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Showing metabocard for Pteroyltriglutamic acid (HMDB0001902)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-03-09 15:41:08 UTC
Update Date2021-09-14 15:42:00 UTC
HMDB IDHMDB0001902
Secondary Accession Numbers
  • HMDB01902
Metabolite Identification
Common NamePteroyltriglutamic acid
DescriptionPteroyltriglutamic acid is a crystalline conjugate of folic acid containing three molecules of glutamic acid instead of one and having the general properties of a polypeptide. As a measure of enterocyte function, the deconjugation of Pteroylpolyglutamic acid (pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid) to folic acid and subsequent active absorption was measured in 19 patients with progressive systemic sclerosis and compared with 14 controls. The absorption step of folic acid was identical in the two groups, while deconjugation of pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid was significantly decreased in the patients with progressive systemic sclerosis. This observation suggests a primary epithelial defect of the small intestine in patients with progressive systemic sclerosis. (PMID 3583071 ). Glutamyl hydrolase cleaves the poly-g-glutamate chain folate and antifolate poly-g-glutamates. Its cellular location is lysosomal with large amts. of the enzyme constitutively secreted. The highest levels of glutamyl hydrolase mRNA in humans is found in the liver and kidney (PMID:10598552 ).
Structure
Data?1582752215
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001902 (Pteroyltriglutamic acid)


  Mrv1652305271900272D          

 50 52  0  0  0  0            999 V2000
   19.5156   -3.4482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0990   -6.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3770   -4.6938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6927  -12.5340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 48 50  2  0  0  0  0
M  END
Download

3D MOL for HMDB0001902 (Pteroyltriglutamic acid)

HMDB0001902
     RDKit          3D
Pteroyltriglutamic acid
 83 85  0  0  0  0  0  0  0  0999 V2000
   11.2162    5.2383    1.2776 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9222    3.9650    0.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8780    3.3261   -0.0455 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6671    2.0764   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5688    1.5667   -1.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4530    1.5058   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2092    0.2330   -0.8425 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0362   -0.3941   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
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 46 81  1  0
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 50 83  1  0
M  END
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3D SDF for HMDB0001902 (Pteroyltriglutamic acid)


  Mrv1652305271900272D          

 50 52  0  0  0  0            999 V2000
   19.5156   -3.4482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0990   -6.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4021  -10.8621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3770   -4.6938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9445   -3.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8182   -7.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6924  -12.1022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0962   -5.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2412   -6.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9636   -8.3926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5411  -10.0481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0644  -11.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9509   -5.0926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3924   -8.3871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2603  -11.2828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6927  -12.5340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6354  -13.7942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0644  -13.7942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3499  -12.5567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5164  -12.1156    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5164  -13.8228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2347   -4.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3893   -7.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9731  -10.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5219   -5.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6733   -7.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9700  -10.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8059   -4.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6702   -6.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6828   -9.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9767  -12.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2316   -3.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1022   -7.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6891  -11.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0930   -5.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9540   -5.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6797   -8.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5442  -10.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3499  -13.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0644  -12.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7788  -13.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2637  -12.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4056  -12.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7788  -12.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8313  -11.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2637  -13.3989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1216  -12.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4024  -11.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8345  -12.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1153  -10.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 32  1  0  0  0  0
  2 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  0  0  0  0
  5 32  2  0  0  0  0
  6 33  2  0  0  0  0
  7 34  2  0  0  0  0
  8 35  2  0  0  0  0
  9 36  2  0  0  0  0
 10 37  2  0  0  0  0
 11 38  2  0  0  0  0
 12 40  2  0  0  0  0
 13 22  1  0  0  0  0
 13 36  1  0  0  0  0
 14 23  1  0  0  0  0
 14 37  1  0  0  0  0
 15 24  1  0  0  0  0
 15 38  1  0  0  0  0
 16 31  1  0  0  0  0
 16 43  1  0  0  0  0
 17 39  1  0  0  0  0
 18 39  1  0  0  0  0
 18 41  1  0  0  0  0
 19 39  2  0  0  0  0
 19 40  1  0  0  0  0
 20 42  1  0  0  0  0
 20 44  2  0  0  0  0
 21 41  2  0  0  0  0
 21 46  1  0  0  0  0
 22 25  1  0  0  0  0
 22 32  1  0  0  0  0
 23 26  1  0  0  0  0
 23 33  1  0  0  0  0
 24 27  1  0  0  0  0
 24 34  1  0  0  0  0
 25 28  1  0  0  0  0
 26 29  1  0  0  0  0
 27 30  1  0  0  0  0
 28 35  1  0  0  0  0
 29 36  1  0  0  0  0
 30 37  1  0  0  0  0
 31 42  1  0  0  0  0
 38 45  1  0  0  0  0
 40 44  1  0  0  0  0
 41 44  1  0  0  0  0
 42 46  2  0  0  0  0
 43 47  2  0  0  0  0
 43 48  1  0  0  0  0
 45 49  2  0  0  0  0
 45 50  1  0  0  0  0
 47 49  1  0  0  0  0
 48 50  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001902

