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Showing metabocard for N-Methyl-a-aminoisobutyric acid (HMDB0002141)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:38 UTC
Update Date2023-02-21 17:16:12 UTC
HMDB IDHMDB0002141
Secondary Accession Numbers
  • HMDB02141
Metabolite Identification
Common NameN-Methyl-a-aminoisobutyric acid
DescriptionN-Methyl-a-aminoisobutyric acid, also known as 2-(methylamino)isobutyrate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). N-Methyl-a-aminoisobutyric acid is a drug. N-Methyl-a-aminoisobutyric acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-methyl-a-aminoisobutyric acid a potential biomarker for the consumption of these foods. N-Methyl-a-aminoisobutyric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on N-Methyl-a-aminoisobutyric acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002141 (N-Methyl-a-aminoisobutyric acid)

  Mrv1652305271900232D          

  8  7  0  0  0  0            999 V2000
   14.9052   -7.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7302   -7.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1427   -8.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4927   -6.9306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1427   -6.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4927   -8.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9052   -6.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3177   -8.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  1  1  0  0  0  0
M  END
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3D MOL for HMDB0002141 (N-Methyl-a-aminoisobutyric acid)

HMDB0002141
     RDKit          3D
N-Methyl-a-aminoisobutyric acid
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.0794   -0.5101   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -0.1123   -1.0063 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162    0.0369   -0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -1.3100    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    1.1104    0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942    0.3958   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481    0.5186   -1.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493    0.6003    0.0180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    0.3737   -0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760   -1.1495    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433   -1.0912   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7297    0.4777   -1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653   -1.6102    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4453   -1.2875    1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804   -2.0517   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3960    2.0661    0.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0642    1.1759    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    0.8404    1.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0410    1.5268    0.1616 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  4 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  5 18  1  0
  8 19  1  0
M  END
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3D SDF for HMDB0002141 (N-Methyl-a-aminoisobutyric acid)

  Mrv1652305271900232D          

  8  7  0  0  0  0            999 V2000
   14.9052   -7.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7302   -7.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1427   -8.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4927   -6.9306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1427   -6.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4927   -8.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9052   -6.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3177   -8.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002141

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(C)(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H11NO2/c1-5(2,6-3)4(7)8/h6H,1-3H3,(H,7,8)

> <INCHI_KEY>
DLAMVQGYEVKIRE-UHFFFAOYSA-N

> <FORMULA>
C5H11NO2

> <MOLECULAR_WEIGHT>
117.1463

> <EXACT_MASS>
117.078978601

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
12.269741695022121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-2-(methylamino)propanoic acid

> <ALOGPS_LOGP>
-2.08

> <JCHEM_LOGP>
-2.1847592378162437

> <ALOGPS_LOGS>
0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.231033883397015

> <JCHEM_PKA_STRONGEST_BASIC>
10.522879122243074

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
29.9852

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(methylamino)isobutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0002141 (N-Methyl-a-aminoisobutyric acid)

HMDB0002141
     RDKit          3D
N-Methyl-a-aminoisobutyric acid
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.0794   -0.5101   -0.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -0.1123   -1.0063 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162    0.0369   -0.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4679   -1.3100    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326    1.1104    0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4942    0.3958   -0.7227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5481    0.5186   -1.9800 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493    0.6003    0.0180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    0.3737   -0.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0760   -1.1495    0.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433   -1.0912   -1.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7297    0.4777   -1.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653   -1.6102    1.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4453   -1.2875    1.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5804   -2.0517   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3960    2.0661    0.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0642    1.1759    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928    0.8404    1.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0410    1.5268    0.1616 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
  3  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  4 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  5 18  1  0
  8 19  1  0
M  END
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PDB for HMDB0002141 (N-Methyl-a-aminoisobutyric acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      27.823 -14.271   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.363 -14.271   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      30.133 -15.605   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      27.053 -12.937   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0      30.133 -12.937   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      27.053 -15.605   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.823 -11.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.593 -15.605   0.000  0.00  0.00           C+0
CONECT    1    2    4    6    8                                             
CONECT    2    1    3    5                                                  
CONECT    3    2                                                            
CONECT    4    1    7                                                       
CONECT    5    2                                                            
CONECT    6    1                                                            
CONECT    7    4                                                            
CONECT    8    1                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0002141 (N-Methyl-a-aminoisobutyric acid)

COMPND    HMDB0002141
HETATM    1  C1  UNL     1      -2.079  -0.510  -0.612  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.784  -0.112  -1.006  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.216   0.037  -0.031  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.468  -1.310   0.628  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.033   1.110   0.993  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.494   0.396  -0.723  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.548   0.519  -1.980  1.00  0.00           O  
HETATM    8  O2  UNL     1       2.649   0.600   0.018  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.756   0.374  -0.474  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.076  -1.149   0.264  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.543  -1.091  -1.458  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.730   0.478  -1.837  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.365  -1.610   1.259  1.00  0.00           H  
HETATM   14  H6  UNL     1       1.445  -1.288   1.150  1.00  0.00           H  
HETATM   15  H7  UNL     1       0.580  -2.052  -0.205  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.396   2.066   0.620  1.00  0.00           H  
HETATM   17  H9  UNL     1      -1.064   1.176   1.338  1.00  0.00           H  
HETATM   18  H10 UNL     1       0.593   0.840   1.893  1.00  0.00           H  
HETATM   19  H11 UNL     1       3.041   1.527   0.162  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12
CONECT    3    4    5    6
CONECT    4   13   14   15
CONECT    5   16   17   18
CONECT    6    7    7    8
CONECT    8   19
END
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SMILES for HMDB0002141 (N-Methyl-a-aminoisobutyric acid)

CNC(C)(C)C(O)=O
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INCHI for HMDB0002141 (N-Methyl-a-aminoisobutyric acid)

InChI=1S/C5H11NO2/c1-5(2,6-3)4(7)8/h6H,1-3H3,(H,7,8)
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Synonyms
Chemical FormulaC5H11NO2
Average Molecular Weight117.1463
Monoisotopic Molecular Weight117.078978601
IUPAC Name2-methyl-2-(methylamino)propanoic acid
Traditional Name2-(methylamino)isobutyric acid
CAS Registry Number2566-34-9
SMILES
CNC(C)(C)C(O)=O
InChI Identifier
InChI=1S/C5H11NO2/c1-5(2,6-3)4(7)8/h6H,1-3H3,(H,7,8)
InChI KeyDLAMVQGYEVKIRE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDDB08832
Phenol Explorer Compound IDNot Available
FooDB IDFDB022865
KNApSAcK IDNot Available
Chemspider ID68242
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6508
PubChem Compound6951124
PDB IDNot Available
ChEBI ID134261
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 References
  1. Thongsong B, Subramanian RK, Ganapathy V, Prasad PD: Inhibition of amino acid transport system a by interleukin-1beta in trophoblasts. J Soc Gynecol Investig. 2005 Oct;12(7):495-503. [PubMed:16202926 ]