L-Alanine
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Basic Info
| Common Name | L-Alanine(F05339) |
| 2D Structure | |
| Description | Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. 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. |
| FRCD ID | F05339 |
| CAS Number | 56-41-7 |
| PubChem CID | 5950 |
| Formula | C3H7NO2 |
| IUPAC Name | (2S)-2-aminopropanoic acid |
| InChI Key | QNAYBMKLOCPYGJ-REOHCLBHSA-N |
| InChI | InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1 |
| Canonical SMILES | CC(C(=O)O)N |
| Isomeric SMILES | C[C@@H](C(=O)O)N |
| Wikipedia | L-Alanine |
| Synonyms |
(S)-2-Aminopropanoic acid
L-alanine
56-41-7
alanine
L-alpha-alanine
(S)-Alanine
L-2-Aminopropionic acid
(2S)-2-Aminopropanoic acid
H-Ala-OH
L-(+)-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 - 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. |
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 |
| Monoisotopic Mass | 89.048 |
| Exact Mass | 89.048 |
| XLogP | -3 |
| 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 |
ADMET
| 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 |
| 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 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Toxicity of flavor enhancers to the oriental fruit fly, Bactrocera dorsalis (Hendel) (Diptera: Tephritidae). | Ecotoxicology | 2018 Jul | 29644544 |
| Cyanobacterial Neurotoxins: Their Occurrence and Mechanisms of Toxicity. | Neurotox Res | 2018 Jan | 28585115 |
| Analysis of Neurotoxic Amino Acids from Marine Waters, Microbial Mats, and Seafood Destined for Human Consumption in the Arabian Gulf. | Neurotox Res | 2018 Jan | 28766269 |
| Creating a Simian Model of Guam ALS/PDC Which Reflects Chamorro Lifetime BMAA Exposures. | Neurotox Res | 2018 Jan | 28478528 |
| Effects of flavor enhancers on the survival and behavior of the red imported fire ant, Solenopsis invicta (Hymenoptera: Formicidae). | Environ Sci Pollut Res Int | 2018 Aug | 29796890 |
| Structural characterization of melanoidin formed from d-glucose and l-alanine at different temperatures applying FTIR, NMR, EPR, and MALDI-ToF-MS. | Food Chem | 2018 Apr 15 | 29287438 |
| Impact of temperature, nutrients, pH and cold storage on the germination, growth and resistance of Bacillus cereus spores in egg white. | Food Res Int | 2018 Apr | 29579940 |
| Detection of the suspected neurotoxin β-methylamino-l-alanine (BMAA) in cyanobacterial blooms from multiple water bodies in Eastern Australia. | Harmful Algae | 2018 Apr | 29724339 |
| Protein association of β-N-methylamino-L-alanine in Triticum aestivum via irrigation. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018 Apr | 29324084 |
| Genetic Environment of cry1 Genes Indicates Their Common Origin. | Genome Biol Evol | 2017 Sep 1 | 29617829 |
| Formation of Reactive Intermediates, Color, and Antioxidant Activity in theMaillard Reaction of Maltose in Comparison to d-Glucose. | J Agric Food Chem | 2017 Oct 11 | 28880081 |
| Influence of l-pyroglutamic acid on the color formation process of non-enzymatic browning reactions. | Food Chem | 2017 Oct 1 | 28490097 |
| Dietary exposure and neurotoxicity of the environmental free and bound toxin β-N-methylamino-l-alanine. | Food Res Int | 2017 Oct | 28873667 |
| Spore Heat Activation Requirements and Germination Responses Correlate withSequences of Germinant Receptors and with the Presence of a Specific spoVA2mobOperon in Foodborne Strains of Bacillus subtilis. | Appl Environ Microbiol | 2017 Mar 17 | 28130296 |
| Characterization of three autolysins with activity against cereulide-producing Bacillus isolates in food matrices. | Int J Food Microbiol | 2017 Jan 16 | 27835772 |
| Detection of Cyanotoxins in Algae Dietary Supplements. | Toxins (Basel) | 2017 Feb 25 | 28245621 |
| Cellular and Molecular Aspects of the β-N-Methylamino-l-alanine (BMAA) Mode of Action within the Neurodegenerative Pathway: Facts and Controversy. | Toxins (Basel) | 2017 Dec 22 | 29271898 |
| Determination of neurotoxic agents as markers of common vetch adulteration in lentil by LC-MS/MS. | Food Chem | 2017 Apr 15 | 27979192 |
| Neonatal Citrulline Supplementation and Later Exposure to a High Fructose Diet inRats Born with a Low Birth Weight: A Preliminary Report. | Nutrients | 2017 Apr 11 | 28398243 |
| Transfer of developmental neurotoxin β-N-methylamino-l-alanine (BMAA) via milk to nursed offspring: Studies by mass spectrometry and image analysis. | Toxicol Lett | 2016 Sep 6 | 27320960 |
Targets
- 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
- Zhang Z, Papageorgiou G, Corrie JE, Grewer C: Pre-steady-state currents in neutral amino acid transporters induced by photolysis of a new caged alanine derivative. Biochemistry. 2007 Mar 27;46(12):3872-80. Epub 2007 Feb 21. [17311416 ]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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
- Miyashita Y, Dolferus R, Ismond KP, Good AG: Alanine aminotransferase catalyses the breakdown of alanine after hypoxia in Arabidopsis thaliana. Plant J. 2007 Mar;49(6):1108-21. Epub 2007 Feb 22. [17319845 ]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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
- You D, Wang L, Yao F, Zhou X, Deng Z: A novel DNA modification by sulfur: DndA is a NifS-like cysteine desulfurase capable of assembling DndC as an iron-sulfur cluster protein in Streptomyces lividans. Biochemistry. 2007 May 22;46(20):6126-33. Epub 2007 May 1. [17469805 ]
- 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
- Christensen M, Duno M, Lund AM, Skovby F, Christensen E: Xanthurenic aciduria due to a mutation in KYNU encoding kynureninase. J Inherit Metab Dis. 2007 Apr;30(2):248-55. Epub 2007 Mar 1. [17334708 ]
- 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 ]