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44)

> <INCHI_KEY>
WOLQREOUPKZMEX-UHFFFAOYSA-N

> <FORMULA>
C29H33N9O12

> <MOLECULAR_WEIGHT>
699.6254

> <EXACT_MASS>
699.224867565

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
67.38399612500639

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid

> <ALOGPS_LOGP>
-0.55

> <JCHEM_LOGP>
-2.632739458357009

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.4441699685836737

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.978248041618844

> <JCHEM_PKA_STRONGEST_BASIC>
2.080712256043563

> <JCHEM_POLAR_SURFACE_AREA>
341.7899999999999

> <JCHEM_REFRACTIVITY>
167.18679999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{4-[(4-{[(2-amino-4-oxo-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001902 (Pteroyltriglutamic acid)

HMDB0001902
     RDKit          3D
Pteroyltriglutamic acid
 83 85  0  0  0  0  0  0  0  0999 V2000
   11.2162    5.2383    1.2776 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9222    3.9650    0.7003 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8780    3.3261   -0.0455 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6671    2.0764   -0.5969 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5688    1.5667   -1.2781 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4530    1.5058   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2092    0.2330   -0.8425 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0362   -0.3941   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9087   -1.8134   -1.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6736   -2.0877   -1.7375 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -2.1008   -1.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2446   -1.7026   -1.7642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0373   -1.7415   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179   -2.2026    0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6188   -2.3267    0.6673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8146   -3.0206   -0.0144 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -1.6908    1.8960 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784   -2.0869    2.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -0.9460    1.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855   -1.4688    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941   -0.5833    0.5727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5848    0.5909    1.1083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1377   -0.9620   -0.6296 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1319   -0.5948   -1.4562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1633   -0.2155   -2.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3709   -1.2408   -2.3226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6086   -0.4913   -1.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0044    0.3929   -2.8026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2695   -0.7203   -0.7797 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4355   -0.0134   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9655    1.4429   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9692    2.3263    0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4579    3.7038    0.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1046    4.6429    1.2189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1382    3.9923    0.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5311   -0.2003   -1.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7146   -1.2172   -1.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4465    0.8207   -1.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9175    0.2043   -0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8794   -0.6594    0.8640 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2543    1.3928   -0.3775 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3988   -1.9602    3.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3240   -1.4145    4.2862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386   -2.3775    4.1934 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0608   -2.6036    0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2310   -2.5420    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0975    0.2179    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3134    1.4991    0.6502 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4971    2.1118    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7428    3.3764    0.9241 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7939    5.9644    0.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8786    5.5043    2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9278   -2.5310   -0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7883   -2.1521   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6890   -2.2436   -2.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3442   -1.3790   -2.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1526   -1.3816   -1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.1606    2.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4821   -3.0182    1.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0077   -0.0440    1.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3449   -0.6962    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7700   -1.4238    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5545   -2.5374    1.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305    0.4396   -0.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7837   -1.7345   -1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8786    0.0575   -3.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7544    0.7458   -2.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042   -2.0956   -1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4973   -1.5417   -3.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8917   -1.5174   -0.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6669   -0.4040    0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7450    1.8628   -1.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0302    1.4095    0.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1506    1.9525    1.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9317    2.3614    0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8918    4.9361    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3858    0.7038   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5686    2.0025   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2407   -3.1822    3.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9535   -2.9278    1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1619   -2.8495    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1474   -0.2007    0.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0125    3.8335    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
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 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
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 33 35  1  0
 30 36  1  0
 36 37  2  0
 36 38  1  0
 24 39  1  0
 39 40  2  0
 39 41  1  0
 18 42  1  0
 42 43  2  0
 42 44  1  0
 14 45  1  0
 45 46  2  0
  8 47  2  0
 47 48  1  0
 48 49  2  0
 49 50  1  0
 50  2  1  0
 49  6  1  0
 46 11  1  0
  1 51  1  0
  1 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 12 56  1  0
 13 57  1  0
 17 58  1  0
 18 59  1  0
 19 60  1  0
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 20 62  1  0
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 23 64  1  0
 24 65  1  0
 25 66  1  0
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 29 70  1  0
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 31 72  1  0
 31 73  1  0
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 32 75  1  0
 35 76  1  0
 38 77  1  0
 41 78  1  0
 44 79  1  0
 45 80  1  0
 46 81  1  0
 47 82  1  0
 50 83  1  0
M  END
Download

