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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
(2S,3R)-(-)-Threonine
(2S)-threonine
2-Amino-3-hydroxybutyric acid
L-(-)-Threonine
L-2-Amino-3-hydroxybutyric acid
L-alpha-amino-beta-hydroxybutyric acid
L-Threonin
L-α-amino-β-hydroxybutyric acid
Thr
Threonine
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixBaxter Corporation Clintec Nutrition Division
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexClintec Nutrition Company
2.75% Travas. Amino Acid InJ.W.elecw.25%dexClintec Nutrition Company
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.Clintec Nutrition Company
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 20% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrlytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Without Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25%trav. Amino Acid InJ.W.O.elect.5%dext.Clintec Nutrition Company
4.25%travasol Amino Acid InJ.W.elecw.5%dex.Clintec Nutrition Company
5% Travasol Amino Acid Injection With Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
5% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
5% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
Aminoderm PoudreDesbergers LtÉe, Division Of Technilab Inc.
AminosynHospira, Inc.
Aminosyn 10%Hospira Healthcare Corporation
Aminosyn 10% W ElectrolytesAbbott Laboratories, Limited
Aminosyn 3.5% MAbbott Laboratories, Limited
Aminosyn 5%Hospira Healthcare Corporation
Aminosyn 7%Hospira Healthcare Corporation
Aminosyn 8.5%Hospira Healthcare Corporation
Aminosyn 8.5% Injection With ElectrolytesHospira Healthcare Corporation
Aminosyn II 10%Hospira Healthcare Corporation
Aminosyn II 10% With ElectrolytesHospira Healthcare Corporation
Aminosyn II 15%Hospira Healthcare Corporation
Aminosyn II 5% InjAbbott Laboratories, Limited
Aminosyn II 7% InjectionHospira Healthcare Corporation
Aminosyn II 7% M In 10% Dextrose(dual Chamber)Hospira Healthcare Corporation
Aminosyn II 7% With 10% DextroseHospira Healthcare Corporation
Aminosyn II 7% With 50% DextroseHospira Healthcare Corporation
Aminosyn II 8.5% InjectionHospira Healthcare Corporation
Aminosyn II 8.5% M In 20% Dextrose (dual Chamber)Hospira Healthcare Corporation
Aminosyn II 8.5% With 50% DextroseHospira Healthcare Corporation
Aminosyn II In Dextrose InjectionHospira Healthcare Corporation
Aminosyn II With ElectrolytesHospira, Inc.
Aminosyn RF InjectionHospira Healthcare Corporation
Aminosyn Sulfite FreeHospira, Inc.
Aminosyn-PF 10%Hospira Healthcare Corporation
Aminosyn-PF 7%Hospira Healthcare Corporation
Cicatrin PowderGlaxosmithkline Inc
ClinimixBaxter Corporation
Clinimix 2.5% Travasol Aa Without Electrolytes In 10% Dextrose InjecBaxter Corporation Clintec Nutrition Division
Clinimix EBaxter Corporation
Freamine HbcB. Braun Medical Inc.
Freamine IIIB. Braun Medical Inc.
NovamineHospira, Inc.
Olimel 4.4%Baxter Corporation
Olimel 5.7%Baxter Corporation
Primene 10%-liq IVClintec Nutrition Company
Quick Mix 2.5% Travasol Aa With Electrolytes With 25% Dextrose InjecBaxter Corporation Clintec Nutrition Division
Renamin (amino Acids) InjectionBaxter Corporation
TravasolBaxter Corporation
Travasol Amino Acid Inj 5.5%Baxter Corporation
Travasol Amino Acid Inj 8.5%Baxter Corporation
Travasol EBaxter Corporation
Travasol Inj Without Electrolytes 5.5%Baxter Corporation
Vamin 18 Electrolyte-freeFresenius Kabi Ab
Vamin NFresenius Kabi Ab
SaltsNot Available
Categories
UNII2ZD004190S
CAS number72-19-5
WeightAverage: 119.1192
Monoisotopic: 119.058243159
Chemical FormulaC4H9NO3
InChI KeyInChIKey=AYFVYJQAPQTCCC-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)[[email protected]](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.
