Showing metabocard for Glutamic acid gamma-methyl ester (MMDBc0000817)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 22:03:41 UTC
Update Date2024-04-30 19:33:45 UTC
Metabolite IDMMDBc0000817
Metabolite Identification
Common NameGlutamic acid gamma-methyl ester
DescriptionGlutamate gamma-methyl ester, also known as L-Glutamic acid 5-methyl ester or g-methyl-L-glutamate (CAS# 1499-55-4) is a white amorphous powder and soluble in water. Its melting point is 182 degree Celsius and should be stored at 2-8 degree Celsius Glutamic acid gamma-methyl ester has been identified in the human placenta (PMID: 32033212 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd12ea60bb0>


  Mrv1652305062021442D          

 11 10  0  0  0  0            999 V2000
10013.719610013.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.003610013.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.289210013.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.574810013.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.858310013.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.289210012.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10014.435110013.5622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10015.148410013.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.863910013.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.148410012.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10014.435110014.3869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fd12ea60bb0>

HMDB0061715
     RDKit          3D
Glutamic acid gamma-methyl ester
 22 21  0  0  0  0  0  0  0  0999 V2000
   -3.5242    1.1149    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048    0.4498    0.7593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155   -0.0922    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3908    0.0436   -1.1436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -0.7997    0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646   -1.2488   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -0.1552   -0.8672 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4778   -0.8011   -1.7092 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698    0.7342    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    0.7940    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    1.5313    0.9985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222    1.9624    0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0988    1.4962   -0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470    0.4234   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -1.7111    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0812   -0.1693    1.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290   -1.9620   -0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -1.8261    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184    0.4484   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -1.6157   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1029   -1.0380   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302    2.4208    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  6
  8 20  1  0
  8 21  1  0
 11 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fd12ea60bb0>


  Mrv1652305062021442D          

 11 10  0  0  0  0            999 V2000
10013.719610013.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.003610013.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.289210013.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.574810013.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.858310013.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.289210012.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10014.435110013.5622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10015.148410013.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.863910013.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10015.148410012.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10014.435110014.3869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000817

> <DATABASE_NAME>
MIME

> <SMILES>
COC(=O)CC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO4/c1-11-5(8)3-2-4(7)6(9)10/h4H,2-3,7H2,1H3,(H,9,10)/t4-/m0/s1

> <INCHI_KEY>
ZGEYCCHDTIDZAE-BYPYZUCNSA-N

> <FORMULA>
C6H11NO4

> <MOLECULAR_WEIGHT>
161.1558

> <EXACT_MASS>
161.068807845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.51098772284789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-5-methoxy-5-oxopentanoic acid

> <ALOGPS_LOGP>
-2.86

> <JCHEM_LOGP>
-3.0484793149869387

> <ALOGPS_LOGS>
-0.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0167130287203867

> <JCHEM_PKA_STRONGEST_BASIC>
9.51087867661671

> <JCHEM_POLAR_SURFACE_AREA>
89.62

> <JCHEM_REFRACTIVITY>
36.0568

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-5-methoxy-5-oxopentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fd12ea60bb0>

HMDB0061715
     RDKit          3D
Glutamic acid gamma-methyl ester
 22 21  0  0  0  0  0  0  0  0999 V2000
   -3.5242    1.1149    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048    0.4498    0.7593 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155   -0.0922    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3908    0.0436   -1.1436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -0.7997    0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7646   -1.2488   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -0.1552   -0.8672 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4778   -0.8011   -1.7092 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1698    0.7342    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    0.7940    0.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    1.5313    0.9985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222    1.9624    0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0988    1.4962   -0.8816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3470    0.4234   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -1.7111    1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0812   -0.1693    1.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290   -1.9620   -0.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -1.8261    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8184    0.4484   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353   -1.6157   -1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1029   -1.0380   -2.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302    2.4208    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  6
  8 20  1  0
  8 21  1  0
 11 22  1  0
M  END
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PDB for #<Metabolite:0x00007fd12ea60bb0>

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  C   UNK     0    8692.2778691.214   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8690.9408691.983   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8689.6078691.214   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8688.2738691.983   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8686.9358691.210   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8689.6078689.674   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8693.6128691.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8694.9448691.214   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8696.2798691.983   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8694.9448689.674   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0    8693.6128693.522   0.000  0.00  0.00           N+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007fd12ea60bb0>

COMPND    HMDB0061715
HETATM    1  C1  UNL     1      -3.524   1.115   0.074  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.505   0.450   0.759  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.416  -0.092   0.097  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.391   0.044  -1.144  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.325  -0.800   0.797  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.765  -1.249  -0.132  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.461  -0.155  -0.867  1.00  0.00           C  
HETATM    8  N1  UNL     1       2.478  -0.801  -1.709  1.00  0.00           N  
HETATM    9  C6  UNL     1       2.170   0.734   0.077  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.423   0.794   0.069  1.00  0.00           O  
HETATM   11  O4  UNL     1       1.520   1.531   0.999  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.922   1.962   0.670  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.099   1.496  -0.882  1.00  0.00           H  
HETATM   14  H3  UNL     1      -4.347   0.423  -0.134  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.794  -1.711   1.244  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.081  -0.169   1.636  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.329  -1.962  -0.878  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.510  -1.826   0.478  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.818   0.448  -1.534  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.835  -1.616  -1.180  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.103  -1.038  -2.633  1.00  0.00           H  
HETATM   22  H11 UNL     1       1.830   2.421   1.314  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8    9   19
CONECT    8   20   21
CONECT    9   10   10   11
CONECT   11   22
END
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SMILES for #<Metabolite:0x00007fd12ea60bb0>

COC(=O)CC[C@H](N)C(O)=O
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INCHI for #<Metabolite:0x00007fd12ea60bb0>

InChI=1S/C6H11NO4/c1-11-5(8)3-2-4(7)6(9)10/h4H,2-3,7H2,1H3,(H,9,10)/t4-/m0/s1
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Synonyms
ValueSource
L-Glutamate 5-methyl esterGenerator
PGMGTMeSH
Poly-gamma-methylglutamic acidMeSH
Poly(gamma-methyl L-glutamate)MeSH
Poly-gamma-methylglutamateMeSH
PMLG PolymerMeSH
Poly(gamma-methyl-L-glutamate)MeSH
(2S)-2-Amino-5-methoxy-5-oxopentanoateGenerator
(2S)-2-Amino-5-methoxy-5-oxo-pentanoic acidHMDB
(S)-2-Aminopentanedioic acid 5-methyl esterHMDB
(S)-Glutamic acid 5-methyl esterHMDB
4(S)-Carboxy-4-aminobutanoic acid methyl esterHMDB
5-Methyl L-glutamateHMDB
Glutamate gamma-methyl esterHMDB
Glutamate γ-methyl esterHMDB
Glutamic acid 5-methyl esterHMDB
L-Glutamic acid gamma-methyl esterHMDB
L-Glutamic acid γ-methyl esterHMDB
gamma-Methyl (S)-glutamateHMDB
gamma-Methyl L-glutamateHMDB
γ-Methyl (S)-glutamateHMDB
γ-Methyl L-glutamateHMDB
Molecular FormulaC6H11NO4
Average Mass161.1558
Monoisotopic Mass161.068807845
IUPAC Name(2S)-2-amino-5-methoxy-5-oxopentanoic acid
Traditional Name(2S)-2-amino-5-methoxy-5-oxopentanoic acid
CAS Registry NumberNot Available
SMILES
COC(=O)CC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H11NO4/c1-11-5(8)3-2-4(7)6(9)10/h4H,2-3,7H2,1H3,(H,9,10)/t4-/m0/s1
InChI KeyZGEYCCHDTIDZAE-BYPYZUCNSA-N