PDB for HMDB0001902 (Pteroyltriglutamic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      36.429  -6.437   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      43.118 -11.801   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      41.817 -20.276   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      32.437  -8.762   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      39.096  -6.426   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      44.461 -14.106   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      40.492 -22.591   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      33.780 -11.067   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      37.784 -11.821   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      39.132 -15.666   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      36.477 -18.756   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      24.387 -21.129   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      39.108  -9.506   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      41.799 -15.656   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      37.819 -21.061   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      31.160 -23.397   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      21.719 -25.749   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      24.387 -25.749   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      23.053 -23.439   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      27.097 -22.616   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      27.097 -25.803   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      37.771  -8.741   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      41.793 -14.116   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      39.150 -20.286   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      36.441  -9.517   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      40.457 -13.351   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      39.144 -18.746   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      35.104  -8.751   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      40.451 -11.811   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      40.475 -17.971   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.823 -22.632   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      37.766  -7.201   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      43.124 -13.341   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      40.486 -21.051   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      33.774  -9.527   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      39.114 -11.046   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      40.469 -16.431   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      36.483 -20.296   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.053 -24.979   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      24.387 -22.669   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      25.720 -24.979   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      28.492 -23.407   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      32.490 -22.622   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      25.720 -23.439   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      35.152 -21.071   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      28.492 -25.011   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      33.827 -23.387   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      32.484 -21.082   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      35.158 -22.611   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      33.815 -20.307   0.000  0.00  0.00           C+0
CONECT    1   32                                                            
CONECT    2   33                                                            
CONECT    3   34                                                            
CONECT    4   35                                                            
CONECT    5   32                                                            
CONECT    6   33                                                            
CONECT    7   34                                                            
CONECT    8   35                                                            
CONECT    9   36                                                            
CONECT   10   37                                                            
CONECT   11   38                                                            
CONECT   12   40                                                            
CONECT   13   22   36                                                       
CONECT   14   23   37                                                       
CONECT   15   24   38                                                       
CONECT   16   31   43                                                       
CONECT   17   39                                                            
CONECT   18   39   41                                                       
CONECT   19   39   40                                                       
CONECT   20   42   44                                                       
CONECT   21   41   46                                                       
CONECT   22   13   25   32                                                  
CONECT   23   14   26   33                                                  
CONECT   24   15   27   34                                                  
CONECT   25   22   28                                                       
CONECT   26   23   29                                                       
CONECT   27   24   30                                                       
CONECT   28   25   35                                                       
CONECT   29   26   36                                                       
CONECT   30   27   37                                                       
CONECT   31   16   42                                                       
CONECT   32    1    5   22                                                  
CONECT   33    2    6   23                                                  
CONECT   34    3    7   24                                                  
CONECT   35    4    8   28                                                  
CONECT   36    9   13   29                                                  
CONECT   37   10   14   30                                                  
CONECT   38   11   15   45                                                  
CONECT   39   17   18   19                                                  
CONECT   40   12   19   44                                                  
CONECT   41   18   21   44                                                  
CONECT   42   20   31   46                                                  
CONECT   43   16   47   48                                                  
CONECT   44   20   40   41                                                  
CONECT   45   38   49   50                                                  
CONECT   46   21   42                                                       
CONECT   47   43   49                                                       
CONECT   48   43   50                                                       
CONECT   49   45   47                                                       
CONECT   50   45   48                                                       
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END
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3D PDB for HMDB0001902 (Pteroyltriglutamic acid)

