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Showing metabocard for Methylglutamic acid (HMDB0303007)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-23 22:32:43 UTC
Update Date2022-09-22 18:34:37 UTC
HMDB IDHMDB0303007
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethylglutamic acid
DescriptionMethylglutamic acid, also known as methylglutamate, is a member of the class of compounds known as methyl-branched fatty acids. Methyl-branched fatty acids are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Methylglutamic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Methylglutamic acid can be found in tamarind, which makes methylglutamic acid a potential biomarker for the consumption of this food product. N-Methyl-L-glutamic acid (methylglutamate) is a chemical derivative of glutamic acid in which a methyl group has been added to the amino group. It is an intermediate in methane metabolism. Biosynthetically, it is produced from methylamine and glutamic acid by the enzyme methylamine-glutamate N-methyltransferase. It can also be demethylated by methylglutamate dehydrogenase to regenerate glutamic acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0303007 (Methylglutamic acid)


  Mrv1533007131513482D          

 10  9  0  0  0  0            999 V2000
    4.6184    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
M  CHG  2   8  -1  10  -1
M  END
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3D MOL for HMDB0303007 (Methylglutamic acid)

HMDB0303007
     RDKit          3D
Methylglutamic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.1933   -0.9712    0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6312    0.4205    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    0.3523   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4011   -0.5597   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -0.1827    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.9417    0.4896 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836    0.9441    1.1026 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.7993    1.2685    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8779    0.6957   -0.2083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7897    2.6492    0.0541 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0062   -0.7877    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063   -1.3031   -0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -1.6478    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138    0.8289    1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4742    1.3814   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445   -0.0298   -1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460   -0.5064   -1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311   -1.6104   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
M  CHG  2   7  -1  10  -1
M  END
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3D SDF for HMDB0303007 (Methylglutamic acid)


  Mrv1533007131513482D          

 10  9  0  0  0  0            999 V2000
    4.6184    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
M  CHG  2   8  -1  10  -1
M  END
> <DATABASE_ID>
HMDB0303007

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCC([O-])=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)/p-2

> <INCHI_KEY>
AQYCMVICBNBXNA-UHFFFAOYSA-L

> <FORMULA>
C6H8O4

> <MOLECULAR_WEIGHT>
144.127

> <EXACT_MASS>
144.043355897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.12952724965238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpentanedioate

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
0.5890719759999997

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.676174036855368

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8942615644961287

> <JCHEM_POLAR_SURFACE_AREA>
80.25999999999999

> <JCHEM_REFRACTIVITY>
54.386700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-methylglutarate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0303007 (Methylglutamic acid)

HMDB0303007
     RDKit          3D
Methylglutamic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.1933   -0.9712    0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6312    0.4205    0.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235    0.3523   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4011   -0.5597   -0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574   -0.1827    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.9417    0.4896 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1836    0.9441    1.1026 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.7993    1.2685    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8779    0.6957   -0.2083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7897    2.6492    0.0541 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0062   -0.7877    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063   -1.3031   -0.1922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -1.6478    1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138    0.8289    1.2944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4742    1.3814   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445   -0.0298   -1.6506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460   -0.5064   -1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311   -1.6104   -0.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
M  CHG  2   7  -1  10  -1
M  END
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PDB for HMDB0303007 (Methylglutamic acid)

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       8.621   4.977   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.286   3.437   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O-1
CONECT    1    4                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    1    2    6                                                  
CONECT    5    3    7    8                                                  
CONECT    6    4    9   10                                                  
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0303007 (Methylglutamic acid)

COMPND    HMDB0303007
HETATM    1  C1  UNL     1      -1.193  -0.971   0.741  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.631   0.421   0.402  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.224   0.352  -0.834  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.401  -0.560  -0.743  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.357  -0.183   0.320  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.358  -0.942   0.490  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.184   0.944   1.103  1.00  0.00           O1-
HETATM    8  C6  UNL     1      -1.799   1.268   0.073  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.878   0.696  -0.208  1.00  0.00           O  
HETATM   10  O4  UNL     1      -1.790   2.649   0.054  1.00  0.00           O1-
HETATM   11  H1  UNL     1      -2.006  -0.788   1.467  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.706  -1.303  -0.192  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.412  -1.648   1.075  1.00  0.00           H  
HETATM   14  H4  UNL     1      -0.114   0.829   1.294  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.474   1.381  -1.118  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.444  -0.030  -1.651  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.946  -0.506  -1.713  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.031  -1.610  -0.559  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    8   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6    6    7
CONECT    8    9    9   10
END
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SMILES for HMDB0303007 (Methylglutamic acid)

CC(CCC([O-])=O)C([O-])=O
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INCHI for HMDB0303007 (Methylglutamic acid)

InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)/p-2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Methylglutaric acid(2-)Generator
MethylglutamateGenerator
Chemical FormulaC6H8O4
Average Molecular Weight144.127
Monoisotopic Molecular Weight144.043355897
IUPAC Name2-methylpentanedioate
Traditional Nameα-methylglutarate
CAS Registry NumberNot Available
SMILES
CC(CCC([O-])=O)C([O-])=O
InChI Identifier
InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)/p-2
InChI KeyAQYCMVICBNBXNA-UHFFFAOYSA-L
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP0.46ALOGPS
logP0.59ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area80.26 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.39 m³·mol⁻¹ChemAxon
Polarizability13.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+133.64432859911
AllCCS[M+H-H2O]+129.5432859911
AllCCS[M+Na]+138.56932859911
AllCCS[M+NH4]+137.46732859911
AllCCS[M-H]-125.42432859911
AllCCS[M+Na-2H]-127.55132859911
AllCCS[M+HCOO]-129.93532859911
DeepCCS[M+H]+130.7530932474
DeepCCS[M-H]-127.31630932474
DeepCCS[M-2H]-164.28230932474
DeepCCS[M+Na]+139.37130932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202210.6978 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.94 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1254.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid345.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid121.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid223.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid113.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid341.8 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 Acid377.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)106.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid791.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid292.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid960.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid227.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid300.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate554.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA220.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water280.7 seconds40023050

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylglutamic acid 10V, Positive-QTOFsplash10-0002-1900000000-346c88d7802fea12c8db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylglutamic acid 20V, Positive-QTOFsplash10-05oa-3900000000-47ba4b6c63e6f6ec66772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylglutamic acid 40V, Positive-QTOFsplash10-0a4i-9100000000-19bb5150bc8ccfb4be1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylglutamic acid 10V, Negative-QTOFsplash10-0f6x-1900000000-1a1b49d55ea3143dacf42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylglutamic acid 20V, Negative-QTOFsplash10-0zfr-5900000000-ad5093f8ae5dbe01c7312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylglutamic acid 40V, Negative-QTOFsplash10-0a4i-9100000000-d1f81a5bed69f6ac33fc2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007246
KNApSAcK IDNot Available
Chemspider ID11208317
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID84980
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 ReferencesNot Available