You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (17)transporters (4) Show 21 proteins XML

enzymes (17)transporters (4) Show 21 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-05-30 20:56:03 UTC

HMDB ID

HMDB0000161

Secondary Accession Numbers

HMDB00161

Metabolite Identification

Common Name

L-Alanine

Description

Alanine (Ala), also known as L-alanine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Alanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. In humans, alanine is a non-essential amino acid that can be easily made in the body from either the conversion of pyruvate or the breakdown of the dipeptides carnosine and anserine. Alanine can be also synthesized from branched chain amino acids such as valine, leucine, and isoleucine. Alanine is produced by reductive amination of pyruvate through a two-step process. In the first step, alpha-ketoglutarate, ammonia and NADH are converted by the enzyme known glutamate dehydrogenase to glutamate, NAD+ and water. In the second step, the amino group of the newly-formed glutamate is transferred to pyruvate by an aminotransferase enzyme, regenerating the alpha-ketoglutarate, and converting the pyruvate to alanine. The net result is that pyruvate and ammonia are converted to alanine. In mammals, alanine plays a key role in glucose-alanine cycle between tissues and liver. In muscle and other tissues that degrade amino acids for fuel, amino groups are collected in the form of glutamate by transamination. Glutamate can then transfer its amino group to pyruvate, a product of muscle glycolysis, through the action of alanine aminotransferase, forming alanine and alpha-ketoglutarate. The alanine enters the bloodstream and is transported to the liver. The alanine aminotransferase reaction takes place in reverse in the liver, where the regenerated pyruvate is used in gluconeogenesis, forming glucose which returns to the muscles through the circulation system. Alanine 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 a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine is reduced in both severe hypoglycemia and the ketosis of diabetes. Alanine 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 (http://www.dcnutrition.com/AminoAcids/).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-2-Aminopropanoic acid	ChEBI
(S)-2-Aminopropanoic acid	ChEBI
(S)-Alanine	ChEBI
A	ChEBI
Ala	ChEBI
ALANINE	ChEBI
L-2-Aminopropionic acid	ChEBI
L-Alanin	ChEBI
L-alpha-Alanine	ChEBI
(2S)-2-Aminopropanoate	Generator
(S)-2-Aminopropanoate	Generator
L-2-Aminopropionate	Generator
L-a-Alanine	Generator
L-Α-alanine	Generator
(S)-(+)-Alanine	HMDB
(S)-2-Amino-propanoate	HMDB
(S)-2-Amino-propanoic acid	HMDB
2-Aminopropanoate	HMDB
2-Aminopropanoic acid	HMDB
2-Aminopropionate	HMDB
2-Aminopropionic acid	HMDB
2-Ammoniopropanoate	HMDB
2-Ammoniopropanoic acid	HMDB
a-Alanine	HMDB
a-Aminopropionate	HMDB
a-Aminopropionic acid	HMDB
alpha-Alanine	HMDB
alpha-Aminopropanoate	HMDB
alpha-Aminopropanoic acid	HMDB
alpha-Aminopropionate	HMDB
alpha-Aminopropionic acid	HMDB
L-(+)-Alanine	HMDB
L-2-Aminopropanoate	HMDB
L-2-Aminopropanoic acid	HMDB
L-a-Aminopropionate	HMDB
L-a-Aminopropionic acid	HMDB
L-alpha-Aminopropionate	HMDB
L-alpha-Aminopropionic acid	HMDB
Abufène	HMDB
Alanine doms-adrian brand	HMDB
Alanine, L-isomer	HMDB
Doms-adrian brand OF alanine	HMDB
Doms adrian brand OF alanine	HMDB
L-Isomer alanine	HMDB
Alanine, L isomer	HMDB
L Alanine	HMDB

Chemical Formula

C₃H₇NO₂

Average Molecular Weight

89.0932

Monoisotopic Molecular Weight

89.047678473

IUPAC Name

(2S)-2-aminopropanoic acid

Traditional Name

L-alanine

CAS Registry Number

56-41-7

SMILES

C[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1

InChI Key

QNAYBMKLOCPYGJ-REOHCLBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives 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.

Showing metabocard for L-Alanine (HMDB0000161)

MOL for HMDB0000161 (L-Alanine)

3D MOL for HMDB0000161 (L-Alanine)

3D SDF for HMDB0000161 (L-Alanine)

3D-SDF for HMDB0000161 (L-Alanine)

PDB for HMDB0000161 (L-Alanine)

3D PDB for HMDB0000161 (L-Alanine)

SMILES for HMDB0000161 (L-Alanine)

INCHI for HMDB0000161 (L-Alanine)

Structure for HMDB0000161 (L-Alanine)

3D Structure for HMDB0000161 (L-Alanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra