| Record Information |
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| Version | 1.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2022-01-12 18:51:30 UTC |
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| NP-MRD ID | NP0000969 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | beta-Alanine |
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| Description | Beta-Alanine is the only naturally occurring beta-amino acid - an amino acid in which the amino group is at the beta-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. Beta-Alanine can undergo a transanimation reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis. Since neuronal uptake and neuronal receptor sensitivity to beta-alanine have been demonstrated, beta-alanine may act as a false transmitter replacing gamma-aminobutyric acid. When present in sufficiently high levels, beta-alanine can act as a neurotoxin, a mitochondrial toxin, and a metabotoxin. A neurotoxin is a compound that damages the brain or nerve tissue. A mitochondrial toxin is a compound that damages mitochondria and reduces cellular respiration as well as oxidative phosphorylation. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of beta-alanine are associated with at least three inborn errors of metabolism, including GABA-transaminase deficiency, hyper-beta-alaninemia, and methylmalonate semialdehyde dehydrogenase deficiency. Beta-Alanine is a central nervous system (CNS) depressant and is an inhibitor of GABA transaminase. The associated inhibition of GABA transaminase and displacement of GABA from CNS binding sites can also lead to GABAuria (high levels of GABA in the urine) and convulsions. In addition to its neurotoxicity, beta-alanine reduces cellular levels of taurine, which are required for normal respiratory chain function. Cellular taurine depletion is known to reduce respiratory function and elevate mitochondrial superoxide generation, which damages mitochondria and increases oxidative stress (PMID: 27023909 ). Individuals suffering from mitochondrial defects or mitochondrial toxicity typically develop neurotoxicity, hypotonia, respiratory distress, and cardiac failure. Beta-Alanine is a biomarker for the consumption of meat, especially red meat. |
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| Structure | InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6) |
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| Synonyms | | Value | Source |
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| 3-Aminopropanoic acid | ChEBI | | 3-Aminopropionic acid | ChEBI | | BAla | ChEBI | | beta-Aminopropionic acid | ChEBI | | H-beta-Ala-OH | ChEBI | | Omega-aminopropionic acid | ChEBI | | 3-Aminopropanoate | Kegg | | Abufene | Kegg | | 3-Aminopropionate | Generator | | b-Aminopropionate | Generator | | b-Aminopropionic acid | Generator | | beta-Aminopropionate | Generator | | Β-aminopropionate | Generator | | Β-aminopropionic acid | Generator | | H-b-Ala-OH | Generator | | H-Β-ala-OH | Generator | | Omega-aminopropionate | Generator | | b-Alanine | Generator | | Β-alanine | Generator | | 2-Carboxyethylamine | HMDB | | 3-Amino-propanoate | HMDB | | 3-Amino-propanoic acid | HMDB | | b-Aminopropanoate | HMDB | | b-Aminopropanoic acid | HMDB | | beta Alanine | HMDB | | beta-Aminopropanoate | HMDB | | beta-Aminopropanoic acid | HMDB | | 3 Aminopropionic acid | HMDB | | Β-aminopropanoic acid | HMDB | | Omega-aminopropanoic acid | HMDB | | Ω-aminopropanoic acid | HMDB | | Ω-aminopropionic acid | HMDB | | beta-Alanine | PhytoBank |
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| Chemical Formula | C3H7NO2 |
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| Average Mass | 89.0932 Da |
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| Monoisotopic Mass | 89.04768 Da |
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| IUPAC Name | 3-aminopropanoic acid |
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| Traditional Name | β alanine |
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| CAS Registry Number | 107-95-9 |
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| SMILES | NCCC(O)=O |
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| InChI Identifier | InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6) |
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| InChI Key | UCMIRNVEIXFBKS-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-12 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, experimental) | Ahselim | | | 2022-01-12 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | V.dorna83 | | | 2021-08-02 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Species Where Detected | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Beta amino acids and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 200 °C | Not Available | | Boiling Point | 237.00 to 238.00 °C. @ 760.00 mm Hg (est) | The Good Scents Company Information System | | Water Solubility | 545 mg/mL | Not Available | | LogP | -3.05 | Tsai, R. S., Testa, B., El Tayar, N., & Carrupt, P. A. (1991). Structure-lipophilicity relationships of zwitterionic amino acids. Journal of the Chemical Society, Perkin Transactions 2, (11), 1797-1802. |
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| Predicted Properties | |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Karmanskii IM: [Effect of pepsin on low density serum lipoproteins]. Vopr Med Khim. 1977 Jul-Aug;23(4):530-4. [PubMed:200005 ]
- 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 ]
- 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. [PubMed:27023909 ]
- Santos L, Goncalves LS, Bagheri-Hanei S, Moller GB, Sale C, James RM, Artioli GG: Insulin stimulates beta-alanine uptake in skeletal muscle cells in vitro. Amino Acids. 2021 Nov;53(11):1763-1766. doi: 10.1007/s00726-021-03090-9. Epub 2021 Oct 21. [PubMed:34676442 ]
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