FComEx: L-Threonine (PC000112)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:32 UTC

Update date

2017-01-19 02:36:13 UTC

FoodComEx ID

PC000112

FoodDB Record

FDB011999

Chemical Information

Name

L-Threonine

Description

Threonine, abbreviated Thr or T, is an essential amino acid in humans. It has a side chain containing a hydroxyl group, making it a polar, uncharged amino acid Threonine is catabolized in mammals largely (70-80%) by threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate (which forms glycine and acetyl CoA), and much less by threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia. It is highly concentrated in meat products, cottage cheese and wheat germ. It is abundant in human plasma, particularly in newborns. The threonine content of most infant formulas currently on the market is approximately 20% higher than the threonine concentration in human milk. Premature infants fed these formulas have twice the plasma threonine concentrations of breast-fed infants. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided (PMID 9853925). Threonine is an immunostimulant which promotes the growth of thymus gland and probably promotes cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 g per day. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals.

CAS Number

72-19-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S,3R)-(-)-Threonine	biospider
(2S,3R)-2-Amino-3-hydroxybutanoic acid	biospider
(2S,3R)-2-Amino-3-hydroxybutyrate	biospider
(2S,3R)-2-Amino-3-hydroxybutyric acid	biospider
(2S)-Threonine	biospider
(R-(R,s))-2-amino-3-hydroxybutanoate	HMDB
(R-(R,s))-2-amino-3-hydroxybutanoic acid	HMDB
(S)-Threonine	biospider
[R-(R,s)]-2-amino-3-hydroxy-butanoate	HMDB
[R-(R,s)]-2-amino-3-hydroxy-butanoic acid	HMDB
[R-(R,s)]-2-amino-3-hydroxybutanoate	HMDB
[R-(R,s)]-2-amino-3-hydroxybutanoic acid	HMDB
2-amino-3-Hydroxybutanoate	HMDB
2-amino-3-Hydroxybutanoic acid	HMDB
2-amino-3-Hydroxybutyrate	Generator
2-amino-3-Hydroxybutyric acid	ChEBI
L-(-)-Threonine	biospider
L-2-Amino-3-hydroxybutyrate	biospider
L-2-Amino-3-hydroxybutyric acid	biospider
L-a-amino-b-Hydroxybutyrate	Generator
L-a-amino-b-Hydroxybutyric acid	Generator
L-alpha-Amino-beta-hydroxybutyrate	biospider
L-alpha-Amino-beta-hydroxybutyric acid	biospider
L-Thr	biospider
L-Threonin	ChEBI
L-Threonine (9CI)	biospider
L-α-amino-β-hydroxybutyrate	Generator
L-α-amino-β-hydroxybutyric acid	Generator
T	ChEBI
Thr	ChEBI
Threonin	HMDB
THREONINE	ChEBI

Chemical Formula

C4H9NO3

IUPAC name

(2S,3R)-2-amino-3-hydroxybutanoic acid

InChI Identifier

InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1

InChI Key

AYFVYJQAPQTCCC-GBXIJSLDSA-N

Isomeric SMILES

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

Average Molecular Weight

119.1192

Monoisotopic Molecular Weight

119.058243159

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Beta-hydroxy acid
Short-chain hydroxy acid
Hydroxy acid
Fatty acid
Amino acid
Secondary alcohol
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:16857 )
proteinogenic amino acid (CHEBI:16857 )
L-alpha-amino acid (CHEBI:16857 )
threonine (CHEBI:16857 )
Common amino acids (C00188 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-2.94	HANSCH,C ET AL. (1995)
Experimental Water Solubility	97 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 251-253° dec.	DFC

Foods of Origin