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Record Information
Version3.6
Creation Date2006-03-29 12:26:15 UTC
Update Date2016-09-22 21:06:39 UTC
HMDB IDHMDB01906
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Aminoisobutyric acid
DescriptionAminoisobutyric acid is a nonprotein amino acid (is an end product of pyrimidine metabolism) excreted in the urine of about 5% of healthy individuals (PMID 14806475 ), and high excretion is an autosomal recessive phenotype (PMID 13058271 ).
Structure
Thumb
Synonyms
ValueSource
2-amino-2-MethylpropanoateHMDB
2-amino-2-Methylpropanoic acidHMDB
2-AminoisobutyrateHMDB
2-MethylalanineHMDB
a-AminoisobutanoateHMDB
a-Aminoisobutanoic acidHMDB
a-AminoisobutyrateHMDB
a-Aminoisobutyric acidHMDB
a-MethylalanineHMDB
AIBHMDB
alpha-AminoisobutanoateHMDB
alpha-Aminoisobutanoic acidHMDB
alpha-AminoisobutyrateHMDB
alpha-Aminoisobutyric acidHMDB
alpha-MethylalanineHMDB
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name2-amino-2-methylpropanoic acid
Traditional Nameα-aminoisobutyric acid
CAS Registry Number62-57-7
SMILES
CC(C)(N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)
InChI KeyInChIKey=FUOOLUPWFVMBKG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • D-alpha-amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point335 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility181 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility337.0 mg/mLALOGPS
logP-2.5ALOGPS
logP-2.4ChemAxon
logS0.51ALOGPS
pKa (Strongest Acidic)2.58ChemAxon
pKa (Strongest Basic)9.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.21 m3·mol-1ChemAxon
Polarizability10.33 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-001i-0900000000-e469c31fdb361c68d7c1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-0900000000-a36ad39a36ae444e46aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9200000000-da2827369e92adba7cd8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-7900000000-6079ac9d44cf4a311152View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-4900000000-cf4a983a808aa8a18729View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-b09f9465bfd507f59a9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-4eeda03ca057f971ad21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-4900000000-8b7badd6f8457356fe62View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4i-9000000000-7e17058c19f5affb357aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-b986c9a42c2c739c6fd0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-bf285168a5a5d41ab049View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4l-9000000000-b7fd609f2bf6e6145d54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0pb9-9500000000-2f9ed721c06843a9df2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-02624b93137883b214adView in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.03 +/- 0.34 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
BloodDetected and Quantified0.75 +/- 0.33 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedBoth
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022732
KNApSAcK IDNot Available
Chemspider ID5891
KEGG Compound IDC03665
BioCyc IDCPD-17880
BiGG IDNot Available
Wikipedia Link2-Aminoisobutyric acid
NuGOwiki LinkHMDB01906
Metagene LinkHMDB01906
METLIN ID37
PubChem Compound6119
PDB IDAIB
ChEBI ID27971
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. [19212411 ]
  2. Lucarelli C, Betto P, Ricciarello G, Grossi G: High-performance liquid chromatographic determination of L-3-(3,4-dihydroxyphenyl)-2-methylalanine (alpha-methyldopa) in human urine and plasma. J Chromatogr. 1991 Mar 22;541(1-2):285-96. [2037651 ]
  3. HARRIS H: Family studies on the urinary excretion of beta-aminoisobutyric acid. Ann Eugen. 1953 Jun;18(1):43-9. [13058271 ]
  4. CRUMPLER HR, DENT CE, HARRIS H, WESTALL RG: beta-Aminoisobutyric acid (alpha-methyl-beta-alanine); a new amino-acid obtained from human urine. Nature. 1951 Feb 24;167(4243):307-8. [14806475 ]