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Showing metabocard for Tetrahydropteroyltri-L-glutamic acid (HMDB0012290)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:22:25 UTC
Update Date2021-09-14 14:57:37 UTC
HMDB IDHMDB0012290
Secondary Accession Numbers
  • HMDB12290
Metabolite Identification
Common NameTetrahydropteroyltri-L-glutamic acid
DescriptionTetrahydropteroyltri-L-glutamic acid (CAS: 4227-85-4), also known as (6S)-H4pteglu3, belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof). Tetrahydropteroyltri-L-glutamic acid is a strong basic compound (based on its pKa). In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine. Tetrahydropteroyltri-L-glutamica cid exists in all living species, ranging from bacteria to humans. Tetrahydropteroyltri-L-glutamic acid is an intermediate in the synthesis of methionine by bacteria. It is a substrate for the enzyme 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase which catalyzes the reaction 5-methyltetrahydropteroyltri-L-glutamic acid + L-homocysteine = tetrahydropteroyltri-L-glutamic acid + L-methionine.
Structure
Data?1594313457
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012290 (Tetrahydropteroyltri-L-glutamic acid)


  Mrv1652303052016412D          

 50 52  0  0  0  0            999 V2000
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M  END
Download

3D MOL for HMDB0012290 (Tetrahydropteroyltri-L-glutamic acid)

HMDB0012290
     RDKit          3D
Tetrahydropteroyltri-L-glutamic acid
 87 89  0  0  0  0  0  0  0  0999 V2000
   10.2764    4.9363   -1.5513 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4231    4.4174   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D SDF for HMDB0012290 (Tetrahydropteroyltri-L-glutamic acid)


  Mrv1652303052016412D          

 50 52  0  0  0  0            999 V2000
 9991.764210000.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.7642 9999.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4766 9999.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.4766 9998.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.1890 9997.9333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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10001.762410000.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10007.479610000.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  4  5  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0012290

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N1

> <INCHI_IDENTIFIER>
InChI=1S/C29H37N9O12/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/h1-4,15-18,31,33H,5-12H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H4,30,32,37,38,44)/t15-,16-,17-,18-/m0/s1

> <INCHI_KEY>
RXWVHRYZTWZATH-XSLAGTTESA-N

> <FORMULA>
C29H37N9O12

> <MOLECULAR_WEIGHT>
703.6572

> <EXACT_MASS>
703.256167693

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
69.10149905438148

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid

> <ALOGPS_LOGP>
-1.64

> <JCHEM_LOGP>
-4.291320306633012

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.53282364234547

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5855670864294065

> <JCHEM_PKA_STRONGEST_BASIC>
3.118092401044625

> <JCHEM_POLAR_SURFACE_AREA>
340.06999999999994

> <JCHEM_REFRACTIVITY>
177.56220000000013

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0012290 (Tetrahydropteroyltri-L-glutamic acid)