Related Articles
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
Tobramycin Action PathwayDrug actionSMP00711
Arbekacin Action PathwayDrug actionSMP00713
Methacycline Action PathwayDrug actionSMP00727
Amikacin Action PathwayDrug actionSMP00253
Spectinomycin Action PathwayDrug actionSMP00258
Threonine and 2-Oxobutanoate DegradationMetabolicSMP00452
Clindamycin Action PathwayDrug actionSMP00249
Gentamicin Action PathwayDrug actionSMP00254
Netilmicin Action PathwayDrug actionSMP00257
Doxycycline Action PathwayDrug actionSMP00291
Minocycline Action PathwayDrug actionSMP00292
Lymecycline Action PathwayDrug actionSMP00295
Tigecycline Action PathwayDrug actionSMP00712
Clarithromycin Action PathwayDrug actionSMP00248
Erythromycin Action PathwayDrug actionSMP00250
Roxithromycin Action PathwayDrug actionSMP00251
Kanamycin Action PathwayDrug actionSMP00255
Neomycin Action PathwayDrug actionSMP00256
Clomocycline Action PathwayDrug actionSMP00262
Paromomycin Action PathwayDrug actionSMP00714
Rolitetracycline Action PathwayDrug actionSMP00726
Chloramphenicol Action PathwayDrug actionSMP00729
Azithromycin Action PathwayDrug actionSMP00247
Telithromycin Action PathwayDrug actionSMP00252
Streptomycin Action PathwayDrug actionSMP00259
Demeclocycline Action PathwayDrug actionSMP00290
Oxytetracycline Action PathwayDrug actionSMP00293
Tetracycline Action PathwayDrug actionSMP00294
Lincomycin Action PathwayDrug actionSMP00728
Troleandomycin Action PathwayDrug actionSMP00730
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 inhibitorNon-inhibitor0.9362
CYP450 2D6 inhibitorNon-inhibitor0.9529
CYP450 2C19 inhibitorNon-inhibitor0.9119
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Liquidintravenous
Powdertopical
Solutionintravenous
Injection, solutionintravenous
Injection, solution, concentrateintravenous
Emulsionintravenous
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)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-2zc0000000-045341234639d940688bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-2ze0000000-08f448150a2533471625View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-5z50000000-98a39d63665a1a1855ddView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-4zq0000000-82e1bd8ff2e302e6b51bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-ze00000000-85dce837b0f965e73c8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z200000000-221510fd551c0b52c362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-z400000000-6ee11649899572cd4867View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z11000000-fde7ef1951fddff4b817View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-yz00000000-2d7e5609618437e59272View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-z200000000-4b43567f4a446aed0828View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-fz00000000-45382d9abd25be948e5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0z00000000-071b61d3ea723715c1c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-z000000000-c8320d0556dbe72049caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-yz00000000-9945ecd06408cb733177View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-wz00000000-c9804e2bfc51ec0e8593View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0pz9831000-f96dba3c74726ede32deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-z000000000-94eeca12e76e23c1695eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0ze0000000-efff9b10ae39f6ce6095View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-06z0000000-74ab3cba7b57b1b1b681View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-4z00000000-d9348197a5df9756d30cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-z400000000-9008bb1dfd2806e9f87dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-z000000000-47fd01696817c86aecc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-z000000000-ba9cd5b3e37ded5d3764View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-7z00000000-3fa8bd5efd825e5ac3faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-z900000000-063cffd047551fca9ee6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-z000000000-8b82bffd35f30875a7c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-z000000000-1748dd9a759c98e1c5eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-z000000000-e9069de219196460cc61View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ReferencesNot 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

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Threonine synthase activity
Specific Function:
Not Available
Gene Name:
THNSL1
Uniprot ID:
Q8IYQ7
Molecular Weight:
83069.54 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Threonine-trna ligase activity
Specific Function:
Not Available
Gene Name:
TARS
Uniprot ID:
P26639
Molecular Weight:
83434.5 Da
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:17139284 ]
  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:17016423 ]
  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:12875846 ]
  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:15507440 ]
  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:9493271 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Threonine-trna ligase activity
Specific Function:
Not Available
Gene Name:
TARS2
Uniprot ID:
Q9BW92
Molecular Weight:
81035.345 Da
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:17644600 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular Weight:
55492.07 Da
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:11278508 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 13:37