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Details

Stereochemistry RACEMIC
Molecular Formula C4H9NO3
Molecular Weight 119.1192
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THREONINE, DL-

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula C4H9NO3
Molecular Weight 119.1192
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

L-threonine is an essential amino acid. Threonine is a precursor of glycine. The biochemical studies on rats proved that glycine is synthesized from threonine (through threonine dehydrogenase pathway). Threonine dehydrogenase is the key enzyme in mammals like pigs, cat, and rats for degradation of 80% threonine. In adult humans, degradation of 7–11% of threonine is done by threonine dehydrogenase. The human L-threonine 3-dehydrogenase gene (GeneID: 157739, UniProtKB: Q8IZJ6 (TDH_HUMAN)) is an expressed pseudogene having lost the splice acceptor site preceding exon 6 and codon arginine-214 (CGA) is mutated to a stop codon (TGA). A few trials demonstrated that oral L-threonine may alleviate clinical signs of amyotrophic lateral sclerosis and spasticity in humans. L-Threonine has recently been brought into agricultural industry for balancing the livestock feed.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FREAMINE III 10%
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
200 μM
15 mg/kg single, intravenous
THREONINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
300 μg × h/mL
15 mg/kg single, intravenous
THREONINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
15 mg/kg single, intravenous
THREONINE plasma
Homo sapiens

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
L-threonine (4 g daily) with pyridoxal phosphate (160 mg daily) for six months in patients with amyotrophic lateral sclerosis. Threonine supplementation (500 mg/day) was given to 6 patients with genetic spasticity syndromes for a period of 12 months, followed by a 4-month observation period without medication. Oral L-threonine at 6 g/day in patients with spinal spasticity.
Route of Administration: Oral
In Vitro Use Guide
20 mM L-Threonine increases heat shock protein (HSP)70 and HSP25 expression and protects intestinal epithelial cells from heat stress injury
Substance Class Chemical
Record UNII
TFM6DU5S6A
Record Status Validated (UNII)
Record Version