Beta-Alanine
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Basic Info
| Common Name | Beta-Alanine(F05346) |
| 2D Structure | |
| 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. |
| FRCD ID | F05346 |
| CAS Number | 107-95-9 |
| PubChem CID | 239 |
| Formula | C3H7NO2 |
| IUPAC Name | 3-aminopropanoic acid |
| InChI Key | UCMIRNVEIXFBKS-UHFFFAOYSA-N |
| InChI | InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6) |
| Canonical SMILES | C(CN)C(=O)O |
| Isomeric SMILES | C(CN)C(=O)O |
| Wikipedia | Beta-Alanine |
| Synonyms |
3-Aminopropionic acid
beta-alanine
3-Aminopropanoic acid
107-95-9
Beta Alanine
Abufene
H-beta-Ala-OH
beta-Aminopropionic acid
2-Carboxyethylamine
.beta.-Alanine
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives |
| Direct Parent | Beta amino acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 89.094 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 52.8 |
| Monoisotopic Mass | 89.048 |
| Exact Mass | 89.048 |
| XLogP | -3 |
| Formal Charge | 0 |
| Heavy Atom Count | 6 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7989 |
| Human Intestinal Absorption | HIA+ | 0.9004 |
| Caco-2 Permeability | Caco2- | 0.5996 |
| P-glycoprotein Substrate | Non-substrate | 0.7836 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9654 |
| Non-inhibitor | 0.9572 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8567 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6203 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8728 |
| CYP450 2D6 Substrate | Non-substrate | 0.7638 |
| CYP450 3A4 Substrate | Non-substrate | 0.7882 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9235 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9508 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9696 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9761 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9583 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9847 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9149 |
| Non-inhibitor | 0.9221 | |
| AMES Toxicity | Non AMES toxic | 0.8267 |
| Carcinogens | Non-carcinogens | 0.7603 |
| Fish Toxicity | Low FHMT | 0.9551 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 1.0000 |
| Honey Bee Toxicity | Low HBT | 0.5631 |
| Biodegradation | Ready biodegradable | 0.9607 |
| Acute Oral Toxicity | III | 0.5168 |
| Carcinogenicity (Three-class) | Non-required | 0.6419 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.1621 | LogS |
| Caco-2 Permeability | 0.6546 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.1302 | LD50, mol/kg |
| Fish Toxicity | 3.2456 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.2042 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Metabolite Profiling of a Zinc-Accumulating Rice Mutant. | J Agric Food Chem | 2017 May 10 | 28441480 |
| Muscle Carnosine Concentration with the Co-Ingestion of Carbohydrate withβ-alanine in Male Rats. | J Diet Suppl | 2017 Jul 4 | 27813677 |
| Metabolomic and physico-chemical approach unravel dynamic regulation of calciumin sweet cherry fruit physiology. | Plant Physiol Biochem | 2017 Jul | 28551418 |
| Effects of acute ingestion of a pre-workout dietary supplement with and withoutp-synephrine on resting energy expenditure, cognitive function and exerciseperformance. | J Int Soc Sports Nutr | 2017 Jan 12 | 28096758 |
| Use of sacrificial anode technology to mitigate non-enzymic Maillard browning. | Food Chem | 2017 Feb 15 | 27664627 |
| A urinary metabonomics analysis of long-term effect of acetochlor exposure on rats by ultra-performance liquid chromatography/mass spectrometry. | Pestic Biochem Physiol | 2016 Mar | 26969444 |
| Determination of β-N-oxalyl-L-α,β-diaminopropionic acid and homoarginine in Lathyrus sativus and Lathyrus cicera by capillary zone electrophoresis. | J Sci Food Agric | 2015 May | 24954190 |
| Neuromodulatory properties of fluorescent carbon dots: effect on exocytoticrelease, uptake and ambient level of glutamate and GABA in brain nerve terminals. | Int J Biochem Cell Biol | 2015 Feb | 25486182 |
| Effect of food preservatives on the hydration properties and taste behavior ofamino acids: a volumetric and viscometric approach. | Food Chem | 2015 Aug 15 | 25794759 |
| Cycads and their association with certain neurodegenerative diseases. | Neurologia | 2014 Nov-Dec | 23725821 |
| The effects of phytic acid on the Maillard reaction and the formation ofacrylamide. | Food Chem | 2013 Nov 1 | 23768320 |
| Perinatal taurine depletion increases susceptibility to adult sugar-inducedhypertension in rats. | Adv Exp Med Biol | 2009 | 19239143 |
| Increasing amino acid supply in pea embryos reveals specific interactions of Nand C metabolism, and highlights the importance of mitochondrial metabolism. | Plant J | 2008 Sep | 18494854 |
| Characterization and kinetic analysis of enzyme-substrate recognition by threerecombinant lactococcal PepVs. | Arch Biochem Biophys | 2006 Oct 15 | 16962986 |
| Mechanistic pathways of formation of acrylamide from different amino acids. | Adv Exp Med Biol | 2005 | 16438299 |
| Neurotoxic effects of alpha-fluoro-beta-alanine (FBAL) and fluoroacetic acid (FA) on dogs. | J Toxicol Sci | 2004 May | 15206584 |
| Electrochemical study of the Maillard reaction. | J Agric Food Chem | 2003 Mar 12 | 12617613 |
| Attenuation of bacterial lipopolysaccharide-induced hepatotoxicity by betaine or taurine in rats. | Food Chem Toxicol | 2002 Apr | 11893413 |
| Fumonisin B1 induces apoptosis in cultured human keratinocytes through sphinganine accumulation and ceramide depletion. | Int J Oncol | 1999 May | 10200332 |
| Volatile components formed from reaction of sugar and beta-alanine as a modelsystem of cookie processing. | Adv Exp Med Biol | 1998 | 9598205 |
Targets
- General Function:
- Neurotransmitter:sodium symporter activity
- Specific Function:
- Sodium-dependent GABA and taurine transporter. In presynaptic terminals, regulates GABA signaling termination through GABA uptake. May also be involved in beta-alanine transport.
- Gene Name:
- SLC6A13
- Uniprot ID:
- Q9NSD5
- Molecular Weight:
- 68008.205 Da
References
- Nakada K, Yoshikawa M, Ide S, Suemasa A, Kawamura S, Kobayashi T, Masuda E, Ito Y, Hayakawa W, Katayama T, Yamada S, Arisawa M, Minami M, Shuto S: Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: identification of an efficient lead for potent inhibitors of GABA transports. Bioorg Med Chem. 2013 Sep 1;21(17):4938-50. doi: 10.1016/j.bmc.2013.06.063. Epub 2013 Jul 8. [23886812 ]
- General Function:
- Neurotransmitter:sodium symporter activity
- Specific Function:
- Terminates the action of GABA by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A11
- Uniprot ID:
- P48066
- Molecular Weight:
- 70605.145 Da
References
- Nakada K, Yoshikawa M, Ide S, Suemasa A, Kawamura S, Kobayashi T, Masuda E, Ito Y, Hayakawa W, Katayama T, Yamada S, Arisawa M, Minami M, Shuto S: Cyclopropane-based conformational restriction of GABA by a stereochemical diversity-oriented strategy: identification of an efficient lead for potent inhibitors of GABA transports. Bioorg Med Chem. 2013 Sep 1;21(17):4938-50. doi: 10.1016/j.bmc.2013.06.063. Epub 2013 Jul 8. [23886812 ]
- General Function:
- L-proline transmembrane transporter activity
- Specific Function:
- Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
- Gene Name:
- SLC36A1
- Uniprot ID:
- Q7Z2H8
- Molecular Weight:
- 53075.045 Da
References
- Thondorf I, Voigt V, Schafer S, Gebauer S, Zebisch K, Laug L, Brandsch M: Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1). Bioorg Med Chem. 2011 Nov 1;19(21):6409-18. doi: 10.1016/j.bmc.2011.08.058. Epub 2011 Sep 5. [21955456 ]