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Record Information
StatusDetected and Quantified
Creation Date2006-08-13 07:07:14 UTC
Update Date2020-10-09 21:03:20 UTC
Secondary Accession Numbers
  • HMDB0000485
  • HMDB00485
  • HMDB03911
Metabolite 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.
2-(Aminomethyl)propionic acidChEBI
beta-Aminoisobutyric acidChEBI
DL-beta-Aminoisobutyric acidChEBI
3-Amino-2-methylpropanoic acidGenerator
b-Aminoisobutyric acidGenerator
Β-aminoisobutyric acidGenerator
DL-b-Aminoisobutyric acidGenerator
DL-Β-aminoisobutyric acidGenerator
3-Aminoisobutyric acidHMDB
(+/-)-3-amino-2-methylpropanoic acidHMDB
(+/-)-3-aminoisobutyric acidHMDB
(+/-)-b-aminoisobutyric acidHMDB
(+/-)-beta-aminoisobutyric acidHMDB
3-Amino-isobutanoic acidHMDB
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-Aminoisobutanoic acidChEBI
Chemical FormulaC4H9NO2
Average Molecular Weight103.1198
Monoisotopic Molecular Weight103.063328537
IUPAC Name3-amino-2-methylpropanoic acid
Traditional Name(+)-β-aminoisobutyric acid
CAS Registry Number144-90-1
InChI Identifier
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
  • 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


Biological location:


Naturally occurring process:


Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility367 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-3900000000-9d996f1ef303093bc6f2Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-1900000000-599e217ab2fffbcaedcfSpectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2920000000-235394017181e4a1ccc4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2920000000-235394017181e4a1ccc4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-3900000000-9d996f1ef303093bc6f2Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-1900000000-599e217ab2fffbcaedcfSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-2900000000-83730a256456aac8055aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0900000000-ecf6ec14beb319448103Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-89dae4e73d997d89e2e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ar-9200000000-0eb92539979a9fa36dbdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9200000000-1212facd6e8f1c4ede25Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-6900000000-8b7d740c75c426976897Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-4900000000-68b30ab5196763854bfbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udr-5900000000-d8bec01eb9aa047f87d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-2900000000-d13f4bc606699ca79bdaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-2900000000-d13f4bc606699ca79bdaSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0uk9-5900000000-7eb5bc6532d9dac5e48fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udr-5900000000-d8bec01eb9aa047f87d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udr-9600000000-62b406ac77af506e283fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-9400000000-e80e2eb321cf19f4e299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-9000000000-9649dec1f6afdd5b12c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-aaf9fc6ded63400c1d6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-6f58da61e2ae030dbbadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9600000000-ba32a8e8fca536c36023Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-e756dcf352426858cb71Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Normal Concentrations
BloodDetected and Quantified1.8-4.5 uMNewborn (0-30 days old)Not SpecifiedNormal details
BloodDetected and Quantified1.03 +/- 0.34 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.75 +/- 0.33 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
UrineDetected and Quantified2.71-57.80 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified300-390 umol/mmol creatinineNewborn (0-30 days old)Both
UrineDetected and Quantified3.6-13 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified5.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.24-32.35 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal details
UrineDetected and Quantified9.73 +/- 9.20 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
UrineDetected and Quantified7.20 +/- 6.73 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
UrineDetected and Quantified34.288 +/- 32.202 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    • Mordechai, Hien, ...
UrineDetected and Quantified2.91-116.43 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
UrineDetected and Quantified<34.048 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
UrineDetected and Quantified2.04-354.79 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified4.3-8.5 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified6.81 +/- 2.82 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified25.8 (1.4-155.6) umol/mmol creatinineAdult (>18 years old)Both
UrineDetected and Quantified<110.86 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified1.70-117.53 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
UrineDetected and Quantified25.9 (2.2-140.0) umol/mmol creatinineAdult (>18 years old)Both
Abnormal Concentrations
BloodDetected and Quantified30 +/- 6 uMNewborn (0-30 days old)MaleMethylmalonate semialdehyde dehydrogenase deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
UrineDetected and Quantified60.338 +/- 80.333 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
UrineDetected and Quantified248.732 umol/mmol creatinineChildren (1-13 years old)MaleD-Lactic Acidosis details
Associated Disorders and Diseases
Disease References
Methylmalonate semialdehyde dehydrogenase deficiency
  1. Pollitt RJ, Green A, Smith R: Excessive excretion of beta-alanine and of 3-hydroxypropionic, R- and S-3-aminoisobutyric, R- and S-3-hydroxyisobutyric and S-2-(hydroxymethyl)butyric acids probably due to a defect in the metabolism of the corresponding malonic semialdehydes. J Inherit Metab Dis. 1985;8(2):75-9. [PubMed:3939535 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
D-Lactic Acidosis
  1. Duran M, Van Biervliet JP, Kamerling JP, Wadman SK: D-lactic aciduria, an inborn error of metabolism? Clin Chim Acta. 1977 Feb 1;74(3):297-300. [PubMed:832430 ]
Associated OMIM IDs
  • 614105 (Methylmalonate semialdehyde dehydrogenase deficiency)
  • 114500 (Colorectal cancer)
  • 610247 (Eosinophilic esophagitis)
  • 245450 (D-Lactic Acidosis)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023248
KNApSAcK IDNot Available
Chemspider ID58481
KEGG Compound IDC05145
BiGG ID41519
Wikipedia Link3-Aminoisobutyric_acid
PubChem Compound64956
PDB IDNot Available
ChEBI ID27389
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000435
Synthesis ReferenceBalenovic, K.; Jambresic, I.; Ranogajec, I. Preparation of b-aminoisobutyric acid from glycine via the Wolff rearrangement of diazoethyl ketones. Croatica Chemica Acta (1957), 29 87-92.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  7. 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 ]
  8. 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 ]
  9. Jooste EH, Sharma A, Zhang Y, Emala CW: Rapacuronium augments acetylcholine-induced bronchoconstriction via positive allosteric interactions at the M3 muscarinic receptor. Anesthesiology. 2005 Dec;103(6):1195-203. [PubMed:16306732 ]
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  11. Carnicella S, de Vasconcelos AP, Pain L, Majchrzak M, Oberling P: Fos immunolabelling evidence for brain regions involved in the Pavlovian degraded contingency effect and in its disruption by atropine. Neuropharmacology. 2006 Jul;51(1):102-11. Epub 2006 May 6. [PubMed:16678862 ]
  12. Hu J, DeChon J, Yan KC, Liu Q, Hu G, Wu J: Iptakalim inhibits nicotinic acetylcholine receptor-mediated currents in dopamine neurons acutely dissociated from rat substantia nigra pars compacta. Neurosci Lett. 2006 Jul 31;403(1-2):57-62. Epub 2006 May 26. [PubMed:16730119 ]
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  14. 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 ]
  15. Salminen L: Review: systemic absorption of topically applied ocular drugs in humans. J Ocul Pharmacol. 1990 Fall;6(3):243-9. [PubMed:2290070 ]
  16. Watson GE, Pearson SK, Falany JL, Culp DJ, Tabak LA, Bowen WH: The effect of chronic atropine treatment on salivary composition and caries in rats. J Dent Res. 1989 Dec;68(12):1739-45. [PubMed:2600253 ]
  17. Foster WM, Bergofsky EH: Airway mucus membrane: effects of beta-adrenergic and anticholinergic stimulation. Am J Med. 1986 Nov 14;81(5A):28-35. [PubMed:2878612 ]
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  20. Kusunoki M, Yamamura T, Takahashi T, Kantoh M, Ishikawa Y, Utsunomiya J: Choledochal cyst. Its possible autonomic involvement in the bile duct. Arch Surg. 1987 Sep;122(9):997-1000. [PubMed:3619630 ]
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  29. Andersson K, Arner P: Cholinoceptor-mediated effects on glycerol output from human adipose tissue using in situ microdialysis. Br J Pharmacol. 1995 Aug;115(7):1155-62. [PubMed:7582538 ]
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  33. 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 ]
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  35. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]


General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
Specific function:
Converts N-carbamyl-beta-aminoisobutyric acid and N-carbamyl-beta-alanine to, respectively, beta-aminoisobutyric acid and beta-alanine, ammonia and carbon dioxide.
Gene Name:
Uniprot ID:
Molecular weight:
Ureidoisobutyric acid + Water → 3-Aminoisobutanoic acid + Carbon dioxide + Ammoniadetails