You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot 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
Mass Specshow(8.11 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsAmino Fatty Acids; Beta Hydroxy Acids and Derivatives; Secondary Alcohols; Enolates; Polyamines; Carboxylic Acids; Monoalkylamines
Substituentsbeta-hydroxy acid; hydroxy acid; secondary alcohol; enolate; polyamine; carboxylic acid; amine; organonitrogen compound; primary aliphatic amine; alcohol; primary amine
Classification descriptionThis compound belongs to the alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
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
Pathways
PathwayCategorySMPDB ID
Threonine and 2-Oxobutanoate DegradationMetabolicSMP00452
Azithromycin Action PathwayDrug actionSMP00247
Gentamicin Action PathwayDrug actionSMP00254
Streptomycin Action PathwayDrug actionSMP00259
Chloramphenicol Action PathwayDrug actionSMP00729
Clomocycline Action PathwayDrug actionSMP00262
Clarithromycin Action PathwayDrug actionSMP00248
Kanamycin Action PathwayDrug actionSMP00255
Demeclocycline Action PathwayDrug actionSMP00290
Minocycline Action PathwayDrug actionSMP00292
Troleandomycin Action PathwayDrug actionSMP00730
Roxithromycin Action PathwayDrug actionSMP00251
Amikacin Action PathwayDrug actionSMP00253
Spectinomycin Action PathwayDrug actionSMP00258
Lymecycline Action PathwayDrug actionSMP00295
Lincomycin Action PathwayDrug actionSMP00728
Erythromycin Action PathwayDrug actionSMP00250
Telithromycin Action PathwayDrug actionSMP00252
Netilmicin Action PathwayDrug actionSMP00257
Tetracycline Action PathwayDrug actionSMP00294
Tigecycline Action PathwayDrug actionSMP00712
Paromomycin Action PathwayDrug actionSMP00714
Methacycline Action PathwayDrug actionSMP00727
Clindamycin Action PathwayDrug actionSMP00249
Neomycin Action PathwayDrug actionSMP00256
Doxycycline Action PathwayDrug actionSMP00291
Oxytetracycline Action PathwayDrug actionSMP00293
Tobramycin Action PathwayDrug actionSMP00711
Arbekacin Action PathwayDrug actionSMP00713
Rolitetracycline Action PathwayDrug actionSMP00726
Josamycin Action PathwayDrug actionSMP00731
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.939
Blood Brain Barrier - 0.6054
Caco-2 permeable - 0.9009
P-glycoprotein substrate Non-substrate 0.7827
P-glycoprotein inhibitor I Non-inhibitor 0.9851
P-glycoprotein inhibitor II Non-inhibitor 0.9902
Renal organic cation transporter Non-inhibitor 0.9634
CYP450 2C9 substrate Non-substrate 0.8233
CYP450 2D6 substrate Non-substrate 0.8832
CYP450 3A4 substrate Non-substrate 0.8021
CYP450 1A2 substrate Non-inhibitor 0.8694
CYP450 2C9 substrate Non-inhibitor 0.9362
CYP450 2D6 substrate Non-inhibitor 0.9529
CYP450 2C19 substrate Non-inhibitor 0.9119
CYP450 3A4 substrate Non-inhibitor 0.8683
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9806
Ames test Non AMES toxic 0.9538
Carcinogenicity Non-carcinogens 0.6811
Biodegradation Ready biodegradable 0.844
Rat acute toxicity 1.2108 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9902
hERG inhibition (predictor II) Non-inhibitor 0.9826
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
L-threonine crystal4.57USDg
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 Solubility477.0ALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD00041
KEGG CompoundC00188
ChEBI16857
ChEMBLCHEMBL291747
PharmGKBPA451673
HETTHR
WikipediaL-Threonine
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(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

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 13:37