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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-03-29 12:26:15 UTC
Update Date2021-09-07 16:45:31 UTC
HMDB IDHMDB0001906
Secondary Accession Numbers
  • HMDB01906
Metabolite Identification
Common Name2-Aminoisobutyric acid
Description2-Aminoisobutyric acid, also known as alpha-methylalanine or a-aminoisobutanoate, 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). 2-Aminoisobutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Aminoisobutyric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2-Aminoisobutyric acid has been detected, but not quantified in cow milk. Aminoisobutyric 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
Data?1582752216
Synonyms
ValueSource
2,2-DimethylglycineChEBI
2-Amino-2-methylpropanoateChEBI
2-Amino-2-methylpropionic acidChEBI
2-MethylalanineChEBI
2MAChEBI
AIBChEBI
alpha,alpha-DimethylglycineChEBI
alpha-Aminoisobutanoic acidChEBI
alpha-Aminoisobutyric acidChEBI
alpha-MethylalanineChEBI
2-Amino-2-methylpropanoic acidGenerator
2-Amino-2-methylpropionateGenerator
a,a-DimethylglycineGenerator
Α,α-dimethylglycineGenerator
a-AminoisobutanoateGenerator
a-Aminoisobutanoic acidGenerator
alpha-AminoisobutanoateGenerator
Α-aminoisobutanoateGenerator
Α-aminoisobutanoic acidGenerator
a-AminoisobutyrateGenerator
a-Aminoisobutyric acidGenerator
alpha-AminoisobutyrateGenerator
Α-aminoisobutyrateGenerator
Α-aminoisobutyric acidGenerator
a-MethylalanineGenerator
Α-methylalanineGenerator
2-AminoisobutyrateGenerator
2-Aminoisobutyric acid, 11C-labeledHMDB
2-Aminoisobutyric acid, 14C-labeledHMDB
2-Amino-isobutyrateHMDB
2-Aminoisobutyric acidKEGG
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 KeyFUOOLUPWFVMBKG-UHFFFAOYSA-N
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
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point335 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility181 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility337 g/LALOGPS
logP-2.4ALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.21 m³·mol⁻¹ChemAxon
Polarizability10.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-ExperimentalNot Available129.44http://allccs.zhulab.cn/database/detail?ID=AllCCS00001778
AllCCS[M+H]+ExperimentalNot Available123.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00001778
DarkChem[M+H]+PredictedNot Available120.73131661259
DarkChem[M-H]-PredictedNot Available114.49131661259
AllCCS[M+H]+PredictedNot Available126.31732859911
AllCCS[M-H]-PredictedNot Available123.88932859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001i-0900000000-e469c31fdb361c68d7c12014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-0900000000-a36ad39a36ae444e46ae2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001i-0900000000-e469c31fdb361c68d7c12017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0900000000-a36ad39a36ae444e46ae2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-6b7bf93c06f2aeefce392017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9600000000-a300b153080dc92a72f62017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9000000000-c4f1b2912eeb0cb592ae2021-09-05View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb62021-09-18View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312ab2021-09-18View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9200000000-da2827369e92adba7cd82012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-7900000000-6079ac9d44cf4a3111522012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-4900000000-cf4a983a808aa8a187292012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-b09f9465bfd507f59a9d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-4eeda03ca057f971ad212012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-4900000000-8b7badd6f8457356fe622012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4i-9000000000-7e17058c19f5affb357a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-b986c9a42c2c739c6fd02012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-bf285168a5a5d41ab0492012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4l-9000000000-b7fd609f2bf6e6145d542012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0pb9-9500000000-2f9ed721c06843a9df2b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0900000000-02624b93137883b214ad2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-b09f9465bfd507f59a9d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-4eeda03ca057f971ad212017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-02624b93137883b214ad2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-aac342be2df7745c885d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-4900000000-8b7badd6f8457356fe622017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-23a671f383f99bc465c82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-b986c9a42c2c739c6fd02017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9200000000-4849dde814173ad8e73f2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-5ae41491e22202d700f32017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-6dff5b04f9cf69c4d6862017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-278a45a568ba95d65cab2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1900000000-82d99c3456fa9229a2242017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9i-9200000000-a1add3dee96321589e432017-07-26View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 400 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 QuantifiedNot SpecifiedBoth
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedChildren (6 - 18 years old)Not SpecifiedUnclassified IBD details
Associated Disorders and Diseases
Disease References
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Associated OMIM IDs
DrugBank IDDB02952
Phenol Explorer Compound IDNot Available
FooDB IDFDB022732
KNApSAcK IDNot Available
Chemspider ID5891
KEGG Compound IDC03665
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Aminoisobutyric acid
METLIN ID37
PubChem Compound6119
PDB IDNot Available
ChEBI ID27971
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:2037651 ]
  2. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  3. 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. [PubMed:14806475 ]
  4. HARRIS H: Family studies on the urinary excretion of beta-aminoisobutyric acid. Ann Eugen. 1953 Jun;18(1):43-9. [PubMed:13058271 ]