L-ALANINE
Relevant Data
Flavouring Substances Approved by European Union:
General Information
| Mainterm | L-ALANINE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 56-41-7 |
| Regnum |
172.320 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 5950 |
| IUPAC Name | (2S)-2-aminopropanoic acid |
| InChI | InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1 |
| InChI Key | QNAYBMKLOCPYGJ-REOHCLBHSA-N |
| Canonical SMILES | CC(C(=O)O)N |
| Molecular Formula | C3H7NO2 |
| Wikipedia | L-Alanine |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 89.094 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Complexity | 61.8 |
| CACTVS Substructure Key Fingerprint | A A A D c Y B C M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g A Q C A A A C C j B g A Q C C A B A A g A I A A C Q C A A A A A A A A A A A A I G A A A A C A A A A A A A A Q A A A E A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 63.3 |
| Monoisotopic Mass | 89.048 |
| Exact Mass | 89.048 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 6 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6314 |
| Human Intestinal Absorption | HIA+ | 0.9506 |
| Caco-2 Permeability | Caco2- | 0.8957 |
| P-glycoprotein Substrate | Non-substrate | 0.8222 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9919 |
| Non-inhibitor | 0.9952 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9644 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6664 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8125 |
| CYP450 2D6 Substrate | Non-substrate | 0.8851 |
| CYP450 3A4 Substrate | Non-substrate | 0.8204 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9460 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9645 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9748 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9797 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9384 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9938 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9891 |
| Non-inhibitor | 0.9841 | |
| AMES Toxicity | Non AMES toxic | 0.9339 |
| Carcinogens | Non-carcinogens | 0.6200 |
| Fish Toxicity | Low FHMT | 0.7134 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9839 |
| Honey Bee Toxicity | Low HBT | 0.5331 |
| Biodegradation | Ready biodegradable | 0.7662 |
| Acute Oral Toxicity | III | 0.5360 |
| Carcinogenicity (Three-class) | Non-required | 0.6749 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.7886 | LogS |
| Caco-2 Permeability | 0.4547 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.0339 | LD50, mol/kg |
| Fish Toxicity | 3.4484 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.5728 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | L-Alanine is a non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and the central nervous system. BCAAs are used as a source of energy for muscle cells. During prolonged exercise, BCAAs are released from skeletal muscles and their carbon backbones are used as fuel, while their nitrogen portion is used to form another amino acid, Alanine. Alanine is then converted to Glucose by the liver. This form of energy production is called the Alanine-Glucose cycle, and it plays a major role in maintaining the body's blood sugar balance. |
| Metabolism | None |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| 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 - Alpha amino acids and derivatives |
| Direct Parent | Alanine and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Alanine or derivatives - Alpha-amino acid - L-alpha-amino acid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organic oxygen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Primary aliphatic amine - Carbonyl group - Amine - Organopnictogen compound - Organic oxide - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as alanine and derivatives. These are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
From ClassyFire
Targets
- General Function:
- Pyridoxal phosphate binding
- Specific Function:
- Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate.
- Gene Name:
- GPT2
- Uniprot ID:
- Q8TD30
- Molecular Weight:
- 57903.11 Da
References
- Rajamohan F, Nelms L, Joslin DL, Lu B, Reagan WJ, Lawton M: cDNA cloning, expression, purification, distribution, and characterization of biologically active canine alanine aminotransferase-1. Protein Expr Purif. 2006 Jul;48(1):81-9. Epub 2006 Jan 30. [16495081 ]
- General Function:
- Trna binding
- Specific Function:
- Catalyzes the attachment of alanine to tRNA(Ala) in a two-step reaction: alanine is first activated by ATP to form Ala-AMP and then transferred to the acceptor end of tRNA(Ala). Also edits incorrectly charged tRNA(Ala) via its editing domain.
- Gene Name:
- AARS
- Uniprot ID:
- P49588
- Molecular Weight:
- 106809.525 Da
References
- Buechter DD, Schimmel P: Minor groove recognition of the critical acceptor helix base pair by an appended module of a class II tRNA synthetase. Biochemistry. 1995 May 9;34(18):6014-9. [7742303 ]
- General Function:
- Trna binding
- Specific Function:
- Catalyzes the attachment of alanine to tRNA(Ala) in a two-step reaction: alanine is first activated by ATP to form Ala-AMP and then transferred to the acceptor end of tRNA(Ala). Also edits incorrectly charged tRNA(Ala) via its editing domain.
- Gene Name:
- AARS2
- Uniprot ID:
- Q5JTZ9
- Molecular Weight:
- 107339.48 Da
References
- Buechter DD, Schimmel P: Minor groove recognition of the critical acceptor helix base pair by an appended module of a class II tRNA synthetase. Biochemistry. 1995 May 9;34(18):6014-9. [7742303 ]
- General Function:
- Sodium:dicarboxylate symporter activity
- Specific Function:
- Transporter for alanine, serine, cysteine, and threonine. Exhibits sodium dependence.
- Gene Name:
- SLC1A4
- Uniprot ID:
- P43007
- Molecular Weight:
- 55722.455 Da
References
- Wu Y, Shen D, Chen Z, Clayton S, Vadgama JV: Taxol induced apoptosis regulates amino acid transport in breast cancer cells. Apoptosis. 2007 Mar;12(3):593-612. Epub 2006 Dec 29. [17195090 ]
- General Function:
- Pyridoxal phosphate binding
- Specific Function:
- Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate. Participates in cellular nitrogen metabolism and also in liver gluconeogenesis starting with precursors transported from skeletal muscles (By similarity).
