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Showing metabocard for (R)-beta-Aminoisobutyric acid (HMDB0002299)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:47 UTC
Update Date2021-09-14 15:00:09 UTC
HMDB IDHMDB0002299
Secondary Accession Numbers
  • HMDB02299
Metabolite Identification
Common Name(R)-beta-Aminoisobutyric acid
Description(R)-beta-Aminoisobutyric acid, also known as (R)-b-aminoisobutyrate or D-3-amino-isobutanoate, 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 (R)-beta-Aminoisobutyric acid exists in all living organisms, ranging from bacteria to humans (R)-beta-Aminoisobutyric acid has been detected, but not quantified in, several different foods, such as mountain yams (Dioscorea pentaphylla), chia (Salvia hispanica), passion fruits (Passiflora edulis), mammee apples (Mammea americana), and peanuts (Arachis hypogaea). This could make (R)-beta-aminoisobutyric acid a potential biomarker for the consumption of these foods (R)-beta-Aminoisobutyric acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on (R)-beta-Aminoisobutyric acid.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002299 ((R)-beta-Aminoisobutyric acid)

      
  Mrv1652303071919452D          

  7  6  0  0  1  0            999 V2000
   21.3917  -14.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1061  -13.4073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2496  -14.6450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8207  -14.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.5351  -14.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8207  -15.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1061  -14.2323    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  1  0  0  0
  4  7  1  0  0  0  0
M  END
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3D MOL for HMDB0002299 ((R)-beta-Aminoisobutyric acid)

HMDB0002299
     RDKit          3D
(R)-beta-Aminoisobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    0.1220    1.2040    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2164    0.4632   -0.3452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1333   -0.0413   -0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -0.9392    0.1849 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -0.5921   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0377   -1.8040   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5687   -0.2053   -0.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8139    1.7872    0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9535    1.9491    1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685    0.5303    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319    1.2104   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883   -0.5471   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    0.8327   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027   -1.5517   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875   -1.5546    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051   -0.7416    0.4695 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  6
  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 HMDB0002299 ((R)-beta-Aminoisobutyric acid)

      
  Mrv1652303071919452D          

  7  6  0  0  1  0            999 V2000
   21.3917  -14.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1061  -13.4073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2496  -14.6450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8207  -14.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.5351  -14.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8207  -15.4700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1061  -14.2323    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  1  0  0  0
  4  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002299

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1

> <INCHI_KEY>
QCHPKSFMDHPSNR-GSVOUGTGSA-N

> <FORMULA>
C4H9NO2

> <MOLECULAR_WEIGHT>
103.1198

> <EXACT_MASS>
103.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.435269853677193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-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>
25.277300000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e+02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002299 ((R)-beta-Aminoisobutyric acid)

HMDB0002299
     RDKit          3D
(R)-beta-Aminoisobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    0.1220    1.2040    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2164    0.4632   -0.3452 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1333   -0.0413   -0.7478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7343   -0.9392    0.1849 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2563   -0.5921   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0377   -1.8040   -0.5280 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5687   -0.2053   -0.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8139    1.7872    0.9655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9535    1.9491    1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1685    0.5303    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319    1.2104   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883   -0.5471   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8001    0.8327   -0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027   -1.5517   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875   -1.5546    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051   -0.7416    0.4695 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  6
  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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PDB for HMDB0002299 ((R)-beta-Aminoisobutyric acid)

HEADER    PROTEIN                                 07-MAR-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAR-19         0                                  
HETATM    1  O   UNK     0      39.931 -27.337   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      41.265 -25.027   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      45.266 -27.337   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      42.599 -27.337   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      43.932 -26.567   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.599 -28.877   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.265 -26.567   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
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3D PDB for HMDB0002299 ((R)-beta-Aminoisobutyric acid)

COMPND    HMDB0002299
HETATM    1  C1  UNL     1       0.122   1.204   0.962  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.216   0.463  -0.345  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.133  -0.041  -0.748  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.734  -0.939   0.185  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.256  -0.592  -0.337  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.038  -1.804  -0.528  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.569  -0.205  -0.101  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.814   1.787   0.965  1.00  0.00           H  
HETATM    9  H2  UNL     1       0.953   1.949   1.017  1.00  0.00           H  
HETATM   10  H3  UNL     1       0.168   0.530   1.838  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.532   1.210  -1.112  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.088  -0.547  -1.740  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.800   0.833  -0.886  1.00  0.00           H  
HETATM   14  H7  UNL     1      -2.403  -1.552  -0.334  1.00  0.00           H  
HETATM   15  H8  UNL     1      -1.087  -1.555   0.694  1.00  0.00           H  
HETATM   16  H9  UNL     1       3.205  -0.742   0.469  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 HMDB0002299 ((R)-beta-Aminoisobutyric acid)

C[C@H](CN)C(O)=O
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INCHI for HMDB0002299 ((R)-beta-Aminoisobutyric acid)

InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name(2R)-3-amino-2-methylpropanoic acid
Traditional Name(R)-β-aminoisobutyric acid
CAS Registry Number2140-95-6
SMILES
C[C@H](CN)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-3(2-5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1
InChI KeyQCHPKSFMDHPSNR-GSVOUGTGSA-N
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot 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
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022955
KNApSAcK IDNot Available
Chemspider ID4573585
KEGG Compound IDC01205
BioCyc IDCPD-471
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6599
PubChem Compound5459822
PDB IDNot Available
ChEBI ID16320
Food Biomarker OntologyNot Available
VMH ID3AIB_D
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferencePollock, Glenn. Preparation of R(-)-b-aminoisobutyric acid using Saccharomyces cerevisiae. Unexpected result. Analytical Biochemistry (1974), 57(1), 82-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105. [PubMed:10686279 ]
  2. Van Kuilenburg AB, Stroomer AE, Van Lenthe H, Abeling NG, Van Gennip AH: New insights in dihydropyrimidine dehydrogenase deficiency: a pivotal role for beta-aminoisobutyric acid? Biochem J. 2004 Apr 1;379(Pt 1):119-24. [PubMed:14705962 ]

Enzymes

Enzyme Details
1. Alanine--glyoxylate aminotransferase 2, mitochondrial
General function:
Involved in transaminase activity
Specific function:
Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
Gene Name:
AGXT2
Uniprot ID:
Q9BYV1
Molecular weight:
57155.905
Reactions
(R)-beta-Aminoisobutyric acid + Pyruvic acid → 2-Methyl-3-oxopropanoic acid + L-Alaninedetails