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Showing NP-Card for (2s,4r)-2-amino-4-methylpentanedioic acid (NP0198231)

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Record Information
Version2.0
Created at2022-09-04 16:38:52 UTC
Updated at2022-09-04 16:38:52 UTC
NP-MRD IDNP0198231
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,4r)-2-amino-4-methylpentanedioic acid
Description31137-74-3, Also known as 4-methylglutamate, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. (2s,4r)-2-amino-4-methylpentanedioic acid is found in Lathyrus japonicus. Based on a literature review very few articles have been published on 31137-74-3.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0198231 ((2s,4r)-2-amino-4-methylpentanedioic acid)


  Mrv1652309042218382D          

 11 10  0  0  1  0            999 V2000
    4.6184    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  2  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  2  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 N   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
    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  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
    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  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0198231 ((2s,4r)-2-amino-4-methylpentanedioic acid)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
    1.1675   -1.4305   -0.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2808   -0.0019    0.3527 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0120    0.7600    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891    0.1767    0.7889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3823   -1.1860    0.3425 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835    0.9563    0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4942    2.1986    0.5457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4030    0.3793   -0.4219 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3976    0.7086   -0.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003    1.7319   -1.0377 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7105    0.2468   -0.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7803   -2.1130    0.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758   -1.8263   -0.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5414   -1.5138   -1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -0.0203    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1848    1.8050    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1728    0.8818   -1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396    0.2666    1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1346   -1.2765   -0.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5671   -1.8368    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3497    0.3435   -0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3362    0.7501    0.4140 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
  4  6  1  0
  6  8  1  0
  6  7  2  0
  2  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  1
  3 16  1  0
  3 17  1  0
  4 18  1  1
  5 19  1  0
  5 20  1  0
  8 21  1  0
 11 22  1  0
M  END
Download

3D SDF for NP0198231 ((2s,4r)-2-amino-4-methylpentanedioic acid)


  Mrv1652309042218382D          

 11 10  0  0  1  0            999 V2000
    4.6184    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  2  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  2  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 N   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
    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  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
    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  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198231

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,4+/m1/s1

> <INCHI_KEY>
KRKRAOXTGDJWNI-DMTCNVIQSA-N

> <FORMULA>
C6H11NO4

> <MOLECULAR_WEIGHT>
161.157

> <EXACT_MASS>
161.068807838

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.152041679014625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4R)-2-amino-4-methylpentanedioic acid

> <JCHEM_LOGP>
-2.703641874600548

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.348167155630496

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0136227698929825

> <JCHEM_PKA_STRONGEST_BASIC>
9.528433520909388

> <JCHEM_POLAR_SURFACE_AREA>
100.62

> <JCHEM_REFRACTIVITY>
35.8622

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R)-2-amino-4-methylpentanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0198231 ((2s,4r)-2-amino-4-methylpentanedioic acid)

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PDB for NP0198231 ((2s,4r)-2-amino-4-methylpentanedioic acid)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.621   4.977   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.954   4.977   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.620   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+0
HETATM    9  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0198231 ((2s,4r)-2-amino-4-methylpentanedioic acid)
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SMILES for NP0198231 ((2s,4r)-2-amino-4-methylpentanedioic acid)
C[C@H](C[C@H](N)C(O)=O)C(O)=O
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INCHI for NP0198231 ((2s,4r)-2-amino-4-methylpentanedioic acid)
InChI=1S/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,4+/m1/s1
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View in JSmol
Synonyms
ValueSource
4-Methylglutamic acidMeSH
4-Methylglutamic acid, (L)-isomerMeSH
2S,4R-4-MethylglutamateMeSH
4-MethylglutamateMeSH
4-Methylglutamic acid, (DL)-isomerMeSH
4-Methylglutamic acid, 2-(13)C-labeled, (DL)-isomerMeSH
4-Methylglutamic acid, sodium salt, (erythro)-isomerMeSH
4-Methylglutamic acid, threo-(L)-isomerMeSH
Threo-gamma-methylglutamateMeSH
Chemical FormulaC6H11NO4
Average Mass161.1570 Da
Monoisotopic Mass161.06881 Da
IUPAC Name(2S,4R)-2-amino-4-methylpentanedioic acid
Traditional Name(2S,4R)-2-amino-4-methylpentanedioic acid
CAS Registry NumberNot Available
SMILES
C[C@H](C[C@H](N)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/t3-,4+/m1/s1
InChI KeyKRKRAOXTGDJWNI-DMTCNVIQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lathyrus japonicusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentL-alpha-amino acids  
Alternative Parents
Substituents
  • L-alpha-amino acid
    • 

  • Amino fatty acid
    • 

  • Branched fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP-2.7ChemAxon
pKa (Strongest Acidic)2.01ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.86 m³·mol⁻¹ChemAxon
Polarizability15.15 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 ID86558  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound95883  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]