HMDB0012290
     RDKit          3D
Tetrahydropteroyltri-L-glutamic acid
 87 89  0  0  0  0  0  0  0  0999 V2000
   10.2764    4.9363   -1.5513 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4231    4.4174   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3576    5.1324   -0.1262 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5314    4.6735    0.8242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5272    5.3195    1.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7514    3.4444    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8540    2.7344    0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6771    3.2037    0.0063 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1001    1.4524    1.5616 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6350    1.2863    2.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1508    1.5680    2.9014 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5154    0.4969    2.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780    0.7007    1.9509 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2609   -0.2193    1.2502 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8331   -1.3431    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0231   -2.2495    0.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6538   -2.0470   -0.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8762   -3.0448   -0.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3401   -4.2263   -0.7877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433   -2.7646   -1.4830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -3.8680   -2.1270 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4863   -3.9721   -1.8446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3170   -2.7942   -2.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7094   -3.0711   -1.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9698   -3.9480   -1.0507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7745   -2.3616   -2.5083 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1347   -2.6921   -2.0670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0643   -1.6003   -2.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7653   -0.2637   -1.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7733   -0.3305   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8821   -1.4089    0.2746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6491    0.9321    0.3774 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6354    0.9718    1.8357 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7709    2.0292    2.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2104    3.3979    2.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3373    4.4633    2.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3622    4.2102    3.3504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6075    5.8127    2.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0874    1.1922    2.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0067    1.2984    1.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3756    1.2748    3.5580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5879   -3.8869   -2.8967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8340   -4.3824   -3.7475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8393   -4.4013   -2.6854 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640   -3.7748   -3.6309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160   -2.8372   -4.1256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4291   -4.7955   -4.3693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -0.9139    0.4531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9126    0.0124    1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9256    2.8958    2.4036 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2313    5.2058   -1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9429    5.0341   -2.5223 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5058    2.6127   -0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5834    0.7121    1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7464    0.2116    3.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1661    1.9695    3.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7387    1.5220    3.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7586   -0.5133    2.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9753    0.6203    1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572    1.5311    2.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9123   -1.4965    0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4909   -3.1310   -0.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3001   -1.7870   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4652   -4.8187   -1.8618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8852   -4.8720   -2.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6529   -4.0921   -0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2127   -2.5665   -3.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8965   -1.9107   -1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6923   -1.6237   -3.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0670   -3.0661   -1.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0924   -1.4395   -3.5078 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3355   -0.0394    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2721    3.5074    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0908    6.0315    1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1963    0.7218    3.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0721   -5.3739   -2.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1615   -5.1663   -5.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658   -0.7154    0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4971    0.8914    1.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1431    3.4909    2.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
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 12 58  1  0
 12 59  1  0
 13 60  1  0
 15 61  1  0
 16 62  1  0
 20 63  1  0
 21 64  1  1
 22 65  1  0
 22 66  1  0
 23 67  1  0
 23 68  1  0
 26 69  1  0
 27 70  1  1
 28 71  1  0
 28 72  1  0
 29 73  1  0
 29 74  1  0
 32 75  1  0
 33 76  1  1
 34 77  1  0
 34 78  1  0
 35 79  1  0
 35 80  1  0
 38 81  1  0
 41 82  1  0
 44 83  1  0
 47 84  1  0
 48 85  1  0
 49 86  1  0
 50 87  1  0
M  END
Download

PDB for HMDB0012290 (Tetrahydropteroyltri-L-glutamic acid)

HEADER    PROTEIN                                 05-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAR-20         0                                  
HETATM    1  O   UNK     0    8651.2938667.452   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8651.2938665.912   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8652.6238665.136   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8652.6238663.585   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8653.9538662.809   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8655.2868663.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8655.2868665.136   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0    8653.9538665.912   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0    8656.6208665.904   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    8657.9548665.136   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0    8663.2888668.214   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0    8664.6228667.444   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0    8665.9558668.214   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.2888667.444   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.6248668.214   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.9568667.444   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0    8671.2898668.214   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0    8672.6258667.444   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8673.9578668.214   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8675.2938667.444   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8676.6298668.214   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0    8677.9618667.444   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0    8679.2978668.214   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8680.6298667.444   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8681.9658668.214   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8683.2978667.444   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8684.6298668.214   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0    8683.2978665.904   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0    8679.2978669.754   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0    8680.6298670.524   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0    8677.9618670.524   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0    8676.6298669.754   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8672.6258665.904   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0    8673.9578665.136   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0    8671.2898665.136   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0    8669.9568665.904   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0    8665.9558669.754   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0    8667.2888670.524   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0    8664.6228670.524   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0    8663.2888669.754   0.000  0.00  0.00           O+0
HETATM   41  N   UNK     0    8651.2938662.809   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0    8649.9638663.585   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0    8649.9638665.136   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0    8648.6308662.813   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0    8661.9558667.445   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0    8660.6218668.215   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0    8659.2878667.445   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0    8659.2878665.905   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0    8660.6218665.135   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0    8661.9558665.905   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1   43    3                                                  
CONECT    3    2    4    8                                                  
CONECT    4   41    3    5                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    9    6    8                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   48                                                       
CONECT   11   12   40   45                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   37                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   32                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   21                                                            
CONECT   33   18   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   16                                                            
CONECT   37   13   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   11                                                            
CONECT   41    4   42                                                       
CONECT   42   44   43   41                                                  
CONECT   43   42    2                                                       
CONECT   44   42                                                            
CONECT   45   46   50   11                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   10                                                  
CONECT   49   48   50                                                       
CONECT   50   49   45                                                       
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END
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3D PDB for HMDB0012290 (Tetrahydropteroyltri-L-glutamic acid)

COMPND    HMDB0012290
HETATM    1  N1  UNL     1      10.276   4.936  -1.551  1.00  0.00           N  
HETATM    2  C1  UNL     1       9.423   4.417  -0.541  1.00  0.00           C  
HETATM    3  N2  UNL     1       8.358   5.132  -0.126  1.00  0.00           N  
HETATM    4  C2  UNL     1       7.531   4.673   0.824  1.00  0.00           C  
HETATM    5  O1  UNL     1       6.527   5.319   1.233  1.00  0.00           O  
HETATM    6  C3  UNL     1       7.751   3.444   1.409  1.00  0.00           C  
HETATM    7  C4  UNL     1       8.854   2.734   0.961  1.00  0.00           C  
HETATM    8  N3  UNL     1       9.677   3.204   0.006  1.00  0.00           N  
HETATM    9  N4  UNL     1       9.100   1.452   1.562  1.00  0.00           N  
HETATM   10  C5  UNL     1       8.635   1.286   2.919  1.00  0.00           C  
HETATM   11  C6  UNL     1       7.151   1.568   2.901  1.00  0.00           C  
HETATM   12  C7  UNL     1       6.515   0.497   2.031  1.00  0.00           C  
HETATM   13  N5  UNL     1       5.078   0.701   1.951  1.00  0.00           N  
HETATM   14  C8  UNL     1       4.261  -0.219   1.250  1.00  0.00           C  
HETATM   15  C9  UNL     1       4.833  -1.343   0.694  1.00  0.00           C  
HETATM   16  C10 UNL     1       4.023  -2.250   0.016  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.654  -2.047  -0.114  1.00  0.00           C  
HETATM   18  C12 UNL     1       1.876  -3.045  -0.804  1.00  0.00           C  
HETATM   19  O2  UNL     1       2.340  -4.226  -0.788  1.00  0.00           O  
HETATM   20  N6  UNL     1       0.643  -2.765  -1.483  1.00  0.00           N  
HETATM   21  C13 UNL     1      -0.034  -3.868  -2.127  1.00  0.00           C  
HETATM   22  C14 UNL     1      -1.486  -3.972  -1.845  1.00  0.00           C  
HETATM   23  C15 UNL     1      -2.317  -2.794  -2.299  1.00  0.00           C  
HETATM   24  C16 UNL     1      -3.709  -3.071  -1.913  1.00  0.00           C  
HETATM   25  O3  UNL     1      -3.970  -3.948  -1.051  1.00  0.00           O  
HETATM   26  N7  UNL     1      -4.775  -2.362  -2.508  1.00  0.00           N  
HETATM   27  C17 UNL     1      -6.135  -2.692  -2.067  1.00  0.00           C  
HETATM   28  C18 UNL     1      -7.064  -1.600  -2.389  1.00  0.00           C  
HETATM   29  C19 UNL     1      -6.765  -0.264  -1.793  1.00  0.00           C  
HETATM   30  C20 UNL     1      -6.773  -0.330  -0.319  1.00  0.00           C  
HETATM   31  O4  UNL     1      -6.882  -1.409   0.275  1.00  0.00           O  
HETATM   32  N8  UNL     1      -6.649   0.932   0.377  1.00  0.00           N  
HETATM   33  C21 UNL     1      -6.635   0.972   1.836  1.00  0.00           C  
HETATM   34  C22 UNL     1      -5.771   2.029   2.418  1.00  0.00           C  
HETATM   35  C23 UNL     1      -6.210   3.398   2.024  1.00  0.00           C  
HETATM   36  C24 UNL     1      -5.337   4.463   2.612  1.00  0.00           C  
HETATM   37  O5  UNL     1      -4.362   4.210   3.350  1.00  0.00           O  
HETATM   38  O6  UNL     1      -5.607   5.813   2.336  1.00  0.00           O  
HETATM   39  C25 UNL     1      -8.087   1.192   2.217  1.00  0.00           C  
HETATM   40  O7  UNL     1      -9.007   1.298   1.379  1.00  0.00           O  
HETATM   41  O8  UNL     1      -8.376   1.275   3.558  1.00  0.00           O  
HETATM   42  C26 UNL     1      -6.588  -3.887  -2.897  1.00  0.00           C  
HETATM   43  O9  UNL     1      -5.834  -4.382  -3.748  1.00  0.00           O  
HETATM   44  O10 UNL     1      -7.839  -4.401  -2.685  1.00  0.00           O  
HETATM   45  C27 UNL     1       0.164  -3.775  -3.631  1.00  0.00           C  
HETATM   46  O11 UNL     1       0.816  -2.837  -4.126  1.00  0.00           O  
HETATM   47  O12 UNL     1      -0.429  -4.796  -4.369  1.00  0.00           O  
HETATM   48  C28 UNL     1       2.118  -0.914   0.453  1.00  0.00           C  
HETATM   49  C29 UNL     1       2.913   0.012   1.141  1.00  0.00           C  
HETATM   50  N9  UNL     1       6.926   2.896   2.404  1.00  0.00           N  
HETATM   51  H1  UNL     1      11.231   5.206  -1.261  1.00  0.00           H  
HETATM   52  H2  UNL     1       9.943   5.034  -2.522  1.00  0.00           H  
HETATM   53  H3  UNL     1      10.506   2.613  -0.297  1.00  0.00           H  
HETATM   54  H4  UNL     1       9.583   0.712   1.029  1.00  0.00           H  
HETATM   55  H5  UNL     1       8.746   0.212   3.246  1.00  0.00           H  
HETATM   56  H6  UNL     1       9.166   1.969   3.614  1.00  0.00           H  
HETATM   57  H7  UNL     1       6.739   1.522   3.944  1.00  0.00           H  
HETATM   58  H8  UNL     1       6.759  -0.513   2.373  1.00  0.00           H  
HETATM   59  H9  UNL     1       6.975   0.620   1.006  1.00  0.00           H  
HETATM   60  H10 UNL     1       4.657   1.531   2.414  1.00  0.00           H  
HETATM   61  H11 UNL     1       5.912  -1.497   0.798  1.00  0.00           H  
HETATM   62  H12 UNL     1       4.491  -3.131  -0.412  1.00  0.00           H  
HETATM   63  H13 UNL     1       0.300  -1.787  -1.475  1.00  0.00           H  
HETATM   64  H14 UNL     1       0.465  -4.819  -1.862  1.00  0.00           H  
HETATM   65  H15 UNL     1      -1.885  -4.872  -2.356  1.00  0.00           H  
HETATM   66  H16 UNL     1      -1.653  -4.092  -0.751  1.00  0.00           H  
HETATM   67  H17 UNL     1      -2.213  -2.566  -3.377  1.00  0.00           H  
HETATM   68  H18 UNL     1      -1.896  -1.911  -1.748  1.00  0.00           H  
HETATM   69  H19 UNL     1      -4.692  -1.624  -3.236  1.00  0.00           H  
HETATM   70  H20 UNL     1      -6.067  -3.066  -1.049  1.00  0.00           H  
HETATM   71  H21 UNL     1      -7.092  -1.440  -3.508  1.00  0.00           H  
HETATM   72  H22 UNL     1      -8.140  -1.873  -2.165  1.00  0.00           H  
HETATM   73  H23 UNL     1      -5.780   0.078  -2.191  1.00  0.00           H  
HETATM   74  H24 UNL     1      -7.499   0.506  -2.137  1.00  0.00           H  
HETATM   75  H25 UNL     1      -6.567   1.823  -0.126  1.00  0.00           H  
HETATM   76  H26 UNL     1      -6.336  -0.039   2.181  1.00  0.00           H  
HETATM   77  H27 UNL     1      -4.702   1.883   2.112  1.00  0.00           H  
HETATM   78  H28 UNL     1      -5.760   1.894   3.516  1.00  0.00           H  
HETATM   79  H29 UNL     1      -7.229   3.580   2.447  1.00  0.00           H  
HETATM   80  H30 UNL     1      -6.272   3.507   0.935  1.00  0.00           H  
HETATM   81  H31 UNL     1      -6.091   6.031   1.476  1.00  0.00           H  
HETATM   82  H32 UNL     1      -9.196   0.722   3.858  1.00  0.00           H  
HETATM   83  H33 UNL     1      -8.072  -5.374  -2.541  1.00  0.00           H  
HETATM   84  H34 UNL     1       0.162  -5.166  -5.133  1.00  0.00           H  
HETATM   85  H35 UNL     1       1.066  -0.715   0.380  1.00  0.00           H  
HETATM   86  H36 UNL     1       2.497   0.891   1.587  1.00  0.00           H  
HETATM   87  H37 UNL     1       6.143   3.491   2.762  1.00  0.00           H  
CONECT    1    2   51   52
CONECT    2    3    3    8
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7    7   50
CONECT    7    8    9
CONECT    8   53
CONECT    9   10   54
CONECT   10   11   55   56
CONECT   11   12   50   57
CONECT   12   13   58   59
CONECT   13   14   60
CONECT   14   15   15   49
CONECT   15   16   61
CONECT   16   17   17   62
CONECT   17   18   48
CONECT   18   19   19   20
CONECT   20   21   63
CONECT   21   22   45   64
CONECT   22   23   65   66
CONECT   23   24   67   68
CONECT   24   25   25   26
CONECT   26   27   69
CONECT   27   28   42   70
CONECT   28   29   71   72
CONECT   29   30   73   74
CONECT   30   31   31   32
CONECT   32   33   75
CONECT   33   34   39   76
CONECT   34   35   77   78
CONECT   35   36   79   80
CONECT   36   37   37   38
CONECT   38   81
CONECT   39   40   40   41
CONECT   41   82
CONECT   42   43   43   44
CONECT   44   83
CONECT   45   46   46   47
CONECT   47   84
CONECT   48   49   49   85
CONECT   49   86
CONECT   50   87
END
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SMILES for HMDB0012290 (Tetrahydropteroyltri-L-glutamic acid)

NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N1
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INCHI for HMDB0012290 (Tetrahydropteroyltri-L-glutamic acid)

InChI=1S/C29H37N9O12/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/h1-4,15-18,31,33H,5-12H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H4,30,32,37,38,44)/t15-,16-,17-,18-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Tetrahydropteroyltri-L-glutamateChEBI
(6S)-H4PteGlu3Kegg
Tetrahydropteroyltri-L-glutamic acidGenerator
Tetrahydropteroyltri-gamma-glutamic acidHMDB
Tetrahydropteroyltri-γ-glutamic acidHMDB
Tetrahydropteroyl tri-L-glutamateHMDB
Tetrahydropteroyl tri-L-glutamic acidHMDB
Chemical FormulaC29H37N9O12
Average Molecular Weight703.6572
Monoisotopic Molecular Weight703.256167693
IUPAC Name(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid
Traditional Name(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid
CAS Registry Number88903-89-3
SMILES
NC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N1
InChI Identifier
InChI=1S/C29H37N9O12/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/h1-4,15-18,31,33H,5-12H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H4,30,32,37,38,44)/t15-,16-,17-,18-/m0/s1
InChI KeyRXWVHRYZTWZATH-XSLAGTTESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentTetrahydrofolic acids and derivatives
Alternative Parents
Substituents
  • Tetrahydrofolic acid or derivatives
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamic acid or derivatives
  • Glutamine or derivatives
  • Tetracarboxylic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Aminobenzamide
  • Alpha-amino acid or derivatives
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Phenylalkylamine
  • Benzoyl
  • Aniline or substituted anilines
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • N-acyl-amine
  • Pyrimidine
  • Fatty acyl
  • Monocyclic benzene moiety
  • Fatty amide
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Secondary amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP-1.6ALOGPS
logP-4.3ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.59ChemAxon
pKa (Strongest Basic)3.12ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area340.07 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity177.56 m³·mol⁻¹ChemAxon
Polarizability69.1 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
DeepCCS[M+H]+241.81230932474
DeepCCS[M-H]-239.98730932474
DeepCCS[M-2H]-273.88330932474
DeepCCS[M+Na]+247.70330932474
AllCCS[M+H]+240.732859911
AllCCS[M+H-H2O]+240.632859911
AllCCS[M+NH4]+240.832859911
AllCCS[M+Na]+240.832859911
AllCCS[M-H]-238.632859911
AllCCS[M+Na-2H]-241.832859911
AllCCS[M+HCOO]-245.332859911

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, 2022.2.32 minutes32390414
Predicted by Siyang on May 30, 202211.5737 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20228.83 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid564.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid567.9 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid214.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid82.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid183.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid78.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid319.4 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 Acid385.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)1260.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid705.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid165.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid946.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid255.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid357.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate638.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA588.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water637.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tetrahydropteroyltri-L-glutamic acidNC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N17167.2Standard polar33892256
Tetrahydropteroyltri-L-glutamic acidNC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N15532.8Standard non polar33892256
Tetrahydropteroyltri-L-glutamic acidNC1=NC(=O)C2=C(NC[C@H](CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)N2)N17385.0Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
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 IDFDB028919
KNApSAcK IDNot Available
Chemspider ID17625690
KEGG Compound IDC04144
BioCyc IDCPD-1301
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16722112
PDB ID39S
ChEBI ID17420
Food Biomarker OntologyNot Available
VMH IDM02979
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Methionine synthase
General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91
Reactions
Selenohomocysteine + 5-Methyltetrahydropteroyltri-L-glutamic acid → Selenomethionine + Tetrahydropteroyltri-L-glutamic aciddetails