COMPND    HMDB0001902
HETATM    1  N1  UNL     1      11.216   5.238   1.278  1.00  0.00           N  
HETATM    2  C1  UNL     1      10.922   3.965   0.700  1.00  0.00           C  
HETATM    3  N2  UNL     1      11.878   3.326  -0.045  1.00  0.00           N  
HETATM    4  C2  UNL     1      11.667   2.076  -0.597  1.00  0.00           C  
HETATM    5  O1  UNL     1      12.569   1.567  -1.278  1.00  0.00           O  
HETATM    6  C3  UNL     1      10.453   1.506  -0.352  1.00  0.00           C  
HETATM    7  N3  UNL     1      10.209   0.233  -0.842  1.00  0.00           N  
HETATM    8  C4  UNL     1       9.036  -0.394  -0.590  1.00  0.00           C  
HETATM    9  C5  UNL     1       8.909  -1.813  -1.093  1.00  0.00           C  
HETATM   10  N4  UNL     1       7.674  -2.088  -1.738  1.00  0.00           N  
HETATM   11  C6  UNL     1       6.413  -2.101  -1.155  1.00  0.00           C  
HETATM   12  C7  UNL     1       5.245  -1.703  -1.764  1.00  0.00           C  
HETATM   13  C8  UNL     1       4.037  -1.742  -1.153  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.918  -2.203   0.179  1.00  0.00           C  
HETATM   15  C10 UNL     1       2.619  -2.327   0.667  1.00  0.00           C  
HETATM   16  O2  UNL     1       1.815  -3.021  -0.014  1.00  0.00           O  
HETATM   17  N5  UNL     1       2.126  -1.691   1.896  1.00  0.00           N  
HETATM   18  C11 UNL     1       0.678  -2.087   2.079  1.00  0.00           C  
HETATM   19  C12 UNL     1      -0.035  -0.946   1.310  1.00  0.00           C  
HETATM   20  C13 UNL     1      -1.486  -1.469   1.238  1.00  0.00           C  
HETATM   21  C14 UNL     1      -2.394  -0.583   0.573  1.00  0.00           C  
HETATM   22  O3  UNL     1      -2.585   0.591   1.108  1.00  0.00           O  
HETATM   23  N6  UNL     1      -3.138  -0.962  -0.630  1.00  0.00           N  
HETATM   24  C15 UNL     1      -4.132  -0.595  -1.456  1.00  0.00           C  
HETATM   25  C16 UNL     1      -5.163  -0.216  -2.304  1.00  0.00           C  
HETATM   26  C17 UNL     1      -6.371  -1.241  -2.323  1.00  0.00           C  
HETATM   27  C18 UNL     1      -7.609  -0.491  -1.958  1.00  0.00           C  
HETATM   28  O4  UNL     1      -8.004   0.393  -2.803  1.00  0.00           O  
HETATM   29  N7  UNL     1      -8.270  -0.720  -0.780  1.00  0.00           N  
HETATM   30  C19 UNL     1      -9.436  -0.013  -0.228  1.00  0.00           C  
HETATM   31  C20 UNL     1      -8.966   1.443  -0.076  1.00  0.00           C  
HETATM   32  C21 UNL     1      -9.969   2.326   0.595  1.00  0.00           C  
HETATM   33  C22 UNL     1      -9.458   3.704   0.745  1.00  0.00           C  
HETATM   34  O5  UNL     1     -10.105   4.643   1.219  1.00  0.00           O  
HETATM   35  O6  UNL     1      -8.138   3.992   0.317  1.00  0.00           O  
HETATM   36  C23 UNL     1     -10.531  -0.200  -1.155  1.00  0.00           C  
HETATM   37  O7  UNL     1     -10.715  -1.217  -1.858  1.00  0.00           O  
HETATM   38  O8  UNL     1     -11.447   0.821  -1.284  1.00  0.00           O  
HETATM   39  C24 UNL     1      -4.917   0.204  -0.036  1.00  0.00           C  
HETATM   40  O9  UNL     1      -4.879  -0.659   0.864  1.00  0.00           O  
HETATM   41  O10 UNL     1      -5.254   1.393  -0.378  1.00  0.00           O  
HETATM   42  C25 UNL     1       0.399  -1.960   3.535  1.00  0.00           C  
HETATM   43  O11 UNL     1       1.324  -1.415   4.286  1.00  0.00           O  
HETATM   44  O12 UNL     1      -0.739  -2.377   4.193  1.00  0.00           O  
HETATM   45  C26 UNL     1       5.061  -2.604   0.816  1.00  0.00           C  
HETATM   46  C27 UNL     1       6.231  -2.542   0.157  1.00  0.00           C  
HETATM   47  C28 UNL     1       8.097   0.218   0.145  1.00  0.00           C  
HETATM   48  N8  UNL     1       8.313   1.499   0.650  1.00  0.00           N  
