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Identification
NameL-Threonine
Accession NumberDB00156  (NUTR00057)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(2S,3R)-(-)-ThreonineNot AvailableNot Available
(2S)-threonineNot AvailableNot Available
2-Amino-3-hydroxybutyric acidNot AvailableNot Available
L-(-)-ThreonineNot AvailableNot Available
L-2-Amino-3-hydroxybutyric acidNot AvailableNot Available
L-alpha-amino-beta-hydroxybutyric acidNot AvailableNot Available
L-ThreoninNot AvailableNot Available
L-α-amino-β-hydroxybutyric acidNot AvailableNot Available
ThrNot AvailableNot Available
ThreonineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number72-19-5
WeightAverage: 119.1192
Monoisotopic: 119.058243159
Chemical FormulaC4H9NO3
InChI KeyAYFVYJQAPQTCCC-FGNFWGHYNA-N
InChI
InChI=1/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/s2
IUPAC Name
(2S,3R)-2-amino-3-hydroxybutanoic acid
SMILES
C[C@@H](O)[C@H](N)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Amino fatty acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationL-Threonine makes up collagen, elastin, and enamel protein. It aids proper fat metabolism in the liver, helps the digestive and intestinal tracts function more smoothly, and assists in metabolism and assimilation.
PharmacodynamicsL-Threonine is an essential amino acid that helps to maintain the proper protein balance in the body. It is important for the formation of collagen, elastin, and tooth enamel, and aids liver and lipotropic function when combined with aspartic acid and methionine.
Mechanism of actionL-Threonine is a precursor to the amino acids glycine and serine. It acts as a lipotropic in controlling fat build-up in the liver. May help combat mental illness and may be very useful in indigestion and intestinal malfunctions. Also, threonine prevents excessive liver fat. Nutrients are more readily absorbed when threonine is present.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.939
Blood Brain Barrier-0.6054
Caco-2 permeable-0.9009
P-glycoprotein substrateNon-substrate0.7827
P-glycoprotein inhibitor INon-inhibitor0.9851
P-glycoprotein inhibitor IINon-inhibitor0.9902
Renal organic cation transporterNon-inhibitor0.9634
CYP450 2C9 substrateNon-substrate0.8233
CYP450 2D6 substrateNon-substrate0.8832
CYP450 3A4 substrateNon-substrate0.8021
CYP450 1A2 substrateNon-inhibitor0.8694
CYP450 2C9 substrateNon-inhibitor0.9362
CYP450 2D6 substrateNon-inhibitor0.9529
CYP450 2C19 substrateNon-inhibitor0.9119
CYP450 3A4 substrateNon-inhibitor0.8683
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9806
Ames testNon AMES toxic0.9538
CarcinogenicityNon-carcinogens0.6811
BiodegradationReady biodegradable0.844
Rat acute toxicity1.2108 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9902
hERG inhibition (predictor II)Non-inhibitor0.9826
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
L-threonine crystal4.57USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point256 dec °CPhysProp
water solubility9.7E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-2.94HANSCH,C ET AL. (1995)
logS-0.09ADME Research, USCD
pKa5.60Not Available
Predicted Properties
PropertyValueSource
Water Solubility477.0 mg/mLALOGPS
logP-3ALOGPS
logP-3.5ChemAxon
logS0.6ALOGPS
pKa (Strongest Acidic)2.21ChemAxon
pKa (Strongest Basic)9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.46 m3·mol-1ChemAxon
Polarizability11.08 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.11 KB)
SpectraNot Available
References
Synthesis Reference

Masato Terasawa, Yukie Satoo, Hideaki Yukawa, “Method for production of l-threonine.” U.S. Patent US5019503, issued June, 1967.

US5019503
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (72.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Threonine synthase-like 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Threonine synthase-like 1 Q8IYQ7 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Threonine--tRNA ligase, cytoplasmic

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Threonine--tRNA ligase, cytoplasmic P26639 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Torres-Larios A, Sankaranarayanan R, Rees B, Dock-Bregeon AC, Moras D: Conformational movements and cooperativity upon amino acid, ATP and tRNA binding in threonyl-tRNA synthetase. J Mol Biol. 2003 Aug 1;331(1):201-11. Pubmed
  4. Ruan B, Bovee ML, Sacher M, Stathopoulos C, Poralla K, Francklyn CS, Soll D: A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases. J Biol Chem. 2005 Jan 7;280(1):571-7. Epub 2004 Oct 26. Pubmed
  5. Cusack S, Yaremchuk A, Krikliviy I, Tukalo M: tRNA(Pro) anticodon recognition by Thermus thermophilus prolyl-tRNA synthetase. Structure. 1998 Jan 15;6(1):101-8. Pubmed

3. Threonine--tRNA ligase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Threonine--tRNA ligase, mitochondrial Q9BW92 Details

References:

  1. Caillet J, Graffe M, Eyermann F, Romby P, Springer M: Mutations in residues involved in zinc binding in the catalytic site of Escherichia coli threonyl-tRNA synthetase confer a dominant lethal phenotype. J Bacteriol. 2007 Oct;189(19):6839-48. Epub 2007 Jul 20. Pubmed

Transporters

1. Monocarboxylate transporter 10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 10 Q8TF71 Details

References:

  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 13:37