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Human Metabolome Database Version 3.5

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Showing metabocard for D-Alpha-aminobutyric acid (HMDB00650)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:01 -0700
HMDB ID HMDB00650
Secondary Accession Numbers None
Metabolite Identification
Common Name D-Alpha-aminobutyric acid
Description D-alpha-aminobutyric acid is the D isomer of alpha-aminobutyric acid. The L-form of this amino acid is used in the biosynthesis of ophthalmic acid (a tripeptide analogue of glutathione in which the cysteine group is replaced by L-2-aminobutyrate, which was first discovered and isolated from calf lens). The D-form of this amino acid is a substrate for D-amino acid oxidase. There is little evidence that the D-form of this amino acid is found human biofluids or tissues however what little does exist likely is of bacterial origin.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2R)-2-aminobutanoate
  2. (2R)-2-aminobutanoic acid
  3. (R)-2-amino-Butanoate
  4. (R)-2-amino-Butanoic acid
  5. (R)-2-Aminobutanoate
  6. (R)-2-Aminobutanoic acid
  7. D-(-)-2-Aminobutyric acid
  8. D-2-Aminobutanoate
  9. D-2-Aminobutanoic acid
  10. D-2-Aminobuttersaeure
  11. D-2-Aminobutyrate
  12. D-2-Aminobutyric acid
  13. D-a-Aminobutyric acid
  14. D-alpha-Aminobutyric acid
  15. delta-(-)-2-Aminobutyric acid
  16. delta-2-Aminobutanoate
  17. delta-2-Aminobutanoic acid
  18. delta-2-Aminobuttersaeure
  19. delta-2-Aminobutyrate
  20. delta-2-Aminobutyric acid
  21. delta-alpha-Aminobutyric acid
Chemical Formula C4H9NO2
Average Molecular Weight 103.1198
Monoisotopic Molecular Weight 103.063328537
IUPAC Name (2R)-2-aminobutanoic acid
Traditional IUPAC Name α-aminobutyric acid
CAS Registry Number 2623-91-8
SMILES CC[C@@H](N)C(O)=O
InChI Identifier InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m1/s1
InChI Key QWCKQJZIFLGMSD-GSVOUGTGSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Amino fatty acids(KEGG)
  • Amino fatty acids(Lipidmaps)
  • D-alpha-amino acid(ChEBI)
  • alpha-aminobutyric acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 278 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 358 g/L ALOGPS
LogP -2.55 ALOGPS
LogP -2.3 ChemAxon
LogS 0.54 ALOGPS
pKa (strongest acidic) 2.62 ChemAxon
pKa (strongest basic) 9.53 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 63.32 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 25.02 ChemAxon
Polarizability 10.32 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
Urine Detected and Quantified
0.30 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012680
KNApSAcK ID Not Available
Chemspider ID 388757 Link_out
KEGG Compound ID C02261 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00650 Link_out
Metagene Link HMDB00650 Link_out
METLIN ID Not Available
PubChem Compound 439691 Link_out
PDB ID DBB Link_out
ChEBI ID 28797 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
  2. Ketting D, Wadman SK, Spaapen LJ, Van der Meer SB, Duran M: Gas chromatography method for the separation of amino acids enantiomers in plasma and urine. Application in a case of short bowel syndrome. Clin Chim Acta. 1991 Dec 31;204(1-3):79-86. Pubmed: 1819475 Link_out
  3. Lange R, Hui Bon Hoa G, Douzou P, Yagi K: Kinetics of primary interaction of D-amino acid oxidase with its substrate. Biochem Int. 1983 May;6(5):693-8. Pubmed: 6148943 Link_out