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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6)transporters (1) Show 7 proteins XML

enzymes (6)transporters (1) Show 7 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-07-07 20:53:57 UTC

HMDB ID

HMDB0000172

Secondary Accession Numbers

HMDB00172

Metabolite Identification

Common Name

Isoleucine

Description

Isoleucine (Ile) or L-isoleucine 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-isolecuine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Isoleucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Isoleucine is an essential amino acid in humans, meaning the body cannot synthesize it and that it must be obtained from the diet. In plants and microorganisms, isoleucine is synthesized starting from pyruvate and alpha-ketobutyrate. Isoleucine is classified as a branched chain amino acid (BCAA). BCAAs include three amino acids: isoleucine, leucine and valine. They are alpha amino acids whose carbon structure is marked by a beta branch point. Despite their structural similarities, BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. Isoleucine is catabolized via with alpha-ketoglutarate where upon it is oxidized and split into propionyl-CoA and acetyl-CoA. Propionyl-CoA is converted into succinyl-CoA, a TCA cycle intermediate which can be converted into oxaloacetate for gluconeogenesis (hence glucogenic). The acetyl-CoA can be fed into the TCA cycle by condensing with oxaloacetate to form citrate or used in the synthesis of ketone bodies or fatty acids. The different metabolism of BCAAs accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine are required respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAAs are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia. An inability to break down isoleucine, along with other amino acids, is associated with maple syrup urine disease (MSUD) (PMID: 34125801 ). Isoleucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of isoleucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287 ). Mice fed an isoleucine deprivation diet for one day have improved insulin sensitivity, and feeding of an isoleucine deprivation diet for one week significantly decreases blood glucose levels (PMID: 24684822 ).

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,3S)-2-Amino-3-methylpentanoic acid	ChEBI
2-Amino-3-methylvaleric acid	ChEBI
alpha-Amino-beta-methylvaleric acid	ChEBI
I	ChEBI
Ile	ChEBI
ISOLEUCINE	ChEBI
(2S,3S)-2-Amino-3-methylpentanoate	Generator
2-Amino-3-methylvalerate	Generator
a-Amino-b-methylvalerate	Generator
a-Amino-b-methylvaleric acid	Generator
alpha-Amino-beta-methylvalerate	Generator
Α-amino-β-methylvalerate	Generator
Α-amino-β-methylvaleric acid	Generator
(2S,3S)-2-Amino-3-methyl-pentanoate	HMDB
(2S,3S)-2-Amino-3-methyl-pentanoic acid	HMDB
(2S,3S)-a-Amino-b-methyl-N-valerate	HMDB
(2S,3S)-a-Amino-b-methyl-N-valeric acid	HMDB
(2S,3S)-a-Amino-b-methylvalerate	HMDB
(2S,3S)-a-Amino-b-methylvaleric acid	HMDB
(2S,3S)-Alph-amino-beta-methylvalerate	HMDB
(2S,3S)-Alph-amino-beta-methylvaleric acid	HMDB
(2S,3S)-alpha-Amino-beta-merthyl-N-valerate	HMDB
(2S,3S)-alpha-Amino-beta-merthyl-N-valeric acid	HMDB
(2S,3S)-alpha-Amino-beta-merthylvalerate	HMDB
(2S,3S)-alpha-Amino-beta-merthylvaleric acid	HMDB
(2S,3S)-alpha-Amino-beta-methyl-N-valerate	HMDB
(2S,3S)-alpha-Amino-beta-methyl-N-valeric acid	HMDB
(2S,3S)-alpha-Amino-beta-methylvalerate	HMDB
(2S,3S)-alpha-Amino-beta-methylvaleric acid	HMDB
(S)-Isoleucine	HMDB
(S,S)-Isoleucine	HMDB
2-Amino-3-methylpentanoate	HMDB
2-Amino-3-methylpentanoic acid	HMDB
2S,3S-Isoleucine	HMDB
Erythro-L-isoleucine	HMDB
Iso-leucine	HMDB
L-(+)-Isoleucine	HMDB
L-Ile	HMDB
[S-(R,r)]-2-amino-3-methylpentanoate	HMDB
[S-(R,r)]-2-amino-3-methylpentanoic acid	HMDB
Isoleucine, L-isomer	HMDB
Alloisoleucine	HMDB
Isoleucine, L isomer	HMDB
L-Isomer isoleucine	HMDB
2S-Amino-3S-methylpentanoate	HMDB
L-Isoleucine	KEGG

Chemical Formula

C₆H₁₃NO₂

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

IUPAC Name

(2S,3S)-2-amino-3-methylpentanoic acid

Traditional Name

L-isoleucine

CAS Registry Number

73-32-5

SMILES

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

InChI Identifier

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1

InChI Key

AGPKZVBTJJNPAG-WHFBIAKZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Showing metabocard for Isoleucine (HMDB0000172)

MOL for HMDB0000172 (Isoleucine)

3D MOL for HMDB0000172 (Isoleucine)

3D SDF for HMDB0000172 (Isoleucine)

3D-SDF for HMDB0000172 (Isoleucine)

PDB for HMDB0000172 (Isoleucine)

3D PDB for HMDB0000172 (Isoleucine)

SMILES for HMDB0000172 (Isoleucine)

INCHI for HMDB0000172 (Isoleucine)

Structure for HMDB0000172 (Isoleucine)

3D Structure for HMDB0000172 (Isoleucine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra