MiMeDB: Showing metabocard for N5-methyl--tetrahydropteroyl tri-L-glutamate (MMDBc0032122)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:03:18 UTC

Update Date

2022-08-31 18:30:43 UTC

Metabolite ID

MMDBc0032122

Metabolite Identification

Common Name

N5-methyl--tetrahydropteroyl tri-L-glutamate

Description

N5-methyl--tetrahydropteroyl tri-L-glutamate is an intermediate in pathways L-methionine biosynthesis I and S-adenosyl-L-methionine cycle I in E.coli. It is a substrate for enzyme cobalamin-independent homocysteine transmethylase in both pathways and a substrate for enzyme cobalamin-dependent methionine synthase in pathway L-methionine biosynthesis I (BioCyc compound: CPD-1302).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04091516592D          

 55 57  0  0  1  0            999 V2000
   -7.1960    4.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710   -0.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085    0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960    1.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085   -6.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960   -2.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9085   -7.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4335   -6.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085   -3.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3210   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710    2.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1335    3.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960   -0.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710    1.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    3.4835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1960   -5.8046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0835   -7.9480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6085   -2.2322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8460   -7.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960   -4.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    4.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1335    4.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085   -0.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710    5.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710   -5.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6710   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4335   -2.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1335    6.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7210    7.0558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    2.0545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7210    4.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085   -5.0901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6710   -7.2335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960   -1.5177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7210    5.6269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    6.3413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710    4.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4335   -7.9480    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -6.3710   -4.3756    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -12.5585   -9.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5585   -7.9480    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -8.4335   -0.8033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960    5.6269    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.9585   -5.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585   -6.5190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8460   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0835   -9.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8460   -1.5177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8460   -2.9467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835    3.4835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835   -6.5190    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4960   -8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0210   -2.9467    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 14  2  2  0  0  0  0
 14  3  1  0  0  0  0
 15  4  2  0  0  0  0
 15  5  1  0  0  0  0
 16 12  1  6  0  0  0
 16 13  1  0  0  0  0
 17  6  1  0  0  0  0
 18  8  1  0  0  0  0
 19  7  1  0  0  0  0
 20  9  1  0  0  0  0
 21 10  1  0  0  0  0
 22 11  1  0  0  0  0
 24 23  2  0  0  0  0
 25 14  1  0  0  0  0
 26 23  1  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 31 30  2  0  0  0  0
 32 12  1  0  0  0  0
 32 15  1  0  0  0  0
 33 13  1  0  0  0  0
 33 24  1  0  0  0  0
 17 34  1  1  0  0  0
 34 21  2  0  0  0  0
 18 35  1  1  0  0  0
 35 20  2  0  0  0  0
 19 36  1  6  0  0  0
 36 25  1  0  0  0  0
 37 24  1  0  0  0  0
 37 30  1  0  0  0  0
 38 26  2  0  0  0  0
 38 30  1  0  0  0  0
 39  1  1  0  0  0  0
 39 16  1  0  0  0  0
 39 23  1  0  0  0  0
 20 40  1  4  0  0  0
 21 41  1  4  0  0  0
 42 22  2  0  0  0  0
 43 22  1  0  0  0  0
 44 25  2  0  0  0  0
 45 26  1  0  0  0  0
 46 27  2  0  0  0  0
 47 27  1  0  0  0  0
 48 28  2  0  0  0  0
 49 28  1  0  0  0  0
 50 29  2  0  0  0  0
 51 29  1  0  0  0  0
 16 52  1  1  0  0  0
 17 53  1  1  0  0  0
 18 54  1  1  0  0  0
 19 55  1  6  0  0  0
M  CHG  4  40  -1  41  -1  43  -1  45  -1
M  END


