ChemFOnt: Showing chemical card for (±)-erythro-Isoleucine (CFc000015004)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:04:00 UTC

Chemfont ID

CFc000015004

Molecule Identification

Common Name

(±)-erythro-Isoleucine

Definition

(±)-erythro-Isoleucine is a flavouring ingredient, dietary supplement, and a nutrient. Branched-chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAA denotes valine, isoleucine, and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats, and isoleucine to both. The different metabolism 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 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. BCAA are decreased in patients with liver disease such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia, or portacaval shunt. Aromatic amino acids (AAA)-tyrosine, tryptophan, and phenylalanine (as well as methionine) are increased in these conditions. Valine, in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. The BCAA are not without side effects. Leucine alone, for example, exacerbates pellagra and can cause psychosis in pellagra patients by increasing excretion of niacin in the urine. Leucine may lower brain serotonin and dopamine. The ratio of leucine to other BCAA is greatest in pork, where leucine is 7 to 8 g and the other BCAA together are only 3 to 4 g (http://www.dcnutrition.com).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+/-)-erythro-form	HMDB
(+/-)-isoleucine	HMDB
FEMA 3295	HMDB
Isoleucine	HMDB
2-Amino-3-methylpentanoic acid	MeSH

Chemical Formula

C₆H₁₃NO₂

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

IUPAC Name

2-amino-3-methylpentanoic acid

Traditional Name

L(+)-isoleucine

CAS Registry Number

443-79-8

SMILES

CCC(C)C(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)

InChI Key

AGPKZVBTJJNPAG-UHFFFAOYSA-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 chemical card for (±)-erythro-Isoleucine (CFc000015004)

MOL for CFc000015004 ((±)-erythro-Isoleucine)

3D MOL for CFc000015004 ((±)-erythro-Isoleucine)

3D SDF for CFc000015004 ((±)-erythro-Isoleucine)

3D-SDF for CFc000015004 ((±)-erythro-Isoleucine)

PDB for CFc000015004 ((±)-erythro-Isoleucine)

3D PDB for CFc000015004 ((±)-erythro-Isoleucine)

SMILES for CFc000015004 ((±)-erythro-Isoleucine)

INCHI for CFc000015004 ((±)-erythro-Isoleucine)

Structure for CFc000015004 ((±)-erythro-Isoleucine)

3D Structure for CFc000015004 ((±)-erythro-Isoleucine)