- Gene Name:
- GPT
- Uniprot ID:
- P24298
- Molecular Weight:
- 54636.415 Da
References
- Chen CH, Lee RP, Wu WT, Liao KW, Hsu N, Hsu BG: Fluvastatin ameliorates endotoxin induced multiple organ failure in conscious rats. Resuscitation. 2007 Jul;74(1):166-74. Epub 2007 Mar 13. [17353078 ]
- General Function:
- Transaminase activity
- Specific Function:
- Catalyzes the pyridoxal-phosphate-dependent breakdown of 5-phosphohydroxy-L-lysine, converting it to ammonia, inorganic phosphate and 2-aminoadipate semialdehyde.
- Gene Name:
- PHYKPL
- Uniprot ID:
- Q8IUZ5
- Molecular Weight:
- 49710.245 Da
References
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
- General Function:
- Pyridoxal phosphate binding
- Specific Function:
- Catalyzes the removal of elemental sulfur from cysteine to produce alanine. It supplies the inorganic sulfur for iron-sulfur (Fe-S) clusters. May be involved in the biosynthesis of molybdenum cofactor.
- Gene Name:
- NFS1
- Uniprot ID:
- Q9Y697
- Molecular Weight:
- 50195.21 Da
References
- Zeng J, Zhang Y, Liu Y, Zhang X, Xia L, Liu J, Qiu G: Expression, purification and characterization of a cysteine desulfurase, IscS, from Acidithiobacillus ferrooxidans. Biotechnol Lett. 2007 Dec;29(12):1983-90. Epub 2007 Jul 28. [17660944 ]
- General Function:
- Pyridoxal phosphate binding
- Specific Function:
- Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
- Gene Name:
- KYNU
- Uniprot ID:
- Q16719
- Molecular Weight:
- 52351.14 Da
References
- Lima S, Khristoforov R, Momany C, Phillips RS: Crystal structure of Homo sapiens kynureninase. Biochemistry. 2007 Mar 13;46(10):2735-44. Epub 2007 Feb 15. [17300176 ]
- General Function:
- Transaminase activity
- Gene Name:
- AGXT
- Uniprot ID:
- P21549
- Molecular Weight:
- 43009.535 Da
References
- Pirulli D, Puzzer D, Ferri L, Crovella S, Amoroso A, Ferrettini C, Marangella M, Mazzola G, Florian F: Molecular analysis of hyperoxaluria type 1 in Italian patients reveals eight new mutations in the alanine: glyoxylate aminotransferase gene. Hum Genet. 1999 Jun;104(6):523-5. [10453743 ]
- General Function:
- Pyridoxal phosphate binding
- Specific Function:
- Can metabolize asymmetric dimethylarginine (ADMA) via transamination to alpha-keto-delta-(NN-dimethylguanidino) valeric acid (DMGV). ADMA is a potent inhibitor of nitric-oxide (NO) synthase, and this activity provides mechanism through which the kidney regulates blood pressure.
- Gene Name:
- AGXT2
- Uniprot ID:
- Q9BYV1
- Molecular Weight:
- 57155.905 Da
References
- Okuno E, Ishikawa T, Kawai J, Kido R: Alanine:glyoxylate aminotransferase activities in liver of Suncus murinus (insectivora). Comp Biochem Physiol B. 1988;90(4):773-8. [2907870 ]
- 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 ]
- General Function:
- Succinate-semialdehyde dehydrogenase binding
- Specific Function:
- Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
- Gene Name:
- ABAT
- Uniprot ID:
- P80404
- Molecular Weight:
- 56438.405 Da
References
- Amadasi A, Bertoldi M, Contestabile R, Bettati S, Cellini B, di Salvo ML, Borri-Voltattorni C, Bossa F, Mozzarelli A: Pyridoxal 5'-phosphate enzymes as targets for therapeutic agents. Curr Med Chem. 2007;14(12):1291-324. [17504214 ]
- General Function:
- Toxin transporter activity
- Specific Function:
- Sodium-independent, high-affinity transport of small and large neutral amino acids such as alanine, serine, threonine, cysteine, phenylalanine, tyrosine, leucine, arginine and tryptophan, when associated with SLC3A2/4F2hc. Acts as an amino acid exchanger. Has higher affinity for L-phenylalanine than LAT1 but lower affinity for glutamine and serine. L-alanine is transported at physiological concentrations. Plays a role in basolateral (re)absorption of neutral amino acids. Involved in the uptake of methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes, and hence plays a role in metal ion homeostasis and toxicity. Involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L-nitrosocysteine (L-CNSO) across the transmembrane. Plays an essential role in the reabsorption of neutral amino acids from the epithelial cells to the bloodstream in the kidney.
- Gene Name:
- SLC7A8
- Uniprot ID:
- Q9UHI5
- Molecular Weight:
- 58381.12 Da
References
- Broer S, Broer A, Hansen JT, Bubb WA, Balcar VJ, Nasrallah FA, Garner B, Rae C: Alanine metabolism, transport, and cycling in the brain. J Neurochem. 2007 Sep;102(6):1758-70. Epub 2007 May 14. [17504263 ]
From T3DB