Tryptophan

Identification

Summary

Tryptophan is an amino acid commonly found as a component of total parenteral nutrition.

Brand Names
Aminosyn II 7 %, Sulfite-free, Aminosyn-PF 7%, Clinimix 2.75/5, Clinimix E 2.75/5, Clinisol 15, Freamine 6.9, Freamine III 10, Hepatamine 8, Nephramine, Olimel, Periolimel, Plenamine, Premasol, Primene, Procalamine 3, Prosol, Travasol 10, Trophamine 10 %, Tryptan
Generic Name
Tryptophan
DrugBank Accession Number
DB00150
Background

An essential amino acid that is necessary for normal growth in infants and for nitrogen balance in adults. It is a precursor of indole alkaloids in plants. It is a precursor of serotonin (hence its use as an antidepressant and sleep aid). It can be a precursor to niacin, albeit inefficiently, in mammals.

Type
Small Molecule
Groups
Approved, Nutraceutical, Withdrawn
Structure
Weight
Average: 204.2252
Monoisotopic: 204.089877638
Chemical Formula
C11H12N2O2
Synonyms
  • (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
  • (S)-alpha-Amino-beta-(3-indolyl)-propionic acid
  • (S)-Tryptophan
  • (S)-α-amino-1H-indole-3-propanoic acid
  • L-(-)-Tryptophan
  • L-(−)-tryptophan
  • L-Tryptophan
  • L-β-3-indolylalanine
  • Triptofano
  • Trp
  • Tryptophan
  • Tryptophane
  • Tryptophanum
  • W
External IDs
  • NSC-13119

Pharmacology

Indication

Tryptophan may be useful in increasing serotonin production, promoting healthy sleep, managing depression by enhancing mental and emotional well-being, managing pain tolerance, and managing weight.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for therapyAcute renal failure (arf)Combination Product in combination with: Leucine (DB00149), Methionine (DB00134), Isoleucine (DB00167), Threonine (DB00156), Phenylalanine (DB00120), Valine (DB00161), Histidine (DB00117), Lysine (DB00123)•••••••••••••••••••••• ••••••••
Used in combination for therapyChronic renal failure (crf)Combination Product in combination with: Leucine (DB00149), Methionine (DB00134), Isoleucine (DB00167), Valine (DB00161), Phenylalanine (DB00120), Threonine (DB00156), Lysine (DB00123), Histidine (DB00117)•••••••••••••••••••••• ••••••••
Used as adjunct in combination for symptomatic treatment ofDepression•••••••••••••••••••• ••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tryptophan is critical for the production of the body's proteins, enzymes and muscle tissue. It is also essential for the production of niacin, the synthesis of the neurotransmitter serotonin and melatonin. Tryptophan supplements can be used as natural relaxants to help relieve insomnia. Tryptophan can also reduce anxiety and depression and has been shown to reduce the intensity of migraine headaches. Other promising indications include the relief of chronic pain, reduction of impulsivity or mania and the treatment of obsessive or compulsive disorders. Tryptophan also appears to help the immune system and can reduce the risk of cardiac spasms. Tryptophan deficiencies may lead to coronary artery spasms. Tryptophan is used as an essential nutrient in infant formulas and intravenous feeding. Tryptophan is marketed as a prescription drug (Tryptan) for those who do not seem to respond well to conventional antidepressants. It may also be used to treat those afflicted with seasonal affective disorder (a winter-onset depression). Tryptopan serves as the precursor for the synthesis of serotonin (5-hydroxytryptamine, 5-HT) and melatonin (N-acetyl-5-methoxytryptamine).

Mechanism of action

A number of important side reactions occur during the catabolism of tryptophan on the pathway to acetoacetate. The first enzyme of the catabolic pathway is an iron porphyrin oxygenase that opens the indole ring. The latter enzyme is highly inducible, its concentration rising almost 10-fold on a diet high in tryptophan. Kynurenine is the first key branch point intermediate in the pathway. Kynurenine undergoes deamniation in a standard transamination reaction yielding kynurenic acid. Kynurenic acid and metabolites have been shown to act as antiexcitotoxics and anticonvulsives. A second side branch reaction produces anthranilic acid plus alanine. Another equivalent of alanine is produced further along the main catabolic pathway, and it is the production of these alanine residues that allows tryptophan to be classified among the glucogenic and ketogenic amino acids. The second important branch point converts kynurenine into 2-amino-3-carboxymuconic semialdehyde, which has two fates. The main flow of carbon elements from this intermediate is to glutarate. An important side reaction in liver is a transamination and several rearrangements to produce limited amounts of nicotinic acid, which leads to production of a small amount of NAD+ and NADP+.

TargetActionsOrganism
UTryptophan--tRNA ligase, cytoplasmic
inhibitor
Humans
UTryptophan--tRNA ligase
inhibitor
Geobacillus stearothermophilus
UTryptophan--tRNA ligase, mitochondrial
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic.

