Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:49 UTC
HMDB IDHMDB00056
Secondary Accession NumbersNone
Metabolite Identification
Common NameBeta-Alanine
DescriptionBeta-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.
Structure
Thumb
Synonyms
  1. 2-Carboxyethylamine
  2. 3-Amino-Propanoate
  3. 3-Amino-Propanoic acid
  4. 3-Aminopropanoate
  5. 3-Aminopropanoic acid
  6. 3-Aminopropionate
  7. 3-Aminopropionic acid
  8. Abufene
  9. B-Alanine
  10. b-Aminopropanoate
  11. b-Aminopropanoic acid
  12. b-Aminopropionate
  13. b-Aminopropionic acid
  14. beta Alanine
  15. beta-Alanine
  16. beta-Aminopropanoate
  17. beta-Aminopropanoic acid
  18. beta-Aminopropionate
  19. beta-Aminopropionic acid
  20. Omega-Aminopropionate
  21. Omega-Aminopropionic acid
Chemical FormulaC3H7NO2
Average Molecular Weight89.0932
Monoisotopic Molecular Weight89.047678473
IUPAC Name3-aminopropanoic acid
Traditional IUPAC Nameβ-alanine
CAS Registry Number107-95-9
SMILES
NCCC(O)=O
InChI Identifier
InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6)
InChI KeyUCMIRNVEIXFBKS-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassBeta Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Biogenic amines(KEGG)
  • Other amino acids(KEGG)
  • amino acid zwitterion(ChEBI)
Substituents
  • 1,3 Aminoalcohol
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentBeta Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Pantothenate and CoA biosynthesis
  • Component of Pyrimidine metabolism
  • Component of beta-Alanine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point200 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility545.0 mg/mLNot Available
LogP-3.05TSAI,RS ET AL. (1991)
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 area63.32ChemAxon
rotatable bond count2ChemAxon
refractivity20.7ChemAxon
polarizability8.62ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Kidney
  • Muscle
  • Pancreas
  • Placenta
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Aspartate MetabolismSMP00067map00250
Beta-Alanine MetabolismSMP00007map00410
Propanoate MetabolismSMP00016map00640
Pyrimidine MetabolismSMP00046map00240
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified3.0 (1.3-20.0) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified3.8 +/- 2.9 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified5.00 (0.00-10.00) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified3.00 +/- 0.85 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
BloodDetected and Quantified1.76 +/- 0.74 uMAdult (>18 years old)FemaleNormal
  • Geigy Scient...
BloodDetected and Quantified3.0 +/- 0.85 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified1.76 +/- 0.74 uMAdult (>18 years old)FemaleNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.024 +/- 0.013 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.03 (0.00-0.06) uMAdult (>18 years old)BothNormal
UrineDetected and Quantified2.4 +/- 3.0 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
UrineDetected and Quantified5.9 (3.4-13.0) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified1.27 +/- 0.9 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.8 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.23 +/- 0.73 umol/mmol creatinineInfant (0-1 year old)BothNormal
UrineDetected and Quantified0.00068 +/- 0.00049 umol/mmol creatinineAdult (>18 years old)MaleNormal
UrineDetected and Quantified0.0007 +/- 0.00075 umol/mmol creatinineAdult (>18 years old)FemaleNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified4.0 (0.9-6.2) uMAdult (>18 years old)BothDihydropyrimidine dehydrogenase (DPD) deficiency
BloodDetected and Quantified2.7 +/- 1.3 uMAdult (>18 years old)BothDihydropyrimidine dehydrogenase (DPD) deficiency
BloodDetected and Quantified23.0 uMChildren (1-13 year old)BothGABA transaminase deficiency
BloodDetected and Quantified107.5 (15.00-200.00) uMChildren (1-13 year old)BothHyper- beta-Alaninemia
Cerebrospinal Fluid (CSF)Detected and Quantified0.036 +/- 0.034 uMAdult (>18 years old)BothDihydropyrimidine dehydrogenase (DPD) deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified0.48 uMChildren (1-13 year old)BothGABA transaminase deficiency
Cerebrospinal Fluid (CSF)Detected and Quantified22.5 (0.00-45.00) uMChildren (1-13 year old)BothHyper- beta-Alaninemia
UrineDetected and Quantified1.4 +/- 1.4 umol/mmol creatinineAdult (>18 years old)BothDihydropyrimidine dehydrogenase (DPD) deficiency
UrineDetected and Quantified0.0-2.3 umol/mmol creatinineChildren (1-13 year old)BothGABA transaminase deficiency
Associated Disorders and Diseases
Disease References
Dihydropyrimidine dehydrogenase deficiency
  • 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. Pubmed: 14705962
Hyper beta-alaninemia
Gaba-transaminase deficiency
Associated OMIM IDs
    274270 (Dihydropyrimidine dehydrogenase deficiency)613163 (Gaba-transaminase deficiency)237400 (Hyper beta-alaninemia)
DrugBank IDDB03107
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB002253
KNApSAcK IDC00001333
Chemspider ID234
KEGG Compound IDC00099
BioCyc IDB-ALANINE
BiGG ID33848
Wikipedia Linkbeta-Alanine
NuGOwiki LinkHMDB00056
Metagene LinkHMDB00056
METLIN ID5119
PubChem Compound239
PDB IDBAL
ChEBI ID16958
References
Synthesis ReferenceBuc, Saul R.; Ford, Jared H.; Wise, E. C. Improved synthesis of b-alanine. Journal of the American Chemical Society (1945), 67 92-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  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. Pubmed: 19212411
  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. Pubmed: 14705962
  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. Pubmed: 2894959
  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. Pubmed: 9829262
  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. Pubmed: 7179210
  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. Pubmed: 15284084
  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. Pubmed: 679461
  9. 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. Pubmed: 3829006
  10. 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. Pubmed: 12067239
  11. 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. Pubmed: 3983897
  12. 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. Pubmed: 8203202
  13. 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. Pubmed: 16282220
  14. 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. Pubmed: 16554972
  15. 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. Pubmed: 2296474
  16. Karmanskii IM: [Effect of pepsin on low density serum lipoproteins] Vopr Med Khim. 1977 Jul-Aug;23(4):530-4. Pubmed: 200005
  17. 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. Pubmed: 2119585

