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Showing NP-Card for N-Methyl-a-aminoisobutyric acid (NP0000396)

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Record Information
Version1.0
Created at2006-05-22 14:17:38 UTC
Updated at2021-06-29 00:47:23 UTC
NP-MRD IDNP0000396
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Methyl-a-aminoisobutyric acid
DescriptionN-Methyl-a-aminoisobutyric acid, also known as 2-(methylamino)isobutyrate or AMAIB, 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 is a metabolite that is actively incorporated into the cell by the actions of Interleukin 1-beta and Interleukin 6 via sodium dependent transport systems (PMID 16202926 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000396 (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 NP0000396 (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 NP0000396 (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>
NP0000396

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000396 (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 NP0000396 (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 NP0000396 (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 NP0000396 (N-Methyl-a-aminoisobutyric acid)

CNC(C)(C)C(O)=O
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INCHI for NP0000396 (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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View in JSmol
Synonyms
ValueSource
2-(Methylamino)isobutyric acidChEBI
2-(Methylamino)isobutyrateGenerator
N-Methyl-a-aminoisobutyrateGenerator
N-Methylaminoisobutyric acidHMDB
N-MethylaminoisobutyrateHMDB
N-Methyl-alpha-aminoisobutyrateHMDB
N-Methyl-alpha-aminoisobutyric acidHMDB
N-(Methylamino)isobutyric acidHMDB
AMAIBHMDB
N-Methyl alpha-aminoisobutyric acidHMDB
alpha-MethylaminoisobutyrateHMDB
alpha-(Methylamino)isobutyrateHMDB
a-(Methylamino)isobutyrateHMDB
a-(Methylamino)isobutyric acidHMDB
Α-(methylamino)isobutyrateHMDB
Α-(methylamino)isobutyric acidHMDB
N-Methyl-α-aminoisobutyrateHMDB
N-Methyl-α-aminoisobutyric acidHMDB
N-Methyl-a-aminoisobutyric acidGenerator
Chemical FormulaC5H11NO2
Average Mass117.1463 Da
Monoisotopic Mass117.07898 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility136 g/LALOGPS
logP-2.1ALOGPS
logP-2.2ChemAxon
logS0.06ALOGPS
pKa (Strongest Acidic)2.23ChemAxon
pKa (Strongest Basic)10.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity29.99 m³·mol⁻¹ChemAxon
Polarizability12.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002141
DrugBank IDDB08832
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  2. Schilling T, Eder C: A novel physiological mechanism of glycine-induced immunomodulation: Na+-coupled amino acid transporter currents in cultured brain macrophages. J Physiol. 2004 Aug 15;559(Pt 1):35-40. doi: 10.1113/jphysiol.2004.070763. Epub 2004 Jul 8. [PubMed:15243140 ]
  3. Tanaka K, Yamamoto A, Fujita T: Functional expression and adaptive regulation of Na+ -dependent neutral amino acid transporter SNAT2/ATA2 in normal human astrocytes under amino acid starved condition. Neurosci Lett. 2005 Apr 18;378(2):70-5. doi: 10.1016/j.neulet.2004.12.030. Epub 2005 Jan 13. [PubMed:15774260 ]
  4. Miyauchi S, Abbot EL, Zhuang L, Subramanian R, Ganapathy V, Thwaites DT: Isolation and function of the amino acid transporter PAT1 (slc36a1) from rabbit and discrimination between transport via PAT1 and system IMINO in renal brush-border membrane vesicles. Mol Membr Biol. 2005 Nov-Dec;22(6):549-59. doi: 10.1080/09687860500421779. [PubMed:16373326 ]
  5. Hatanaka T, Hatanaka Y, Setou M: Regulation of amino acid transporter ATA2 by ubiquitin ligase Nedd4-2. J Biol Chem. 2006 Nov 24;281(47):35922-30. doi: 10.1074/jbc.M606577200. Epub 2006 Sep 26. [PubMed:17003038 ]