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Oral rat LD50: > 16 gm/kg. Investigated as a tumorigen, mutagen, reproductive effector. Symptoms of overdose include agitation, confusion, diarrhea, fever, overactive reflexes, poor coordination, restlessness, shivering, sweating, talking or acting with excitement you cannot control, trembling or shaking, twitching, and vomiting.

Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Tryptophan is combined with 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Tryptophan is combined with Acenocoumarol.
AcetazolamideThe risk or severity of CNS depression can be increased when Tryptophan is combined with Acetazolamide.
AcetophenazineThe risk or severity of CNS depression can be increased when Tryptophan is combined with Acetophenazine.
AgomelatineThe risk or severity of CNS depression can be increased when Tryptophan is combined with Agomelatine.
Food Interactions
No interactions found.

Products

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International/Other Brands
Alti-Tryptophan
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TryptanTablet1 gOralBausch Health, Canada Inc.1986-12-31Not applicableCanada flag
TryptanTablet250 mgOralBausch Health, Canada Inc.1999-01-06Not applicableCanada flag
TryptanCapsule500 mgOralBausch Health, Canada Inc.1986-12-31Not applicableCanada flag
TryptanTablet500 mgOralBausch Health, Canada Inc.1994-12-31Not applicableCanada flag
TryptanTablet750 mgOralBausch Health, Canada Inc.1999-01-06Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-tryptophanCapsule500 mgOralApotex Corporation2003-12-09Not applicableCanada flag
Apo-tryptophanTablet250 mgOralApotex CorporationNot applicableNot applicableCanada flag
Apo-tryptophanTablet1 gOralApotex Corporation2003-12-09Not applicableCanada flag
Apo-tryptophanTablet750 mgOralApotex Corporation2017-02-06Not applicableCanada flag
Apo-tryptophanTablet500 mgOralApotex Corporation2003-12-09Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseTryptophan (45 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (290 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Isoleucine (150 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Phenylalanine (140 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (145 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixTryptophan (45 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (260 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + Isoleucine (120 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (145 mg / 100 mL) + Phenylalanine hydrochloride (155 mg / 100 mL) + Proline (105 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (115 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada flag
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixTryptophan (45 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (260 mg / 100 mL) + Dextrose, unspecified form (10 g / 100 mL) + Glycine (520 mg / 100 mL) + Histidine (110 mg / 100 mL) + Isoleucine (120 mg / 100 mL) + L-Leucine hydrochloride (155 mg / 100 mL) + Lysine hydrochloride (195 mg / 100 mL) + Methionine (195 mg / 100 mL) + Phenylalanine hydrochloride (155 mg / 100 mL) + Proline (105 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (115 mg / 100 mL)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada flag
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexTryptophan (45 mg / 100 mL) + Alanine (520 mg / 100 mL) + Arginine (290 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (130.5 mg / 100 mL) + Glycine (260 mg / 100 mL) + Histidine (120 mg / 100 mL) + Isoleucine (150 mg / 100 mL) + Leucine (182.5 mg / 100 mL) + Lysine hydrochloride (145 mg / 100 mL) + Magnesium chloride (25.5 mg / 100 mL) + Methionine (100 mg / 100 mL) + Phenylalanine (140 mg / 100 mL) + Proline (170 mg / 100 mL) + Serine (125 mg / 100 mL) + Sodium acetate (170 mg / 100 mL) + Sodium chloride (29.3 mg / 100 mL) + Threonine (105 mg / 100 mL) + Tyrosine (10 mg / 100 mL) + Valine (145 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
2.75% Travas. Amino Acid InJ.W.elecw.25%dexTryptophan (49.5 mg / 100 mL) + Alanine (570 mg / 100 mL) + Arginine (316 mg / 100 mL) + Dextrose, unspecified form (25 g / 100 mL) + Dipotassium phosphate (261 mg / 100 mL) + Glycine (283 mg / 100 mL) + Histidine (132 mg / 100 mL) + Isoleucine (165 mg / 100 mL) + Leucine (201 mg / 100 mL) + Lysine hydrochloride (159.5 mg / 100 mL) + Magnesium chloride (51 mg / 100 mL) + Methionine (110 mg / 100 mL) + Phenylalanine (154 mg / 100 mL) + Proline (187 mg / 100 mL) + Serine (137.5 mg / 100 mL) + Sodium acetate (215.5 mg / 100 mL) + Sodium chloride (112 mg / 100 mL) + Threonine (115.5 mg / 100 mL) + Tyrosine (11 mg / 100 mL) + Valine (159.5 mg / 100 mL)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ClinimixTryptophan (0.50 g/1L) + Alanine (5.70 g/1L) + Arginine (3.17 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (75.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Lysine (2.00 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Phenylalanine (1.54 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tyrosine (0.11 g/1L) + Valine (1.60 g/1L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
ClinimixTryptophan (0.50 g/1L) + Alanine (5.70 g/1L) + Arginine (3.17 g/1L) + Calcium chloride dihydrate (0.33 g/1L) + D-glucose monohydrate (100.00 g/1L) + Dipotassium phosphate (2.61 g/1L) + Glycine (2.84 g/1L) + Histidine (1.32 g/1L) + Isoleucine (1.65 g/1L) + Leucine (2.01 g/1L) + Lysine (2.00 g/1L) + Magnesium chloride hexahydrate (0.51 g/1L) + Methionine (1.10 g/1L) + Phenylalanine (1.54 g/1L) + Proline (1.87 g/1L) + Serine (1.38 g/1L) + Sodium acetate trihydrate (2.16 g/1L) + Sodium chloride (1.12 g/1L) + Threonine (1.16 g/1L) + Tyrosine (0.11 g/1L) + Valine (1.60 g/1L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
ClinimixTryptophan (1.53 g/2L) + Alanine (17.60 g/2L) + Arginine (9.78 g/2L) + Calcium chloride dihydrate (0.66 g/2L) + D-glucose monohydrate (300.00 g/2L) + Dipotassium phosphate (5.22 g/2L) + Glycine (8.76 g/2L) + Histidine (4.08 g/2L) + Isoleucine (5.10 g/2L) + Leucine (6.20 g/2L) + Lysine (4.93 g/2L) + Magnesium chloride hexahydrate (1.02 g/2L) + Methionine (3.40 g/2L) + Phenylalanine (4.76 g/2L) + Proline (5.78 g/2L) + Serine (4.25 g/2L) + Sodium acetate trihydrate (5.94 g/2L) + Sodium chloride (1.54 g/2L) + Threonine (3.57 g/2L) + Tyrosine (0.34 g/2L) + Valine (4.93 g/2L)SolutionIntravenousBaxter Healthcare Corporation2017-10-252019-11-30US flag
FREAMINE III %10 1000 ML(SETLI)Tryptophan (0.15 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Phenylalanine (0.56 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Valine (0.66 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2013-01-292024-01-23Turkey flag
FREAMINE III %10 1000 ML(SETSIZ)Tryptophan (0.15 %) + Alanine (0.71 %) + Arginine (0.95 %) + Cysteine (0.016 %) + Glycine (1.4 %) + Histidine (0.28 %) + Isoleucine (0.69 %) + Leucine (0.91 %) + Lysine (0.73 %) + Methionine (0.53 %) + Phenylalanine (0.56 %) + Proline (1.12 %) + Serine (0.59 %) + Threonine (0.4 %) + Valine (0.66 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.2013-01-292024-01-23Turkey flag

Categories

ATC Codes
N06AX02 — Tryptophan
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolyl carboxylic acids and derivatives
Direct Parent
Indolyl carboxylic acids and derivatives
Alternative Parents
L-alpha-amino acids / 3-alkylindoles / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
3-alkylindole / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
proteinogenic amino acid, L-alpha-amino acid, tryptophan, erythrose 4-phosphate/phosphoenolpyruvate family amino acid (CHEBI:16828) / Common amino acids (C00078)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
8DUH1N11BX
CAS number
73-22-3
InChI Key
QIVBCDIJIAJPQS-VIFPVBQESA-N
InChI
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
IUPAC Name
(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
SMILES
N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

References

Synthesis Reference

Sten Vilhelm Gatenbeck, Per Olof Hedman, "Fermentative process for the production of L-tryptophan and its derivatives." U.S. Patent US3963572, issued April, 1974.

US3963572
General References
Not Available
Human Metabolome Database
HMDB0000929
KEGG Drug
D00020
KEGG Compound
C00078
PubChem Compound
6305
PubChem Substance
46508329
ChemSpider
6066
BindingDB
21974
RxNav
10898
ChEBI
16828
ChEMBL
CHEMBL54976
ZINC
ZINC000000083315
Therapeutic Targets Database
DAP001316
PharmGKB
PA10323
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
TRP
Wikipedia
Tryptophan
MSDS
Download (71.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCritically Ill Patients / Starvation1
4CompletedTreatmentAlzheimer's Disease (AD)1
4CompletedTreatmentDiabetic Nephropathy1
4RecruitingBasic ScienceHealthy Volunteers (HV) / Obesity / Type 2 Diabetes Mellitus1
4RecruitingPreventionIntestinal Obstruction / Laparotomy / Mesenteric vascular insufficiency1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amend
  • B. Braun Melsungen AG
  • Mason Distributors
  • V Sab Medical Labs Inc.
Dosage Forms
FormRouteStrength
SolutionParenteral
TabletOral
SolutionIntravenous10.50 g/1000ml
InjectionIntravenous0.5 g/l
InjectionIntravenous0.25 g/1000ml
Solution, concentrateIntravenous
InjectionIntravenous0.52 g/l
Injection, solutionIntravenous
InjectionIntravenous11.000 g/1000ml
SolutionIntravenous18.5 g/L
InjectionIntravenous5.5 g/1000ml
Drug delivery systemOral0.105 g
Injection, emulsionIntravenous
SolutionExtracorporeal
EmulsionIntravenous0.468 g
InjectionIntravenous16 g/1000ml
EmulsionParenteral20.000 g
InjectionIntravenous1.6 g/l
InjectionIntravenous0.37 g/l
Injection, solution, concentrateIntravenous
Injection, emulsionParenteral
EmulsionIntravenous0.466 g
Injection, emulsion; injection, solutionIntravenous
EmulsionParenteral
EmulsionIntravenous
Injection, solution
Injection, emulsionIntravenous4.656 g/1000ml
Injection, emulsionIntravenous6.792 g/1000ml
SolutionIntraperitoneal
Injection, solutionIntraperitoneal
LiquidHemodialysis
SolutionIntraperitoneal0.184 g/l
EmulsionIntravenous176 g/l
EmulsionIntravenous4 g
SolutionExtracorporeal; Intrabiliary; Intracardiac
EmulsionIntravenous3 g
SolutionIntravenous
TabletOral105.000 mg
InjectionIntravenous4 g/l
InjectionIntravenous0.21 g/100ml
LiquidIntravenous
EmulsionIntravenous13.000 g
EmulsionParenteral42.00 g
Injection, emulsionIntravenous14 g/1000ml
TabletOral67.000 mg
InjectionIntravenous10.30 g/l
CapsuleOral500 mg
TabletOral1 g
InjectionIntravenous
TabletOral250 mg
TabletOral500 mg
TabletOral750 mg
Prices
Unit descriptionCostUnit
Tryptan 1 g Tablet1.6USD tablet
Tryptan 750 mg Tablet1.2USD tablet
Apo-Tryptophan 1 g Tablet0.9USD tablet
Ratio-Tryptophan 1 g Tablet0.9USD tablet
Tryptan 500 mg Capsule0.8USD capsule
Tryptan 500 mg Tablet0.8USD tablet
L-tryptophan crystals0.72USD g
Apo-Tryptophan 500 mg Capsule0.45USD capsule
Apo-Tryptophan 500 mg Tablet0.45USD tablet
Pms-Tryptophan 500 mg Capsule0.45USD capsule
Pms-Tryptophan 500 mg Tablet0.45USD tablet
Ratio-Tryptophan 500 mg Capsule0.45USD capsule
Ratio-Tryptophan 500 mg Tablet0.45USD tablet
Tryptan 250 mg Tablet0.4USD tablet
L-tryptophan 500 mg capsule0.33USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)290.5 dec °CPhysProp
water solubility1.34E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.06HANSCH,C ET AL. (1995)
logS-1.23ADME Research, USCD
pKa7.38 (at 25 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility1.36 mg/mLALOGPS
logP-1.1ALOGPS
logP-1.1Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.54Chemaxon
pKa (Strongest Basic)9.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area79.11 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity56.2 m3·mol-1Chemaxon
Polarizability21.05 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.984
Blood Brain Barrier+0.951
Caco-2 permeable-0.5943
P-glycoprotein substrateNon-substrate0.5988
P-glycoprotein inhibitor INon-inhibitor0.9951
P-glycoprotein inhibitor IINon-inhibitor0.9779
Renal organic cation transporterNon-inhibitor0.8805
CYP450 2C9 substrateNon-substrate0.8463
CYP450 2D6 substrateNon-substrate0.7897
CYP450 3A4 substrateNon-substrate0.7841
CYP450 1A2 substrateNon-inhibitor0.9531
CYP450 2C9 inhibitorNon-inhibitor0.9481
CYP450 2D6 inhibitorNon-inhibitor0.9307
CYP450 2C19 inhibitorNon-inhibitor0.9644
CYP450 3A4 inhibitorNon-inhibitor0.9432
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9542
Ames testNon AMES toxic0.9284
CarcinogenicityNon-carcinogens0.931
BiodegradationNot ready biodegradable0.8348
Rat acute toxicity1.1785 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9864
hERG inhibition (predictor II)Non-inhibitor0.9402
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.51 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0udi-0190000000-feaec8547634dddcad8c
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0udi-0390000000-45a6c4fd79081597d44a
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0udi-0290000000-34f7274f31a4cb321a0b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)GC-MSsplash10-0fk9-9270000000-9761607cbe821f87f172
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-001i-0900000000-3faeed7ad32e1755c03c
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0udi-0290000000-9c57a732e337fade3cb6
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0560-4900000000-fa932bc4cffed0ca66b7
GC-MS Spectrum - EI-BGC-MSsplash10-001i-0900000000-d054a214c1717940989f
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-0290000000-9860799c854e5c9ac1c7
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0190000000-feaec8547634dddcad8c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0390000000-45a6c4fd79081597d44a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0udi-0290000000-34f7274f31a4cb321a0b
GC-MS Spectrum - GC-EI-QQGC-MSsplash10-0udi-3729000000-86129db57aaf1a245f93
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0fk9-9270000000-9761607cbe821f87f172
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-0900000000-3faeed7ad32e1755c03c
GC-MS Spectrum - GC-MSGC-MSsplash10-0udi-0290000000-9c57a732e337fade3cb6
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0910000000-db5439a5499b19881720
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-014m-0900000000-cc4a579a29d19a1c0d44
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00kf-3900000000-a931a9df4c855603d06e
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-0290000000-5fa576241f151a3a01a2
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0900000000-417ea0b6e4e18e5fbde1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-38f5ce97d594f3e3f12d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-783ffff22f31096f238f
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0a4i-0290000000-3ced9d310dda312f8582
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-0002-0900000000-a050919a36b995d34553
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-1ddec73daead0ffadce4
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-a8c9c60f075a675f6629
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0290602010-c09c931538bff74ac400
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0900000000-0fed327c2a56f556e04c
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0090000000-98ec1c2c012e58eab924
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-00di-0090000000-fc77784da5d9b288d751
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0290601010-d6f94902c0cf639cb7bc
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0a4i-0900000000-27633a4f7ecfac45c730
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-0udi-0090000000-ee6cb8392b2e8d644bc1
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , NegativeLC-MS/MSsplash10-004i-0090000000-d81c86eceee1c9824b02
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0udi-0190000000-0e8b883dc8ab06c89d77
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0uxu-2940000000-cb35b9680612e19d8b3a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-014i-2900000000-7cc592351cc616b1d75f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-014i-1900000000-987615a0add5eb2c3169
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-014i-1900000000-f150d9d1e19c72d337a8
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0a4r-0690000000-ea2d79df0b56be85abdd
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000j-0900000000-585a12a5632c26e1132f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00kb-0900000000-6438d3945cf8a0273496
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014i-0900000000-4dd8bf52e2f41311bcac
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014l-3900000000-145917d0d3838036008d
MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , PositiveLC-MS/MSsplash10-0a4i-0090000000-ce0faa81be914aa3213a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0a4i-0290000000-d610ff81bf083fe2f959
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0a4r-0980000000-4d3890c0f8cc3ff974ee
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0uxr-2960000000-f4c878f3abb1609bb5c5
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0090000000-c73c9b49139319c80b18
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0gb9-0930000000-da94834297fcc5b3d3c5
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-94061fd1f6b08445cdf3
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-e78172f4f27df232466e
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-93406e2cdb79770abc7d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0udi-0190000000-0e8b883dc8ab06c89d77
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0uxu-2940000000-cb35b9680612e19d8b3a
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-2900000000-5187dac98dbd6834d6ba
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-1900000000-987615a0add5eb2c3169
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-1900000000-174bb4d4390c75ae9a09
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-0fed327c2a56f556e04c
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0090000000-98ec1c2c012e58eab924
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00di-0090000000-fc77784da5d9b288d751
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0900000000-27633a4f7ecfac45c730
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0udi-0090000000-ee6cb8392b2e8d644bc1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-004i-0090000000-d81c86eceee1c9824b02
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0uxr-2960000000-f4c878f3abb1609bb5c5
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4i-0900000000-03946c55ea12f371c0f4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0910000000-b2a15c37af9ae0c2c71b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000b-0900000000-a7ab882061d0ea0246bd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kg-0900000000-daa1ca87bd3e17326b4b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014l-0900000000-1427d47465a86f57a89c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014l-0900000000-3d0c62136805cda149ab
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-c85ba4facf645f32c4c7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-a765305b14a15909ae5b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kg-0900000000-b1fdf0c754d5a54a9297
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4r-0690000000-ea2d79df0b56be85abdd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000j-0900000000-585a12a5632c26e1132f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00kb-0900000000-6438d3945cf8a0273496