Enzymes

Gene Name:
ABAT
Uniprot ID:
P80404
Reactions
Beta-Alanine + Oxoglutaric acid unknown Malonic semialdehyde + L-Glutamic aciddetails
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
ALDH2
Uniprot ID:
P05091
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
CNDP1
Uniprot ID:
Q96KN2
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Reactions
3-Aminopropionaldehyde + NAD + Water unknown Beta-Alanine + NADH + Hydrogen Iondetails
Gene Name:
UPB1
Uniprot ID:
Q9UBR1
Reactions
Ureidopropionic acid + Water unknown Beta-Alanine + CO(2) + Ammoniadetails
Ureidopropionic acid + Water unknown Beta-Alanine + Carbon dioxide + Ammoniadetails
Gene Name:
GAD2
Uniprot ID:
Q05329
Reactions
L-Aspartic acid unknown Beta-Alanine + Carbon dioxidedetails
Gene Name:
GAD1
Uniprot ID:
Q99259
Reactions
L-Aspartic acid unknown Beta-Alanine + Carbon dioxidedetails
Gene Name:
CARNS1
Uniprot ID:
A5YM72
Reactions
Adenosine triphosphate + L-Histidine + Beta-Alanine unknown ADP + Phosphoric acid + Carnosinedetails
Adenosine triphosphate + L-Lysine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + beta-Alanyl-L-lysinedetails
Adenosine triphosphate + L-Arginine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + beta-Alanyl-L-argininedetails
Adenosine triphosphate + L-Histidine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + Carnosinedetails
Adenosine triphosphate + 3-Methylhistidine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + Anserinedetails

Transporters

Gene Name:
SLC16A10
Uniprot ID:
Q8TF71