Record Information
Version1.0
Creation Date2014-08-29 06:30:45 UTC
Update Date2026-05-14 17:48:07 UTC
Accession NumberCHEM003306
Identification
Common NameBeta-Alanine
ClassSmall Molecule
Description
Beta-alanine is the only naturally occurring beta-amino acid - the amino group is at the β-position from the carboxylate group. It is formed in vivo by the degradation of dihydrouracil and carnosine. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (Vitamin B-5) which itself is a component of coenzyme A. Under normal conditions, beta-alanine is metabolized into acetic acid. Since neuronal uptake and neuronal receptor sensitivity to beta-alanine have been demonstrated, the compound may be a false transmitter replacing gamma-aminobutyric acid. A rare genetic disorder, hyper-beta-alaninemia, has been reported.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Synonyms
ValueSource
3-Aminopropanoic acidChEBI
3-Aminopropionic acidChEBI
BAlaChEBI
beta-Aminopropionic acidChEBI
H-beta-Ala-OHChEBI
Omega-aminopropionic acidChEBI
3-AminopropanoateKegg
AbufeneKegg
3-AminopropionateGenerator
b-AminopropionateGenerator
b-Aminopropionic acidGenerator
beta-AminopropionateGenerator
Β-aminopropionateGenerator
Β-aminopropionic acidGenerator
H-b-Ala-OHGenerator
H-Β-ala-OHGenerator
Omega-aminopropionateGenerator
b-AlanineGenerator
Β-alanineGenerator
2-CarboxyethylamineHMDB
3-Amino-propanoateHMDB
3-Amino-propanoic acidHMDB
b-AminopropanoateHMDB
b-Aminopropanoic acidHMDB
beta AlanineHMDB
beta-AminopropanoateHMDB
beta-Aminopropanoic acidHMDB
3 Aminopropionic acidHMDB
β-Aminopropanoic acidPhytoBank
omega-Aminopropanoic acidPhytoBank
ω-Aminopropanoic acidPhytoBank
ω-Aminopropionic acidPhytoBank
beta-AlaninePhytoBank
Chemical FormulaC3H7NO2
Average Molecular Mass89.093 g/mol
Monoisotopic Mass89.048 g/mol
CAS Registry Number107-95-9
IUPAC Name3-aminopropanoic acid
Traditional Nameβ alanine
SMILESNCCC(O)=O
InChI IdentifierInChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
InChI KeyUCMIRNVEIXFBKS-UHFFFAOYSA-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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Muscle
  • Pancreas
  • Placenta
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Aspartate MetabolismSMP00067 map00250
Beta-Alanine MetabolismSMP00007 map00410
Propanoate MetabolismSMP00016 map00640
Pyrimidine MetabolismSMP00046 map00240
GABA-Transaminase DeficiencySMP00351 Not Available
Methylmalonate Semialdehyde Dehydrogenase DeficiencySMP00384 Not Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point200°C
Boiling PointNot Available
Solubility545.0 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility494 g/LALOGPS
logP-3.3ALOGPS
logP-3.2ChemAxon
logS0.74ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
pKa (Strongest Basic)10.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.7 m³·mol⁻¹ChemAxon
Polarizability8.62 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsChronically high levels of beta-alanine are associated with at least 2 inborn errors of metabolism including: GABA-Transaminase Deficiency and Methylmalonate Semialdehyde Dehydrogenase Deficiency.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB03107
HMDB IDHMDB0000056
FooDB IDFDB002253
Phenol Explorer IDNot Available
KNApSAcK IDC00001333
BiGG ID33848
BioCyc IDB-ALANINE
METLIN ID5119
PDB IDNot Available
Wikipedia LinkBeta-Alanine
Chemspider ID234
ChEBI ID16958
PubChem Compound ID239
Kegg Compound IDC00099
YMDB IDYMDB00195
ECMDB IDECMDB00056
References
Synthesis Reference

Erwin Grill, Ernst-Ludwig Winnacker, Meinhart H. Zenk, “Cysteine-rich peptides having gamma-glutamic acid and beta-alanine units, a process for their preparation and their use.” U.S. Patent US4883861, issued March, 1978.

MSDSLink
General References
1. Buc, Saul R.; Ford, Jared H.; Wise, E. C. Improved synthesis of b-alanine. Journal of the American Chemical Society (1945), 67 92-4.
2. Buc, Saul R.; Ford, Jared H.; Wise, E. C. Improved synthesis of b-alanine. Journal of the American Chemical Society (1945), 67 92-4.
3. 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.
