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L-isoleucine

File:L-Isoleucin_-_L-Isoleucine.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ484940· pop 63· linked from 781 articles

L-isoleucine

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Also known as L-Ile, (2S,3S)-2-Amino-3-methylpentanoic acid, 2-Amino-3-methylvaleric acid, alpha-amino-beta-methylvaleric acid, I, Ile, Isoleucine, α-amino-β-methylvaleric acid

thumb|Isoleucine ball and stick model spinning Isoleucine (symbol Ile or I) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a hydrocarbon side chain with a branch (a central carbon atom bound to three other carbon atoms). It is classified as a non-polar, uncharged (at physiological pH), branched-chain, aliphatic amino acid. It is essential in humans, meaning the body cannot synthesi

OverviewAI-generated

L-isoleucine is a chemical compound with the IUPAC name (2S,3S)-2-amino-3-methylpentanoic acid. Its chemical formula is C₆H₁₃NO₂, and it has a mass of 131.095. The compound is characterized by a pKa of 9.758 and a solubility of 0.09.

Structural data indicates that L-isoleucine has a charge of 0. It possesses two hydrogen bond donors and three hydrogen bond acceptors. The topological polar surface area is 63.3, and the xlogp value is -1.7. The isomeric SMILES notation for the molecule is CC[C@H](C)[C@H](N)C(O)=O.

Synthesized by Vinony from 21 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula
C6H13NO2
Molecular weight
131.17 g/mol
IUPAC name
(2S,3S)-2-amino-3-methylpentanoic acid
SMILES
CC[C@H](C)[C@@H](C(=O)O)N
InChIKey
AGPKZVBTJJNPAG-WHFBIAKZSA-N
XLogP
-1.7
Polar surface area
63.3 Ų
H-bond donors
2
H-bond acceptors
3
Formal charge
0

via PubChem

Research

19,589 papers

via PubMed

Wikidata facts

Subclass of
proteinogenic amino acid
Part of
egg as food
Has part
carbon
Mass
131.095
Has use
medication
Show 9 more facts
Commons category
Isoleucine
found in taxon
Caenorhabditis elegans
chemical formula
C₆H₁₃NO₂
canonical SMILES
CCC(C)C(C(=O)O)N
pKa
9.758
isomeric SMILES
CC[C@H](C)[C@H](N)C(O)=O
NCI Thesaurus ID
C29598
solubility
0.09
has characteristic
bitterness
Sources (3)

via Wikidata · CC0

~5 min read

Encyclopedic overview

11 sections
Contents
  • Metabolism
  • Biosynthesis
  • Catabolism
  • Metabolic diseases
  • Insulin resistance
  • Functions and requirement
  • Synthesis
  • Discovery
  • See also
  • References
  • External links

thumb|Isoleucine ball and stick model spinning Isoleucine (symbol Ile or I) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a hydrocarbon side chain with a branch (a central carbon atom bound to three other carbon atoms). It is classified as a non-polar, uncharged (at physiological pH), branched-chain, aliphatic amino acid. It is essential in humans, meaning the body cannot synthesize it. Essential amino acids are necessary in the human diet. In plants isoleucine can be synthesized from threonine and methionine. In plants and bacteria, isoleucine is synthesized from a pyruvate employing leucine biosynthesis enzymes. It is encoded by the codons AUU, AUC, and AUA.

== Metabolism ==

Excerpted from Wikipedia’s “L-isoleucine” article, available under the CC BY-SA 4.0 licence.

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