  Mrv0541 04091516592D          

 55 57  0  0  1  0            999 V2000
   -7.1960    4.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710   -0.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085    0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    0.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960    1.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085   -6.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960   -2.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9085   -7.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4335   -6.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085   -3.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3210   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710    2.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1335    3.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960   -0.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710    1.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    3.4835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.1960   -5.8046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -10.0835   -7.9480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6085   -2.2322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8460   -7.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960   -4.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1460   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    4.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1335    4.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085   -0.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710    5.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710   -5.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6710   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4335   -2.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1335    6.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7210    7.0558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    2.0545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7210    4.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6085   -5.0901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6710   -7.2335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960   -1.5177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7210    5.6269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585    6.3413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3710    4.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4335   -7.9480    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -6.3710   -4.3756    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -12.5585   -9.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5585   -7.9480    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -8.4335   -0.8033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1960    5.6269    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.9585   -5.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9585   -6.5190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8460   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0835   -9.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8460   -1.5177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8460   -2.9467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835    3.4835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7835   -6.5190    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4960   -8.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0210   -2.9467    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 14  2  2  0  0  0  0
 14  3  1  0  0  0  0
 15  4  2  0  0  0  0
 15  5  1  0  0  0  0
 16 12  1  6  0  0  0
 16 13  1  0  0  0  0
 17  6  1  0  0  0  0
 18  8  1  0  0  0  0
 19  7  1  0  0  0  0
 20  9  1  0  0  0  0
 21 10  1  0  0  0  0
 22 11  1  0  0  0  0
 24 23  2  0  0  0  0
 25 14  1  0  0  0  0
 26 23  1  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 31 30  2  0  0  0  0
 32 12  1  0  0  0  0
 32 15  1  0  0  0  0
 33 13  1  0  0  0  0
 33 24  1  0  0  0  0
 17 34  1  1  0  0  0
 34 21  2  0  0  0  0
 18 35  1  1  0  0  0
 35 20  2  0  0  0  0
 19 36  1  6  0  0  0
 36 25  1  0  0  0  0
 37 24  1  0  0  0  0
 37 30  1  0  0  0  0
 38 26  2  0  0  0  0
 38 30  1  0  0  0  0
 39  1  1  0  0  0  0
 39 16  1  0  0  0  0
 39 23  1  0  0  0  0
 20 40  1  4  0  0  0
 21 41  1  4  0  0  0
 42 22  2  0  0  0  0
 43 22  1  0  0  0  0
 44 25  2  0  0  0  0
 45 26  1  0  0  0  0
 46 27  2  0  0  0  0
 47 27  1  0  0  0  0
 48 28  2  0  0  0  0
 49 28  1  0  0  0  0
 50 29  2  0  0  0  0
 51 29  1  0  0  0  0
 16 52  1  1  0  0  0
 17 53  1  1  0  0  0
 18 54  1  1  0  0  0
 19 55  1  6  0  0  0
M  CHG  4  40  -1  41  -1  43  -1  45  -1
M  END
> <DATABASE_ID>
MMDBc0032122

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CCC([O-])=N[C@@]([H])(CCC([O-])=N[C@@]([H])(CCC([O-])=O)C(O)=O)C(O)=O)(NC(=O)C1=CC=C(NC[C@@]2([H])CNC3=C(N2C)C([O-])=NC(=N)N3)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H39N9O12/c1-39-16(13-33-24-23(39)26(45)38-30(31)37-24)12-32-15-4-2-14(3-5-15)25(44)36-19(29(50)51)7-10-21(41)34-17(27(46)47)6-9-20(40)35-18(28(48)49)8-11-22(42)43/h2-5,16-19,32H,6-13H2,1H3,(H,34,41)(H,35,40)(H,36,44)(H,42,43)(H,46,47)(H,48,49)(H,50,51)(H4,31,33,37,38,45)/p-4/t16-,17-,18-,19-/m0/s1

> <INCHI_KEY>
HVRNKDVLFAVCJF-VJANTYMQSA-J

> <FORMULA>
C30H35N9O12

> <MOLECULAR_WEIGHT>
713.663

> <EXACT_MASS>
713.242711923

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
69.36215538757513

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[4-({[(6S)-2-imino-5-methyl-4-oxido-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-1-oxidobutylidene]amino}-1-oxidobutylidene]amino}butanoate

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-2.674465492198029

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.80687895417836

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3316775730395864

> <JCHEM_PKA_STRONGEST_BASIC>
15.00000002123984

> <JCHEM_POLAR_SURFACE_AREA>
350.57

> <JCHEM_REFRACTIVITY>
237.40280000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[4-({[(6S)-2-imino-5-methyl-4-oxido-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}-1-oxidobutylidene]amino}-1-oxidobutylidene]amino}butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-15         0                                  
HETATM    1  C   UNK     0     -13.433   7.836   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.893  -0.166   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.203   1.168   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.123   1.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -13.433   2.501   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -14.203 -12.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -13.433  -5.501   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -20.363 -14.836   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -15.743 -12.169   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.203  -6.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -21.133 -16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -11.893   5.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.583   6.503   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.433  -0.166   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -11.893   2.501   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -11.123   6.503   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -13.433 -10.835   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -18.823 -14.836   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -14.203  -4.167   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -16.513 -13.503   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -13.433  -8.168   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -11.123   9.170   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.583   9.170   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.203  -1.499   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -11.893  10.504   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -11.893 -10.835   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -18.053 -16.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -15.743  -4.167   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -9.583  11.837   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -8.813  13.171   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0     -11.123   3.835   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0      -8.813   7.836   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0     -14.203  -9.502   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0     -18.053 -13.503   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0     -13.433  -2.833   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0      -8.813  10.504   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0     -11.123  11.837   0.000  0.00  0.00           N+0
HETATM   39  N   UNK     0     -11.893   7.836   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0     -15.743 -14.836   0.000  0.00  0.00           O-1
HETATM   41  O   UNK     0     -11.893  -8.168   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0     -23.443 -17.504   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -23.443 -14.836   0.000  0.00  0.00           O-1
HETATM   44  O   UNK     0     -15.743  -1.499   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0     -13.433  10.504   0.000  0.00  0.00           O-1
HETATM   46  O   UNK     0     -11.123  -9.502   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0     -11.123 -12.169   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -16.513 -16.170   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -18.823 -17.504   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0     -16.513  -2.833   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0     -16.513  -5.501   0.000  0.00  0.00           O+0
HETATM   52  H   UNK     0     -12.663   6.503   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0     -12.663 -12.169   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0     -19.593 -16.170   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0     -14.973  -5.501   0.000  0.00  0.00           H+0
CONECT    1   39                                                            
CONECT    2    4   14                                                       
CONECT    3    5   14                                                       
CONECT    4    2   15                                                       
CONECT    5    3   15                                                       
CONECT    6    9   17                                                       
CONECT    7   10   19                                                       
CONECT    8   11   18                                                       
CONECT    9    6   20                                                       
CONECT   10    7   21                                                       
CONECT   11    8   22                                                       
CONECT   12   16   32                                                       
CONECT   13   16   33                                                       
CONECT   14    2    3   25                                                  
CONECT   15    4    5   32                                                  
CONECT   16   12   13   39   52                                             
CONECT   17    6   27   34   53                                             
CONECT   18    8   28   35   54                                             
CONECT   19    7   29   36   55                                             
CONECT   20    9   35   40                                                  
CONECT   21   10   34   41                                                  
CONECT   22   11   42   43                                                  
CONECT   23   24   26   39                                                  
CONECT   24   23   33   37                                                  
CONECT   25   14   36   44                                                  
CONECT   26   23   38   45                                                  
CONECT   27   17   46   47                                                  
CONECT   28   18   48   49                                                  
CONECT   29   19   50   51                                                  
CONECT   30   31   37   38                                                  
CONECT   31   30                                                            
CONECT   32   12   15                                                       
CONECT   33   13   24                                                       
CONECT   34   17   21                                                       
CONECT   35   18   20                                                       
CONECT   36   19   25                                                       
CONECT   37   24   30                                                       
CONECT   38   26   30                                                       
CONECT   39    1   16   23                                                  
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   22                                                            
CONECT   44   25                                                            
CONECT   45   26                                                            
CONECT   46   27                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
CONECT   49   28                                                            
CONECT   50   29                                                            
CONECT   51   29                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

Synonyms

Value	Source
5-Methyltetrahydropteroyltri-L-glutamate	ChEBI
5-Methyltetrahydropteroyltri-L-glutamate tetraanion	ChEBI
5-Methyltetrahydropteroyltri-L-glutamic acid	Generator
5-Methyltetrahydropteroyltri-L-glutamic acid tetraanion	Generator
N5-Methyl--tetrahydropteroyl tri-L-glutamic acid	Generator

Molecular Formula

C₃₀H₃₅N₉O₁₂

Average Mass

713.663

Monoisotopic Mass

713.242711923

IUPAC Name

(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[4-({[(6S)-2-imino-5-methyl-4-oxido-1,2,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-1-oxidobutylidene]amino}-1-oxidobutylidene]amino}butanoate

Traditional Name

(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[4-({[(6S)-2-imino-5-methyl-4-oxido-1,6,7,8-tetrahydropteridin-6-yl]methyl}amino)phenyl]formamido}-1-oxidobutylidene]amino}-1-oxidobutylidene]amino}butanoate

CAS Registry Number

Not Available

SMILES

[H][C@@](CCC([O-])=N[C@@]([H])(CCC([O-])=N[C@@]([H])(CCC([O-])=O)C(O)=O)C(O)=O)(NC(=O)C1=CC=C(NC[C@@]2([H])CNC3=C(N2C)C([O-])=NC(=N)N3)C=C1)C(O)=O

InChI Identifier

InChI=1S/C30H39N9O12/c1-39-16(13-33-24-23(39)26(45)38-30(31)37-24)12-32-15-4-2-14(3-5-15)25(44)36-19(29(50)51)7-10-21(41)34-17(27(46)47)6-9-20(40)35-18(28(48)49)8-11-22(42)43/h2-5,16-19,32H,6-13H2,1H3,(H,34,41)(H,35,40)(H,36,44)(H,42,43)(H,46,47)(H,48,49)(H,50,51)(H4,31,33,37,38,45)/p-4/t16-,17-,18-,19-/m0/s1

InChI Key

HVRNKDVLFAVCJF-VJANTYMQSA-J

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).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Tetrahydrofolic 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
N-acyl-l-alpha-amino acid
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Benzamide
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Pyrimidine
Monocyclic benzene moiety
Benzenoid
N-acyl-amine
Fatty acyl
Fatty amide
Vinylogous amide
Heteroaromatic compound
Tertiary amine
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Carboxamide group
Secondary amine
Carboxylic acid derivative
Carboxylic acid
Azacycle
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Primary amine
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

peptide anion (CHEBI:58207 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	0.17	ALOGPS
logP	-2.7	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.33	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	350.57 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	237.4 m³·mol⁻¹	ChemAxon
Polarizability	69.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-0000000900-622abdc32cc315dd322c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056s-0000006900-3ddf859d7290a4a4d352	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-1110016900-06be6f05afb65b6aac2f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000900-49d9a35d9762d5451de9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2000001900-3cde656cf075950f0b36	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000001100-f03d9d7c285194175ee5	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49852302

PDB ID

Not Available

ChEBI ID

58207

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for N5-methyl--tetrahydropteroyl tri-L-glutamate (MMDBc0032122)

MOL for #<Metabolite:0x00007f46d8769be0>

3D MOL for #<Metabolite:0x00007f46d8769be0>

3D SDF for #<Metabolite:0x00007f46d8769be0>

3D-SDF for #<Metabolite:0x00007f46d8769be0>

PDB for #<Metabolite:0x00007f46d8769be0>

3D PDB for #<Metabolite:0x00007f46d8769be0>

SMILES for #<Metabolite:0x00007f46d8769be0>

INCHI for #<Metabolite:0x00007f46d8769be0>

Structure for #<Metabolite:0x00007f46d8769be0>

3D Structure for #<Metabolite:0x00007f46d8769be0>