HETATM   49  C29 UNL     1       9.497   2.112   0.387  1.00  0.00           C  
HETATM   50  N9  UNL     1       9.743   3.376   0.924  1.00  0.00           N  
HETATM   51  H1  UNL     1      11.794   5.964   0.772  1.00  0.00           H  
HETATM   52  H2  UNL     1      10.879   5.504   2.190  1.00  0.00           H  
HETATM   53  H3  UNL     1       8.928  -2.531  -0.183  1.00  0.00           H  
HETATM   54  H4  UNL     1       9.788  -2.152  -1.663  1.00  0.00           H  
HETATM   55  H5  UNL     1       7.689  -2.244  -2.798  1.00  0.00           H  
HETATM   56  H6  UNL     1       5.344  -1.379  -2.797  1.00  0.00           H  
HETATM   57  H7  UNL     1       3.153  -1.382  -1.642  1.00  0.00           H  
HETATM   58  H8  UNL     1       2.597  -1.161   2.484  1.00  0.00           H  
HETATM   59  H9  UNL     1       0.482  -3.018   1.607  1.00  0.00           H  
HETATM   60  H10 UNL     1      -0.008  -0.044   1.938  1.00  0.00           H  
HETATM   61  H11 UNL     1       0.345  -0.696   0.359  1.00  0.00           H  
HETATM   62  H12 UNL     1      -1.770  -1.424   2.381  1.00  0.00           H  
HETATM   63  H13 UNL     1      -1.554  -2.537   1.042  1.00  0.00           H  
HETATM   64  H14 UNL     1      -2.731   0.440  -0.980  1.00  0.00           H  
HETATM   65  H15 UNL     1      -4.784  -1.735  -1.024  1.00  0.00           H  
HETATM   66  H16 UNL     1      -4.879   0.057  -3.379  1.00  0.00           H  
HETATM   67  H17 UNL     1      -5.754   0.746  -2.029  1.00  0.00           H  
HETATM   68  H18 UNL     1      -6.104  -2.096  -1.720  1.00  0.00           H  
HETATM   69  H19 UNL     1      -6.497  -1.542  -3.392  1.00  0.00           H  
HETATM   70  H20 UNL     1      -7.892  -1.517  -0.137  1.00  0.00           H  
HETATM   71  H21 UNL     1      -9.667  -0.404   0.749  1.00  0.00           H  
HETATM   72  H22 UNL     1      -8.745   1.863  -1.105  1.00  0.00           H  
HETATM   73  H23 UNL     1      -8.030   1.409   0.527  1.00  0.00           H  
HETATM   74  H24 UNL     1     -10.151   1.953   1.654  1.00  0.00           H  
HETATM   75  H25 UNL     1     -10.932   2.361   0.050  1.00  0.00           H  
HETATM   76  H26 UNL     1      -7.892   4.936   0.054  1.00  0.00           H  
HETATM   77  H27 UNL     1     -12.386   0.704  -1.514  1.00  0.00           H  
HETATM   78  H28 UNL     1      -4.569   2.002  -0.874  1.00  0.00           H  
HETATM   79  H29 UNL     1      -1.241  -3.182   3.815  1.00  0.00           H  
HETATM   80  H30 UNL     1       4.953  -2.928   1.865  1.00  0.00           H  
HETATM   81  H31 UNL     1       7.162  -2.850   0.669  1.00  0.00           H  
HETATM   82  H32 UNL     1       7.147  -0.201   0.351  1.00  0.00           H  
HETATM   83  H33 UNL     1       9.013   3.833   1.460  1.00  0.00           H  
CONECT    1    2   51   52
CONECT    2    3    3   50
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   49
CONECT    7    8
CONECT    8    9   47   47
CONECT    9   10   53   54
CONECT   10   11   55
CONECT   11   12   12   46
CONECT   12   13   56
CONECT   13   14   14   57
CONECT   14   15   45
CONECT   15   16   16   17
CONECT   17   18   58
CONECT   18   19   42   59
CONECT   19   20   60   61
CONECT   20   21   62   63
CONECT   21   22   22   23
CONECT   23   24   64
CONECT   24   25   39   65
CONECT   25   26   66   67
CONECT   26   27   68   69
CONECT   27   28   28   29
CONECT   29   30   70
CONECT   30   31   36   71
CONECT   31   32   72   73
CONECT   32   33   74   75
CONECT   33   34   34   35
CONECT   35   76
CONECT   36   37   37   38
CONECT   38   77
CONECT   39   40   40   41
CONECT   41   78
CONECT   42   43   43   44
CONECT   44   79
CONECT   45   46   46   80
CONECT   46   81
CONECT   47   48   82
CONECT   48   49   49
CONECT   49   50
CONECT   50   83
END
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SMILES for HMDB0001902 (Pteroyltriglutamic acid)

NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1
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INCHI for HMDB0001902 (Pteroyltriglutamic acid)

InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
PteroyltriglutamateGenerator
N-[N-(N-Pteroyl-L-gamma-glutamyl)-L-gamma-glutamyl]-glutamic acidHMDB
Folic acid diglutamateHMDB
N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-glutamic acidHMDB
N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-.gamma.-glutamyl]-L-.gamma.-glutamyl]- L-glutamic acidHMDB
PteropterinHMDB, MeSH
Pteroyl-gamma-triglutamic acidHMDB
Pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acidHMDB
Pteroyltri-gamma-L-glutamic acidHMDB
TeropterinMeSH, HMDB
Pteropterin, sodium saltMeSH, HMDB
Pteroyl-gamma-glutamyl-gamma-glutamylglutamic acidMeSH, HMDB
2-{[4-carboxy-4-({4-carboxy-1-hydroxy-4-[(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]butylidene}amino)-1-hydroxybutylidene]amino}pentanedioateGenerator, HMDB
Pteroyltriglutamic acidMeSH
Chemical FormulaC29H33N9O12
Average Molecular Weight699.6254
Monoisotopic Molecular Weight699.224867565
IUPAC Name2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid
Traditional Name2-(4-{4-[(4-{[(2-amino-4-oxo-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid
CAS Registry Number89-38-3
SMILES
NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1
InChI Identifier
InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44)
InChI KeyWOLQREOUPKZMEX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamic acid or derivatives
  • Glutamine or derivatives
  • Tetracarboxylic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Pterin
  • Alpha-amino acid or derivatives
  • Pteridine
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Pyrimidone
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Benzenoid
  • Pyrazine
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Amino acid
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.1 mg/mL at 5 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP-0.55ALOGPS
logP-2.6ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)2.98ChemAxon
pKa (Strongest Basic)2.08ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area341.79 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity167.19 m³·mol⁻¹ChemAxon
Polarizability67.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+258.28731661259
DarkChem[M-H]-242.64131661259
AllCCS[M+H]+237.94232859911
AllCCS[M-H]-237.00932859911
DeepCCS[M+H]+236.04730932474
DeepCCS[M-H]-233.7330932474
DeepCCS[M-2H]-266.96830932474
DeepCCS[M+Na]+241.86430932474
AllCCS[M+H]+237.932859911
AllCCS[M+H-H2O]+237.832859911
AllCCS[M+NH4]+238.132859911
AllCCS[M+Na]+238.132859911
AllCCS[M-H]-237.032859911
AllCCS[M+Na-2H]-240.032859911
AllCCS[M+HCOO]-243.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.2.58 minutes32390414
Predicted by Siyang on May 30, 202211.5365 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20228.64 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid391.5 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1197.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid181.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid96.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid158.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid79.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid305.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid429.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)993.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid709.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid308.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1135.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid263.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid302.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate411.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA334.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water578.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pteroyltriglutamic acidNC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N16160.0Standard polar33892256
Pteroyltriglutamic acidNC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N14028.8Standard non polar33892256
Pteroyltriglutamic acidNC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N17076.6Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022730
KNApSAcK IDNot Available
Chemspider ID6702
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6381
PubChem Compound6968
PDB IDNot Available
ChEBI ID554079
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hendel L, Hendel J, Joergensen I: Enterocyte function in progressive systemic sclerosis as estimated by the deconjugation of pteroyltriglutamate to folic acid. Gut. 1987 Apr;28(4):435-8. [PubMed:3583071 ]
  2. Galivan J, Ryan T, Rhee M, Yao R, Chave K: Glutamyl hydrolase: properties and pharmacologic impact. Semin Oncol. 1999 Apr;26(2 Suppl 6):33-7. [PubMed:10598552 ]