4. Malet-Martino MC, Bernadou J, Martino R, Armand JP: 19F NMR spectrometry evidence for bile acid conjugates of alpha-fluoro-beta-alanine as the main biliary metabolites of antineoplastic fluoropyrimidines in humans. Drug Metab Dispos. 1988 Jan-Feb;16(1):78-84.
5. Klebanov GI, Teselkin YuO, Babenkova IV, Lyubitsky OB, Rebrova OYu, Boldyrev AA, Vladimirov YuA: Effect of carnosine and its components on free-radical reactions. Membr Cell Biol. 1998;12(1):89-99.
6. Aznar J, Gilabert J, Estelles A, Fernandez MA, Villa P, Aznar JA: Evaluation of the soluble fibrin monomer complexes and other coagulation parameters in obstetric patients. Thromb Res. 1982 Sep 15;27(6):691-701.
7. Champion EE, Mann SJ, Glazier JD, Jones CJ, Rawlings JM, Sibley CP, Greenwood SL: System beta and system A amino acid transporters in the feline endotheliochorial placenta. Am J Physiol Regul Integr Comp Physiol. 2004 Dec;287(6):R1369-79. Epub 2004 Jul 29.
8. Kuo KC, Cole TF, Gehrke CW, Waalkes TP, Borek E: Dual-column cation-exchange chromatographic method for beta-aminoisobutyric acid and beta-alanine in biological samples. Clin Chem. 1978 Aug;24(8):1373-80.
9. 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.
10. Heggie GD, Sommadossi JP, Cross DS, Huster WJ, Diasio RB: Clinical pharmacokinetics of 5-fluorouracil and its metabolites in plasma, urine, and bile. Cancer Res. 1987 Apr 15;47(8):2203-6.
11. Gibson KM, Schor DS, Gupta M, Guerand WS, Senephansiri H, Burlingame TG, Bartels H, Hogema BM, Bottiglieri T, Froestl W, Snead OC, Grompe M, Jakobs C: Focal neurometabolic alterations in mice deficient for succinate semialdehyde dehydrogenase. J Neurochem. 2002 Apr;81(1):71-9.
12. Holm B, Nilsen DW, Kierulf P, Godal HC: Purification and characterization of 3 fibrinogens with different molecular weights obtained from normal human plasma. Thromb Res. 1985 Jan 1;37(1):165-76.
13. Chen Y, Getchell TV, Sparks DL, Getchell ML: Cellular localization of carnosinase in the human nasal mucosa. Acta Otolaryngol. 1994 Mar;114(2):193-8.
14. Milasta S, Pediani J, Appelbe S, Trim S, Wyatt M, Cox P, Fidock M, Milligan G: Interactions between the Mas-related receptors MrgD and MrgE alter signalling and trafficking of MrgD. Mol Pharmacol. 2006 Feb;69(2):479-91. Epub 2005 Nov 9.
15. Harris RC, Tallon MJ, Dunnett M, Boobis L, Coakley J, Kim HJ, Fallowfield JL, Hill CA, Sale C, Wise JA: The absorption of orally supplied beta-alanine and its effect on muscle carnosine synthesis in human vastus lateralis. Amino Acids. 2006 May;30(3):279-89. Epub 2006 Mar 24.
16. Hibbard JU, Pridjian G, Whitington PF, Moawad AH: Taurine transport in the in vitro perfused human placenta. Pediatr Res. 1990 Jan;27(1):80-4.
17. Karmanskii IM: [Effect of pepsin on low density serum lipoproteins]. Vopr Med Khim. 1977 Jul-Aug;23(4):530-4.
18. Johnson MR, Barnes S, Sweeny DJ, Diasio RB: 2-Fluoro-beta-alanine, a previously unrecognized substrate for bile acid coenzyme A:amino acid:N-acyltransferase from human liver. Biochem Pharmacol. 1990 Sep 15;40(6):1241-6.
19. 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.
20. Shetewy A, Shimada-Takaura K, Warner D, Jong CJ, Mehdi AB, Alexeyev M, Takahashi K, Schaffer SW: Mitochondrial defects associated with beta-alanine toxicity: relevance to hyper-beta-alaninemia. Mol Cell Biochem. 2016 May;416(1-2):11-22. doi: 10.1007/s11010-016-2688-z. Epub 2016 Mar 29.
21. 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.
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=11139233
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=11850512
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=12107759
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=12887142
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=14363188
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=16934791
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=18528519
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=18613640
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=19239140
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=19955842
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=20199122
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=20386120
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=20479615
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=20994958
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=22735334