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0900000000-4dd8bf52e2f41311bcac
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014l-3900000000-6f82948a09684218ff98
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-8043bd8b5eec986610ca
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-8feb1564836a7c8cf7c3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-08ec725ead6beef6f58f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-cc72882cc54fd067136d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-5a28995ec71c65d15d95
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-417ea0b6e4e18e5fbde1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-38f5ce97d594f3e3f12d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-783ffff22f31096f238f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-a050919a36b995d34553
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-1ddec73daead0ffadce4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-a8c9c60f075a675f6629
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0290000000-d610ff81bf083fe2f959
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4r-0980000000-4d3890c0f8cc3ff974ee
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-8f9f550ed2290da4414b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03di-1190000000-1cdadf5d6ffa43da1f41
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0920000000-07e999cba4b151f3150a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0790000000-30cd6abfcebca2a214d6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9030000000-cec5694440c14a657ed4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-9300000000-e1bf6616428367245601
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-0920000000-08a299abe7f22921a7a7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lr-1900000000-0d137acc00c57e0d0325
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fr6-0900000000-2a47b6fc13297ce240d7
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-152.0502228
predicted
DarkChem Lite v0.1.0
[M-H]-151.1936497
predicted
DarkChem Standard v0.1.0
[M-H]-152.0445228
predicted
DarkChem Lite v0.1.0
[M-H]-151.9399228
predicted
DarkChem Lite v0.1.0
[M-H]-151.8792228
predicted
DarkChem Lite v0.1.0
[M-H]-140.75209
predicted
DeepCCS 1.0 (2019)
[M+H]+152.3454228
predicted
DarkChem Lite v0.1.0
[M+H]+149.5914746
predicted
DarkChem Standard v0.1.0
[M+H]+152.5432228
predicted
DarkChem Lite v0.1.0
[M+H]+152.4650228
predicted
DarkChem Lite v0.1.0
[M+H]+152.4852228
predicted
DarkChem Lite v0.1.0
[M+H]+143.14769
predicted
DeepCCS 1.0 (2019)
[M+Na]+151.9208228
predicted
DarkChem Lite v0.1.0
[M+Na]+155.7324312
predicted
DarkChem Standard v0.1.0
[M+Na]+151.9815228
predicted
DarkChem Lite v0.1.0
[M+Na]+152.0007228
predicted
DarkChem Lite v0.1.0
[M+Na]+151.8520228
predicted
DarkChem Lite v0.1.0
[M+Na]+149.28648
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Tryptophan-trna ligase activity
Specific Function
Isoform 1, isoform 2 and T1-TrpRS have aminoacylation activity while T2-TrpRS lacks it. Isoform 2, T1-TrpRS and T2-TrpRS possess angiostatic activity whereas isoform 1 lacks it. T2-TrpRS inhibits f...
Gene Name
WARS
Uniprot ID
P23381
Uniprot Name
Tryptophan--tRNA ligase, cytoplasmic
Molecular Weight
53164.91 Da
References
  1. Tsuchiya W, Umehara T, Kuno A, Hasegawa T: Determination of tryptophan tRNA recognition sites for tryptophanyl-tRNA synthetase from hyperthermophilic archaeon, Aeropyrum pernix K1. Nucleic Acids Symp Ser (Oxf). 2004;(48):185-6. [Article]
  2. Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [Article]
  3. Zhu L, Ji F, Wang Y, Zhang Y, Liu Q, Zhang JZ, Matsushima K, Cao Q, Zhang Y: Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. J Immunol. 2006 Dec 1;177(11):8226-33. [Article]
  4. Yadav MC, Burudi EM, Alirezaei M, Flynn CC, Watry DD, Lanigan CM, Fox HS: IFN-gamma-induced IDO and WRS expression in microglia is differentially regulated by IL-4. Glia. 2007 Oct;55(13):1385-96. [Article]
  5. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [Article]
Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Tryptophan-trna ligase activity
Specific Function
Not Available
Gene Name
trpS
Uniprot ID
P00953
Uniprot Name
Tryptophan--tRNA ligase
Molecular Weight
37192.385 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. [Article]
  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. [Article]
  3. Tsuchiya W, Umehara T, Kuno A, Hasegawa T: Determination of tryptophan tRNA recognition sites for tryptophanyl-tRNA synthetase from hyperthermophilic archaeon, Aeropyrum pernix K1. Nucleic Acids Symp Ser (Oxf). 2004;(48):185-6. [Article]
  4. Kovaleva GK, Favorova OO, Moroz SG, Krauspe R, Kiselev LL: [Active intermediate compound of tryptophanyl-tRNA-synthetase with tryptophan]. Dokl Akad Nauk SSSR. 1976;229(2):492-5. [Article]
  5. Kovaleva GK, Degtiarev SKh, Favorova OO: [Affinity modification of tryptophanyl-tRNA synthetase by an alkylating L-tryptophan analog]. Mol Biol (Mosk). 1979 Nov-Dec;13(6):1237-46. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Tryptophan-trna ligase activity
Specific Function
Not Available
Gene Name
WARS2
Uniprot ID
Q9UGM6
Uniprot Name
Tryptophan--tRNA ligase, mitochondrial
Molecular Weight
40146.265 Da
References
  1. Paley EL, Denisova G, Sokolova O, Posternak N, Wang X, Brownell AL: Tryptamine induces tryptophanyl-tRNA synthetase-mediated neurodegeneration with neurofibrillary tangles in human cell and mouse models. Neuromolecular Med. 2007;9(1):55-82. [Article]
  2. Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [Article]
  3. Banin E, Dorrell MI, Aguilar E, Ritter MR, Aderman CM, Smith AC, Friedlander J, Friedlander M: T2-TrpRS inhibits preretinal neovascularization and enhances physiological vascular regrowth in OIR as assessed by a new method of quantification. Invest Ophthalmol Vis Sci. 2006 May;47(5):2125-34. [Article]
  4. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [Article]
  5. Charriere F, Helgadottir S, Horn EK, Soll D, Schneider A: Dual targeting of a single tRNA(Trp) requires two different tryptophanyl-tRNA synthetases in Trypanosoma brucei. Proc Natl Acad Sci U S A. 2006 May 2;103(18):6847-52. Epub 2006 Apr 24. [Article]

Enzymes

Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Tryptophan-trna ligase activity
Specific Function
Not Available
Gene Name
trpS
Uniprot ID
P00953
Uniprot Name
Tryptophan--tRNA ligase
Molecular Weight
37192.385 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. [Article]
  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. [Article]
  3. Tsuchiya W, Umehara T, Kuno A, Hasegawa T: Determination of tryptophan tRNA recognition sites for tryptophanyl-tRNA synthetase from hyperthermophilic archaeon, Aeropyrum pernix K1. Nucleic Acids Symp Ser (Oxf). 2004;(48):185-6. [Article]
  4. Kovaleva GK, Favorova OO, Moroz SG, Krauspe R, Kiselev LL: [Active intermediate compound of tryptophanyl-tRNA-synthetase with tryptophan]. Dokl Akad Nauk SSSR. 1976;229(2):492-5. [Article]
  5. Kovaleva GK, Degtiarev SKh, Favorova OO: [Affinity modification of tryptophanyl-tRNA synthetase by an alkylating L-tryptophan analog]. Mol Biol (Mosk). 1979 Nov-Dec;13(6):1237-46. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Tryptophan-trna ligase activity
Specific Function
Not Available
Gene Name
WARS2
Uniprot ID
Q9UGM6
Uniprot Name
Tryptophan--tRNA ligase, mitochondrial
Molecular Weight
40146.265 Da
References
  1. Paley EL, Denisova G, Sokolova O, Posternak N, Wang X, Brownell AL: Tryptamine induces tryptophanyl-tRNA synthetase-mediated neurodegeneration with neurofibrillary tangles in human cell and mouse models. Neuromolecular Med. 2007;9(1):55-82. [Article]
  2. Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [Article]
  3. Banin E, Dorrell MI, Aguilar E, Ritter MR, Aderman CM, Smith AC, Friedlander J, Friedlander M: T2-TrpRS inhibits preretinal neovascularization and enhances physiological vascular regrowth in OIR as assessed by a new method of quantification. Invest Ophthalmol Vis Sci. 2006 May;47(5):2125-34. [Article]
  4. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [Article]
  5. Charriere F, Helgadottir S, Horn EK, Soll D, Schneider A: Dual targeting of a single tRNA(Trp) requires two different tryptophanyl-tRNA synthetases in Trypanosoma brucei. Proc Natl Acad Sci U S A. 2006 May 2;103(18):6847-52. Epub 2006 Apr 24. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Tryptophan 5-monooxygenase activity
Specific Function
Not Available
Gene Name
TPH1
Uniprot ID
P17752
Uniprot Name
Tryptophan 5-hydroxylase 1
Molecular Weight
50984.725 Da
References
  1. Pavon JA, Fitzpatrick PF: Insights into the catalytic mechanisms of phenylalanine and tryptophan hydroxylase from kinetic isotope effects on aromatic hydroxylation. Biochemistry. 2006 Sep 12;45(36):11030-7. [Article]
  2. Langfort J, Baranczuk E, Pawlak D, Chalimoniuk M, Lukacova N, Marsala J, Gorski J: The effect of endurance training on regional serotonin metabolism in the brain during early stage of detraining period in the female rat. Cell Mol Neurobiol. 2006 Oct-Nov;26(7-8):1327-42. Epub 2006 Aug 1. [Article]
  3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. [Article]
  4. Invernizzi RW: Role of TPH-2 in brain function: news from behavioral and pharmacologic studies. J Neurosci Res. 2007 Nov 1;85(14):3030-5. [Article]
  5. Neckameyer WS, Coleman CM, Eadie S, Goodwin SF: Compartmentalization of neuronal and peripheral serotonin synthesis in Drosophila melanogaster. Genes Brain Behav. 2007 Nov;6(8):756-69. Epub 2007 Mar 21. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Tryptophan 5-monooxygenase activity
Specific Function
Not Available
Gene Name
TPH2
Uniprot ID
Q8IWU9
Uniprot Name
Tryptophan 5-hydroxylase 2
Molecular Weight
56056.295 Da
References
  1. Lopez VA, Detera-Wadleigh S, Cardona I, Kassem L, McMahon FJ: Nested association between genetic variation in tryptophan hydroxylase II, bipolar affective disorder, and suicide attempts. Biol Psychiatry. 2007 Jan 15;61(2):181-6. Epub 2006 Jun 27. [Article]
  2. Kraus MR, Al-Taie O, Schafer A, Pfersdorff M, Lesch KP, Scheurlen M: Serotonin-1A receptor gene HTR1A variation predicts interferon-induced depression in chronic hepatitis C. Gastroenterology. 2007 Apr;132(4):1279-86. Epub 2007 Feb 25. [Article]
  3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. [Article]
  4. Invernizzi RW: Role of TPH-2 in brain function: news from behavioral and pharmacologic studies. J Neurosci Res. 2007 Nov 1;85(14):3030-5. [Article]
  5. Calcagno E, Canetta A, Guzzetti S, Cervo L, Invernizzi RW: Strain differences in basal and post-citalopram extracellular 5-HT in the mouse medial prefrontal cortex and dorsal hippocampus: relation with tryptophan hydroxylase-2 activity. J Neurochem. 2007 Nov;103(3):1111-20. Epub 2007 Jul 31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Tryptophan-trna ligase activity
Specific Function
Isoform 1, isoform 2 and T1-TrpRS have aminoacylation activity while T2-TrpRS lacks it. Isoform 2, T1-TrpRS and T2-TrpRS possess angiostatic activity whereas isoform 1 lacks it. T2-TrpRS inhibits f...
Gene Name
WARS
Uniprot ID
P23381
Uniprot Name
Tryptophan--tRNA ligase, cytoplasmic
Molecular Weight
53164.91 Da
References
  1. Tsuchiya W, Umehara T, Kuno A, Hasegawa T: Determination of tryptophan tRNA recognition sites for tryptophanyl-tRNA synthetase from hyperthermophilic archaeon, Aeropyrum pernix K1. Nucleic Acids Symp Ser (Oxf). 2004;(48):185-6. [Article]
  2. Retailleau P, Weinreb V, Hu M, Carter CW Jr: Crystal structure of tryptophanyl-tRNA synthetase complexed with adenosine-5' tetraphosphate: evidence for distributed use of catalytic binding energy in amino acid activation by class I aminoacyl-tRNA synthetases. J Mol Biol. 2007 May 25;369(1):108-28. Epub 2007 Mar 12. [Article]
  3. Zhu L, Ji F, Wang Y, Zhang Y, Liu Q, Zhang JZ, Matsushima K, Cao Q, Zhang Y: Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. J Immunol. 2006 Dec 1;177(11):8226-33. [Article]
  4. Yadav MC, Burudi EM, Alirezaei M, Flynn CC, Watry DD, Lanigan CM, Fox HS: IFN-gamma-induced IDO and WRS expression in microglia is differentially regulated by IL-4. Glia. 2007 Oct;55(13):1385-96. [Article]
  5. Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Tryptophan 2,3-dioxygenase activity
Specific Function
Catalyzes the first and rate limiting step of the catabolism of the essential amino acid tryptophan along the kynurenine pathway (PubMed:17671174). Involved in the peripheral immune tolerance, cont...
Gene Name
IDO1
Uniprot ID
P14902
Uniprot Name
Indoleamine 2,3-dioxygenase 1
Molecular Weight
45325.89 Da
References
  1. Agaugue S, Perrin-Cocon L, Coutant F, Andre P, Lotteau V: 1-Methyl-tryptophan can interfere with TLR signaling in dendritic cells independently of IDO activity. J Immunol. 2006 Aug 15;177(4):2061-71. [Article]
  2. Fallarino F, Gizzi S, Mosci P, Grohmann U, Puccetti P: Tryptophan catabolism in IDO+ plasmacytoid dendritic cells. Curr Drug Metab. 2007 Apr;8(3):209-16. [Article]
  3. Cozzi A, Zignego AL, Carpendo R, Biagiotti T, Aldinucci A, Monti M, Giannini C, Rosselli M, Laffi G, Moroni F: Low serum tryptophan levels, reduced macrophage IDO activity and high frequency of psychopathology in HCV patients. J Viral Hepat. 2006 Jun;13(6):402-8. [Article]
  4. Grohmann U, Volpi C, Fallarino F, Bozza S, Bianchi R, Vacca C, Orabona C, Belladonna ML, Ayroldi E, Nocentini G, Boon L, Bistoni F, Fioretti MC, Romani L, Riccardi C, Puccetti P: Reverse signaling through GITR ligand enables dexamethasone to activate IDO in allergy. Nat Med. 2007 May;13(5):579-86. Epub 2007 Apr 8. [Article]
  5. Zheng X, Koropatnick J, Li M, Zhang X, Ling F, Ren X, Hao X, Sun H, Vladau C, Franek JA, Feng B, Urquhart BL, Zhong R, Freeman DJ, Garcia B, Min WP: Reinstalling antitumor immunity by inhibiting tumor-derived immunosuppressive molecule IDO through RNA interference. J Immunol. 2006 Oct 15;177(8):5639-46. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. Rafice SA, Chauhan N, Efimov I, Basran J, Raven EL: Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Biochem Soc Trans. 2009 Apr;37(Pt 2):408-12. doi: 10.1042/BST0370408. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Tryptophan 2,3-dioxygenase activity
Specific Function
Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
Gene Name
TDO2
Uniprot ID
P48775
Uniprot Name
Tryptophan 2,3-dioxygenase
Molecular Weight
47871.215 Da
References
  1. Rafice SA, Chauhan N, Efimov I, Basran J, Raven EL: Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Biochem Soc Trans. 2009 Apr;37(Pt 2):408-12. doi: 10.1042/BST0370408. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name
DDC
Uniprot ID
P20711
Uniprot Name
Aromatic-L-amino-acid decarboxylase
Molecular Weight
53925.815 Da
References
  1. Tyce GM: Origin and metabolism of serotonin. J Cardiovasc Pharmacol. 1990;16 Suppl 3:S1-7. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Very active and specific thyroid hormone transporter. Stimulates cellular uptake of thyroxine (T4), triiodothyronine (T3), reverse triiodothyronine (rT3) and diidothyronine. Does not transport Leu,...
Gene Name
SLC16A2
Uniprot ID
P36021
Uniprot Name
Monocarboxylate transporter 8
Molecular Weight
59510.86 Da
References
  1. Friesema EC, Ganguly S, Abdalla A, Manning Fox JE, Halestrap AP, Visser TJ: Identification of monocarboxylate transporter 8 as a specific thyroid hormone transporter. J Biol Chem. 2003 Oct 10;278(41):40128-35. Epub 2003 Jul 18. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [Article]
  2. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48