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
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
| Molecular Formula | C4H9NO3 |
| Molecular Weight | 119.1192 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8296531 | https://www.ncbi.nlm.nih.gov/pubmed/1905383 | https://www.ncbi.nlm.nih.gov/pubmed/12523390
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8296531 | https://www.ncbi.nlm.nih.gov/pubmed/1905383 | https://www.ncbi.nlm.nih.gov/pubmed/12523390
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: EC 1.1.1.103 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | FREAMINE III 10% Approved UseParenteral nutrition with 8.5% FreAmine® III (Amino Acid Injection) with Electrolytes is
indicated to prevent nitrogen loss or treat negative nitrogen balance in adults and pediatric
patients, where (1) the alimentary tract, by the oral, gastrostomy, or jejunostomy route, cannot or
should not be used, or adequate protein intake is not feasible by these routes; (2) gastrointestinal
absorption of protein is impaired; or (3) protein requirements are substantially increased as with
extensive burns. Dosage, route of administration, and concomitant infusion of non-protein
calories are dependent on various factors, such as nutritional metabolic status of the patient, anticipated duration of parenteral nutritional support, and vein tolerance Launch Date1971 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
200 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/685879/ |
15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
THREONINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
300 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/685879/ |
15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
THREONINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/685879/ |
15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
THREONINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The first constant-domain (CH1) exon of human IGHG2 is polymorphic and in strong linkage disequilibrium with the CH2 exon polymorphism encoding the G2m(n+) allotype in Caucasians. | 2001 |
|
| Deficiency of Pten accelerates mammary oncogenesis in MMTV-Wnt-1 transgenic mice. | 2001 |
|
| Biosynthesis of vitamin B6 and structurally related derivatives. | 2001 |
|
| Novel mutations in the GALK1 gene in patients with galactokinase deficiency. | 2001 |
|
| Direct and differential interaction of beta-arrestins with the intracellular domains of different opioid receptors. | 2001 Apr |
|
| Phosphoserine/threonine-binding domains. | 2001 Apr |
|
| Mutation at codon 130 in hepatitis B virus (HBV) core region increases markedly during acute exacerbation of hepatitis in chronic HBV carriers. | 2001 Feb |
|
| Tyrosine phosphorylation of p120(ctn) in v-Src transfected L cells depends on its association with E-cadherin and reduces adhesion activity. | 2001 Feb |
|
| Molecular interactions between the specialist herbivore Manduca sexta (Lepidoptera, Sphingidae) and its natural host Nicotiana attenuata. II. Accumulation of plant mRNAs in response to insect-derived cues. | 2001 Feb |
|
| Database analysis of O-glycosylation sites in proteins. | 2001 Feb |
|
| The codon 17 polymorphism of the CTLA4 gene in type 2 diabetes mellitus. | 2001 Feb |
|
| Biosynthesis of threonine from homoserine by mixed rumen microorganisms: an in vitro study. | 2001 Feb |
|
| LIM-kinase 2 induces formation of stress fibres, focal adhesions and membrane blebs, dependent on its activation by Rho-associated kinase-catalysed phosphorylation at threonine-505. | 2001 Feb 15 |
|
| Threonine 180 is required for G-protein-coupled receptor kinase 3- and beta-arrestin 2-mediated desensitization of the mu-opioid receptor in Xenopus oocytes. | 2001 Feb 16 |
|
| Ceramide induces the dephosphorylation and inhibition of constitutively activated Akt in PTEN negative U87mg cells. | 2001 Feb 2 |
|
| p38 Kinase-dependent MAPKAPK-2 activation functions as 3-phosphoinositide-dependent kinase-2 for Akt in human neutrophils. | 2001 Feb 2 |
|
