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Showing NP-Card for 3-Aminoisobutanoic acid (NP0000532)

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Record Information
Version1.0
Created at2006-08-13 07:07:14 UTC
Updated at2021-06-29 00:47:51 UTC
NP-MRD IDNP0000532
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Aminoisobutanoic acid
Description3-Aminoisobutanoic acid, also known as b-aminoisobutyrate or 2-methyl-beta-alanine, belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom. 3-Aminoisobutanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 3-Aminoisobutanoic acid exists in all eukaryotes, ranging from yeast to humans. 3-Aminoisobutanoic acid can be biosynthesized from ureidoisobutyric acid; which is mediated by the enzyme Beta-ureidopropionase. In humans, 3-aminoisobutanoic acid is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Beta-ureidopropionase deficiency is an inborn error of pyrimidine degradation associated with neurological abnormalities (OMIM 606673 ). 3-Aminoisobutanoic acid is a potentially toxic compound.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000532 (3-Aminoisobutanoic acid)


  Mrv1652305261923562D          

  7  6  0  0  0  0            999 V2000
   13.9949   -9.3080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2805   -8.0704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1370   -9.3080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5659   -9.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8515   -8.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5659  -10.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2805   -8.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
Download

3D MOL for NP0000532 (3-Aminoisobutanoic acid)

HMDB0003911
     RDKit          3D
3-Aminoisobutanoic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.1808   -1.7640    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930   -0.3497    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9016    0.2866   -0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191    1.6374   -0.4467 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820    0.3977    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226    0.8973    1.8502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823    0.5073   -0.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -1.6849   -0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -2.4121    0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6722   -2.1717   -0.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016   -0.3386    1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8150   -0.3175   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2617    0.1873   -1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    1.6594    0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    2.2697   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7239    1.1959   -0.2948 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
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3D SDF for NP0000532 (3-Aminoisobutanoic acid)


  Mrv1652305261923562D          

  7  6  0  0  0  0            999 V2000
   13.9949   -9.3080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2805   -8.0704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1370   -9.3080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5659   -9.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8515   -8.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5659  -10.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2805   -8.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  5  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CN)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)

> <INCHI_KEY>
QCHPKSFMDHPSNR-UHFFFAOYSA-N

> <FORMULA>
C4H9NO2

> <MOLECULAR_WEIGHT>
103.1198

> <EXACT_MASS>
103.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.42014399884362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-amino-2-methylpropanoic acid

> <ALOGPS_LOGP>
-2.97

> <JCHEM_LOGP>
-2.6306785728873137

> <ALOGPS_LOGS>
0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.17495406481514

> <JCHEM_PKA_STRONGEST_BASIC>
10.324199994995906

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
25.2773

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-β-aminoisobutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000532 (3-Aminoisobutanoic acid)

HMDB0003911
     RDKit          3D
3-Aminoisobutanoic acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -0.1808   -1.7640    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930   -0.3497    0.4669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9016    0.2866   -0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191    1.6374   -0.4467 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0820    0.3977    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226    0.8973    1.8502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9823    0.5073   -0.3304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0393   -1.6849   -0.6454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980   -2.4121    0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6722   -2.1717   -0.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016   -0.3386    1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8150   -0.3175   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2617    0.1873   -1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    1.6594    0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    2.2697   -0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7239    1.1959   -0.2948 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
Download

PDB for NP0000532 (3-Aminoisobutanoic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      26.124 -17.375   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      24.790 -15.065   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      20.789 -17.375   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      23.456 -17.375   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.123 -16.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.456 -18.915   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.790 -16.605   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    5                                                            
CONECT    4    5    6    7                                                  
CONECT    5    3    4                                                       
CONECT    6    4                                                            
CONECT    7    1    2    4                                                  
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
Download

3D PDB for NP0000532 (3-Aminoisobutanoic acid)

COMPND    HMDB0003911
HETATM    1  C1  UNL     1      -0.181  -1.764   0.062  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.193  -0.350   0.467  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.902   0.287  -0.684  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.319   1.637  -0.447  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.082   0.398   0.731  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.323   0.897   1.850  1.00  0.00           O  
HETATM    7  O2  UNL     1      -1.982   0.507  -0.330  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.039  -1.685  -0.645  1.00  0.00           H  
HETATM    9  H2  UNL     1      -0.398  -2.412   0.932  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.672  -2.172  -0.554  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.802  -0.339   1.378  1.00  0.00           H  
HETATM   12  H5  UNL     1       1.815  -0.317  -0.890  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.262   0.187  -1.578  1.00  0.00           H  
HETATM   14  H7  UNL     1       2.189   1.659   0.123  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.576   2.270  -0.120  1.00  0.00           H  
HETATM   16  H9  UNL     1      -2.724   1.196  -0.295  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    5   11
CONECT    3    4   12   13
CONECT    4   14   15
CONECT    5    6    6    7
CONECT    7   16
END
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SMILES for NP0000532 (3-Aminoisobutanoic acid)

CC(CN)C(O)=O
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INCHI for NP0000532 (3-Aminoisobutanoic acid)

InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
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Synonyms
ValueSource
2-(Aminomethyl)propionic acidChEBI
2-Methyl-beta-alanineChEBI
3-Amino-2-methylpropanoateChEBI
3-AminoisobutanoateChEBI
alpha-Methyl-beta-alanineChEBI
BAIBChEBI
beta-Aminoisobutyric acidChEBI
DL-beta-Aminoisobutyric acidChEBI
2-(Aminomethyl)propionateGenerator
2-Methyl-b-alanineGenerator
2-Methyl-β-alanineGenerator
3-Amino-2-methylpropanoic acidGenerator
a-Methyl-b-alanineGenerator
Α-methyl-β-alanineGenerator
b-AminoisobutyrateGenerator
b-Aminoisobutyric acidGenerator
beta-AminoisobutyrateGenerator
Β-aminoisobutyrateGenerator
Β-aminoisobutyric acidGenerator
DL-b-AminoisobutyrateGenerator
DL-b-Aminoisobutyric acidGenerator
DL-beta-AminoisobutyrateGenerator
DL-Β-aminoisobutyrateGenerator
DL-Β-aminoisobutyric acidGenerator
3-Aminoisobutyric acidHMDB
(+/-)-3-amino-2-methylpropanoateHMDB
(+/-)-3-amino-2-methylpropanoic acidHMDB
(+/-)-3-aminoisobutyric acidHMDB
(+/-)-b-aminoisobutyric acidHMDB
(+/-)-beta-aminoisobutyric acidHMDB
3-Amino-isobutanoateHMDB
3-Amino-isobutanoic acidHMDB
DL-2-Methyl-b-alanineHMDB
DL-2-Methyl-beta-alanineHMDB
DL-3-Amino-2-methylpropionic acidHMDB
DL-3-Aminoisobutyric acidHMDB
3-Aminoisobutyric acid, (+-)-isomerHMDB
DL-3-Aminoisobutyric acid monohydrateHMDB
3-Aminoisobutyric acid, (S)-isomerHMDB
3-Aminoisobutyric acid, tritium-labeledHMDB
3-Aminoisobutyric acid, (R)-isomerHMDB
3-AminoisobutyrateHMDB
3-Aminoisobutanoic acidChEBI
Chemical FormulaC4H9NO2
Average Mass103.1198 Da
Monoisotopic Mass103.06333 Da
IUPAC Name3-amino-2-methylpropanoic acid
Traditional Name(+)-β-aminoisobutyric acid
CAS Registry Number144-90-1
SMILES
CC(CN)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)
InChI KeyQCHPKSFMDHPSNR-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-10View Spectrum
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
Lunaria annuaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Salmonella entericaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility367 g/LALOGPS
logP-3ALOGPS
logP-2.6ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)4.17ChemAxon
pKa (Strongest Basic)10.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.28 m³·mol⁻¹ChemAxon
Polarizability10.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003911
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023248
KNApSAcK IDNot Available
Chemspider ID58481
KEGG Compound IDC05145
BioCyc ID3-AMINO-ISOBUTYRATE
BiGG ID41519
Wikipedia Link3-Aminoisobutyric_acid
METLIN ID5472
PubChem Compound64956
PDB IDNot Available
ChEBI ID27389
Good Scents IDNot Available
References
General References
  1. van Kuilenburg AB, Meinsma R, Beke E, Assmann B, Ribes A, Lorente I, Busch R, Mayatepek E, Abeling NG, van Cruchten A, Stroomer AE, van Lenthe H, Zoetekouw L, Kulik W, Hoffmann GF, Voit T, Wevers RA, Rutsch F, van Gennip AH: beta-Ureidopropionase deficiency: an inborn error of pyrimidine degradation associated with neurological abnormalities. Hum Mol Genet. 2004 Nov 15;13(22):2793-801. Epub 2004 Sep 22. [PubMed:15385443 ]
  2. Fornai M, Blandizzi C, Colucci R, Antonioli L, Bernardini N, Segnani C, Baragatti B, Barogi S, Berti P, Spisni R, Del Tacca M: Role of cyclooxygenases 1 and 2 in the modulation of neuromuscular functions in the distal colon of humans and mice. Gut. 2005 May;54(5):608-16. [PubMed:15831902 ]
  3. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
  4. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  5. Kuo KC, Cole TF, Gehrke CW, Waalkes TP, Borek E: Dual-column cation-exchange chromatographic method for beta-aminoisobutyric acid and beta-alanine in biological samples. Clin Chem. 1978 Aug;24(8):1373-80. [PubMed:679461 ]
  6. Jin LJ, Wang Y, Xu R, Go ML, Lee HK, Li SF: Chiral resolution of atropine, homatropine and eight synthetic tropinyl and piperidinyl esters by capillary zone electrophoresis with cyclodextrin additives. Electrophoresis. 1999 Jan;20(1):198-203. [PubMed:10065977 ]
  7. LeBlanc J: Nutritional implications of cephalic phase thermogenic responses. Appetite. 2000 Apr;34(2):214-6. [PubMed:10744912 ]
  8. Takeda H, Yamazaki Y, Akahane M, Igawa Y, Ajisawa Y, Nishizawa O: Role of the beta(3)-adrenoceptor in urine storage in the rat: comparison between the selective beta(3)-adrenoceptor agonist, CL316, 243, and various smooth muscle relaxants. J Pharmacol Exp Ther. 2000 Jun;293(3):939-45. [PubMed:10869395 ]
  9. Raufman JP, Chen Y, Zimniak P, Cheng K: Deoxycholic acid conjugates are muscarinic cholinergic receptor antagonists. Pharmacology. 2002 Aug;65(4):215-21. [PubMed:12119452 ]
  10. Joyner MJ, Dietz NM: Sympathetic vasodilation in human muscle. Acta Physiol Scand. 2003 Mar;177(3):329-36. [PubMed:12609003 ]
  11. Nelson CP, Gupta P, Napier CM, Nahorski SR, Challiss RA: Functional selectivity of muscarinic receptor antagonists for inhibition of M3-mediated phosphoinositide responses in guinea pig urinary bladder and submandibular salivary gland. J Pharmacol Exp Ther. 2004 Sep;310(3):1255-65. Epub 2004 May 12. [PubMed:15140916 ]
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