Np mrd loader

Showing NP-Card for N-Methyl-L-aspartic acid (NP0002889)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2020-11-23 19:42:53 UTC
Updated at2021-08-12 19:52:26 UTC
NP-MRD IDNP0002889
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Methyl-L-aspartic acid
Provided ByBMRBBMRB logo
Description(2S)-2-(methylamino)butanedioic acid belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. It was first documented in 2005 (PMID: 16020277). Based on a literature review very few articles have been published on (2S)-2-(methylamino)butanedioic acid (PMID: 17984079) (PMID: 22290726).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002889 (N-Methyl-L-aspartic acid)


     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
    2.7885    0.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902    0.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4806   -0.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0450    1.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    2.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774    0.4689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289   -1.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8246   -1.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -3.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    2.2301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7188   -0.7666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869    0.6621    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689    2.2080    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7434   -1.2709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    1.7003    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396   -0.8065    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6402    1.2785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4496   -4.3194    0.0000 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
  3  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  6
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  1
  4 16  1  6
  4 17  1  0
  7 18  1  0
 10 19  1  0
M  END
Download

3D MOL for NP0002889 (N-Methyl-L-aspartic acid)

NP0002889
     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.8670   -1.6417   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784   -0.2765   -0.9730 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4796    0.1574   -0.0499 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8303   -0.5698   -0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446   -0.1000    0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -0.4683    1.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8103    0.8004    0.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2538    1.6135   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106    2.2804   -1.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    2.3044    0.5987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3319   -2.1837   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682   -2.1422   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -1.7035   -0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3275    0.3234   -0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8445   -0.0282    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260   -1.6641   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338   -0.4349   -1.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6124    0.4546   -0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901    3.2788    0.8119 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
  3  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  1
  4 16  1  0
  4 17  1  0
  7 18  1  0
 10 19  1  0
M  END
Download

3D SDF for NP0002889 (N-Methyl-L-aspartic acid)


     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
    2.7885    0.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2902    0.8014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4806   -0.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0450    1.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    2.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774    0.4689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3289   -1.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8246   -1.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3599   -3.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8582    2.2301    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7188   -0.7666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2869    0.6621    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7689    2.2080    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7434   -1.2709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    1.7003    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396   -0.8065    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6402    1.2785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4496   -4.3194    0.0000 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
  3  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  6
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  1
  4 16  1  6
  4 17  1  0
  7 18  1  0
 10 19  1  0
M  END
> <DATABASE_ID>
NP0002889

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m0/s1

> <INCHI_KEY>
HOKKHZGPKSLGJE-VKHMYHEASA-N

> <FORMULA>
C5H9NO4

> <MOLECULAR_WEIGHT>
147.13

> <EXACT_MASS>
147.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.179714417922114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(methylamino)butanedioic acid

> <JCHEM_LOGP>
-3.273642476612855

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.999787472023929

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.4571202479278575

> <JCHEM_PKA_STRONGEST_BASIC>
10.33837281139982

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
31.3073

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-methyl-L-aspartic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002889 (N-Methyl-L-aspartic acid)

NP0002889
     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.8670   -1.6417   -0.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4784   -0.2765   -0.9730 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4796    0.1574   -0.0499 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8303   -0.5698   -0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8446   -0.1000    0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -0.4683    1.9760 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8103    0.8004    0.3467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2538    1.6135   -0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106    2.2804   -1.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    2.3044    0.5987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3319   -2.1837   -0.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7682   -2.1422   -1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9424   -1.7035   -0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3275    0.3234   -0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8445   -0.0282    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260   -1.6641   -0.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338   -0.4349   -1.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6124    0.4546   -0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5901    3.2788    0.8119 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
  3  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  1
  4 16  1  0
  4 17  1  0
  7 18  1  0
 10 19  1  0
M  END
Download

PDB for NP0002889 (N-Methyl-L-aspartic acid)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.206   0.770   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       5.541   0.770   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.207  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    3    9   10                                                  
CONECT    6    1    3                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
Download

3D PDB for NP0002889 (N-Methyl-L-aspartic acid)

COMPND    NP0002889
HETATM    1  C1  UNL     1      -1.867  -1.642  -0.838  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.478  -0.276  -0.973  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.480   0.157  -0.050  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.830  -0.570  -0.199  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.845  -0.100   0.771  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.891  -0.468   1.976  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.810   0.800   0.347  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.254   1.614  -0.179  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.911   2.280  -1.023  1.00  0.00           O  
HETATM   10  O4  UNL     1       0.665   2.304   0.599  1.00  0.00           O  
HETATM   11  H1  UNL     1      -1.332  -2.184  -0.032  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.768  -2.142  -1.821  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.942  -1.704  -0.573  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.328   0.323  -0.980  1.00  0.00           H  
HETATM   15  H5  UNL     1      -0.845  -0.028   0.971  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.726  -1.664  -0.053  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.234  -0.435  -1.228  1.00  0.00           H  
HETATM   18  H8  UNL     1       3.612   0.455  -0.180  1.00  0.00           H  
HETATM   19  H9  UNL     1       0.590   3.279   0.812  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14
CONECT    3    4    8   15
CONECT    4    5   16   17
CONECT    5    6    6    7
CONECT    7   18
CONECT    8    9    9   10
CONECT   10   19
END
Download

SMILES for NP0002889 (N-Methyl-L-aspartic acid)

CN[C@@H](CC(O)=O)C(O)=O
Download

INCHI for NP0002889 (N-Methyl-L-aspartic acid)

InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
(2S)-2-(Methylamino)butanedioateGenerator
N-Methyl-L-aspartateGenerator
Chemical FormulaC5H9NO4
Average Mass147.1300 Da
Monoisotopic Mass147.05316 Da
IUPAC Name(2S)-2-(methylamino)butanedioic acid
Traditional NameN-methyl-L-aspartic acid
CAS Registry NumberNot Available
SMILES
CN[C@@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m0/s1
InChI KeyHOKKHZGPKSLGJE-VKHMYHEASA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Secondary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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-3.3ChemAxon
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)10.34ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.31 m³·mol⁻¹ChemAxon
Polarizability13.18 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 ID83935
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Nguyen DT, Kim KR, Lee G, Paik MJ: Chiral separation of N-methyl-DL-aspartic acid in rat brain tissue as N-ethoxycarbonylated (S)-(+)-2-octyl ester derivatives by GC-MS. Biomed Chromatogr. 2012 Nov;26(11):1353-6. doi: 10.1002/bmc.2703. Epub 2012 Jan 30. [PubMed:22290726 ]
  3. Tanaka M, Machida S, Ohtaka K, Tazawa Y, Nitta J: Third-order neuronal responses contribute to shaping the negative electroretinogram in sodium iodate-treated rats. Curr Eye Res. 2005 Jun;30(6):443-53. doi: 10.1080/02713680590959330. [PubMed:16020277 ]