| The C terminus of mammalian phospholipase D is required for catalytic activity. | 2001 Feb 23 |
|
| The kinetic mechanism of the dual phosphorylation of the ATF2 transcription factor by p38 mitogen-activated protein (MAP) kinase alpha. Implications for signal/response profiles of MAP kinase pathways. | 2001 Feb 23 |
|
| Inhibition of PP-2A upregulates CaMKII in rat forebrain and induces hyperphosphorylation of tau at Ser 262/356. | 2001 Feb 9 |
|
| Thr226 is a key residue for bioluminescence spectra determination in beetle luciferases. | 2001 Feb 9 |
|
| Near-infrared reflectance spectroscopy enables the fast and accurate prediction of the essential amino acid contents in soy, rapeseed meal, sunflower meal, peas, fishmeal, meat meal products, and poultry meal. | 2001 Jan |
|
| Identification of tyrosine-phosphorylated proteins associated with the nuclear envelope. | 2001 Jan |
|
| Serine/threonine phosphorylation of IRS-1 triggers its degradation: possible regulation by tyrosine phosphorylation. | 2001 Jan |
|
| An in vivo study of ovine placental transport of essential amino acids. | 2001 Jan |
|
| Utilizing the peptidyl-prolyl cis-trans isomerase pin1 as a probe of its phosphorylated target proteins. Examples of binding to nuclear proteins in a human kidney cell line and to tau in Alzheimer's diseased brain. | 2001 Jan |
|
| Citrullinemia type II in a 64-year-old man with fluctuating serum citrulline levels. | 2001 Jan 1 |
|
| FMN is covalently attached to a threonine residue in the NqrB and NqrC subunits of Na(+)-translocating NADH-quinone reductase from Vibrio alginolyticus. | 2001 Jan 12 |
|
| Differential effects of the allosteric enhancer (2-amino-4,5-dimethyl-trienyl)[3-trifluoromethyl) phenyl]methanone (PD81,723) on agonist and antagonist binding and function at the human wild-type and a mutant (T277A) adenosine A1 receptor. | 2001 Jan 15 |
|
| Serotonin activates S6 kinase in a rapamycin-sensitive manner in Aplysia synaptosomes. | 2001 Jan 15 |
|
| Follicle-stimulating-hormone receptor and twinning. | 2001 Jan 20 |
|
| A molecular marker for chloroquine-resistant falciparum malaria. | 2001 Jan 25 |
|
| Protein control of the redox potential of the primary quinone acceptor in reactioncCenters from Rhodobacter sphaeroides. | 2001 Jan 30 |
|
| Electrical activity regulates AChR gene expression via JNK, PKCzeta and Sp1 in skeletal chick muscle. | 2001 Jan 5 |
|
| Identification of distinct signaling pathways leading to the phosphorylation of interferon regulatory factor 3. | 2001 Jan 5 |
|
| Studies on feeding peanut meal as a protein source for broiler chickens. | 2001 Mar |
|
| Cytoplasmic localization of p21Cip1/WAF1 by Akt-induced phosphorylation in HER-2/neu-overexpressing cells. | 2001 Mar |
|
| Isolation and characterisation of genomic and cDNA clones coding for a serine-, alanine-, and proline-rich protein of Trypanosoma cruzi. | 2001 Mar |
|
| Three-dimensional structure of human follicle-stimulating hormone. | 2001 Mar |
|
| Topology and structure of the C1q-binding site on C-reactive protein. | 2001 Mar 15 |
|
| Hydrophobic analogues of the winter flounder 'antifreeze' protein. | 2001 Mar 2 |
|
| Mass spectrometric resolution of reversible protein phosphorylation in photosynthetic membranes of Arabidopsis thaliana. | 2001 Mar 9 |
|
| The two major plant plasma membrane H+-ATPases display different regulatory properties. | 2001 Mar 9 |
|
| Identification of the bile acid-binding site of the ileal lipid-binding protein by photoaffinity labeling, matrix-assisted laser desorption ionization-mass spectrometry, and NMR structure. | 2001 Mar 9 |
|
| Phosphorylation-dependent conformation and proteolytic stability of c-Myb. | 2001 Mar-Apr |
|
| Synthesis of bisaminoacylated pdCpAs and tandemly activated transfer RNAs. | 2007 Jul 1 |
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 05:59:33 GMT 2023
by
admin
on
Sat Dec 16 05:59:33 GMT 2023
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| Record UNII |
TFM6DU5S6A
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
ENANTIOMER -> RACEMATE |
