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

Structure for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

3D Structure for HMDB0001090 ((R)-5-Diphosphomevalonic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions