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Showing NP-Card for Methylglutamic acid (NP0333863)

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Record Information
Version2.0
Created at2024-09-09 21:00:01 UTC
Updated at2024-09-09 21:00:01 UTC
NP-MRD IDNP0333863
Secondary Accession NumbersNone
Natural Product 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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MOLSDFPDBSMILESInChI

MOL for NP0333863 (Methylglutamic acid)


  Mrv2104 05242323322D          

 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
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
M  CHG  2   8  -1  10  -1
M  END
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3D MOL for NP0333863 (Methylglutamic acid)

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3D SDF for NP0333863 (Methylglutamic acid)

  Mrv2104 05242323322D          

 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
  1  4  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  2  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
M  CHG  2   8  -1  10  -1
M  END
> <DATABASE_ID>
NP0333863

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1/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-UHFFFAOYNA-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

> <JCHEM_LOGP>
0.5890719759999997

> <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

> <JCHEM_TRADITIONAL_IUPAC>
α-methylglutarate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0333863 (Methylglutamic acid)
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PDB for NP0333863 (Methylglutamic acid)
HEADER    PROTEIN                                 24-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-MAY-23         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 NP0333863 (Methylglutamic acid)
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SMILES for NP0333863 (Methylglutamic acid)
CC(CCC([O-])=O)C([O-])=O
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INCHI for NP0333863 (Methylglutamic acid)
InChI=1/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 JSmol
Synonyms
ValueSource
MethylglutamateGenerator
Chemical FormulaC6H8O4
Average Mass144.1270 Da
Monoisotopic Mass144.04336 Da
IUPAC Name2-methylpentanedioate
Traditional Nameα-methylglutarate
CAS Registry NumberNot Available
SMILES
CC(CCC([O-])=O)C([O-])=O
InChI Identifier
InChI=1/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-UHFFFAOYNA-L
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.59ChemAxon
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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methyl-L-glutamic acid  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Xu B, Hermant Y, Yang SH, Harris PWR, Brimble MA: A Versatile Boc Solid Phase Synthesis of Daptomycin and Analogues Using Site Specific, On-Resin Ozonolysis to Install the Kynurenine Residue. Chemistry. 2019 Nov 7;25(62):14101-14107. doi: 10.1002/chem.201903725. Epub 2019  Sep 30. [PubMed:31429133  ] 
  2. Heisel LS, Andersen FD, Joca S, Sorensen LK, Simonsen U, Hasselstrom JB, Andersen CU, Nielsen KL: Combined in vivo metabolic effects of quetiapine and methadone in brain and blood of rats. Arch Toxicol. 2024 Jan;98(1):289-301. doi: 10.1007/s00204-023-03620-2. Epub 2023  Oct 23. [PubMed:37870577  ] 
  3. India Aldana S, Valvi D, Joshi A, Lucchini RG, Placidi D, Petrick L, Horton M, Niedzwiecki M, Colicino E: Salivary Metabolomic Signatures and Body Mass Index in Italian Adolescents: A Pilot Study. J Endocr Soc. 2023 Jul 1;7(8):bvad091. doi: 10.1210/jendso/bvad091. eCollection  2023 Jul 3. [PubMed:37457847  ] 
  4. Koga R, Miyoshi Y, Negishi E, Kaneko T, Mita M, Lindner W, Hamase K: Enantioselective two-dimensional high-performance liquid chromatographic determination of N-methyl-D-aspartic acid and its analogues in mammals and bivalves. J Chromatogr A. 2012 Dec 21;1269:255-61. doi: 10.1016/j.chroma.2012.08.075. Epub  2012 Aug 31. [PubMed:22999197  ]