Identification

Name
L-Tryptophan
Accession Number
DB00150  (NUTR00058, EXPT02064)
Type
Small Molecule
Groups
Approved, Nutraceutical, Withdrawn
Description

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.

Structure
Thumb
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-β-3-indolylalanine
  • Trp
  • Tryptophan
  • W
External IDs
NSC-13119
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-tryptophanTablet1 gOralDominion PharmacalNot applicableNot applicableCanada
PHL-tryptophanCapsule500 mgOralPharmel Inc2005-03-232016-10-25Canada
PHL-tryptophanTablet1 gOralPharmel Inc1998-02-172016-10-25Canada
PHL-tryptophanTablet500 mgOralPharmel Inc2005-03-232016-10-25Canada
PMS-tryptophanCapsule500 mgOralPharmascience Inc2003-02-14Not applicableCanada
PMS-tryptophanTablet1 gOralPharmascience Inc1997-01-30Not applicableCanada
PMS-tryptophanTablet500 mgOralPharmascience Inc1999-09-01Not applicableCanada
Teva-tryptophanTablet1 gOralTeva1998-08-07Not applicableCanada
Teva-tryptophanTablet500 mgOralTeva1999-09-28Not applicableCanada
Teva-tryptophanCapsule500 mgOralTeva2000-02-23Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tryptophanTablet500 mgOralApotex Corporation2003-12-09Not applicableCanada
Apo-tryptophanTablet750 mgOralApotex Corporation2017-02-06Not applicableCanada
Apo-tryptophanTablet1 gOralApotex Corporation2003-12-09Not applicableCanada
Apo-tryptophanTablet250 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-tryptophanCapsule500 mgOralApotex Corporation2003-12-09Not applicableCanada
International/Other Brands
Alti-Tryptophan
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Tryptophan (45 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (260 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Histidine (120 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Serine (125 mg) + L-Threonine (105 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixL-Tryptophan (45 mg) + Dipotassium phosphate (130.5 mg) + Glucose (10 g) + Glycine (520 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Histidine (110 mg) + L-Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + L-Lysine hydrochloride (145 mg) + L-Methionine (145 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312015-08-05Canada
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixL-Tryptophan (45 mg) + Glucose (10 g) + Glycine (520 mg) + L-Alanine (520 mg) + L-Arginine (260 mg) + L-Histidine (110 mg) + L-Isoleucine (120 mg) + L-Leucine hydrochloride (155 mg) + L-Lysine hydrochloride (195 mg) + L-Methionine (195 mg) + L-Phenylalanine hydrochloride (155 mg) + L-Proline (105 mg) + L-Threonine (105 mg) + L-Tyrosine (10 mg) + L-Valine (115 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexL-Tryptophan (45 mg) + Dipotassium phosphate (130.5 mg) + Glucose (25 g) + Glycine (260 mg) + L-Alanine (520 mg) + L-Arginine (290 mg) + L-Histidine (120 mg) + L-Isoleucine (150 mg) + L-Leucine (182.5 mg) + L-Lysine (145 mg) + L-Methionine (100 mg) + L-Phenylalanine (140 mg) + L-Proline (170 mg) + L-Serine (125 mg) + L-Threonine (105 mg) + L-Tyrosine (10 mg) + L-Valine (145 mg) + Magnesium chloride (25.5 mg) + Sodium Chloride (29.3 mg) + Sodium acetate (170 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travas. Amino Acid InJ.W.elecw.25%dexL-Tryptophan (49.5 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (283 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Histidine (132 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Serine (137.5 mg) + L-Threonine (115.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)LiquidIntravenousClintec Nutrition Company1996-07-301998-08-13Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixL-Tryptophan (49.5 mg) + Dipotassium phosphate (261 mg) + Glucose (25 g) + Glycine (570 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Histidine (120.5 mg) + L-Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215.5 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-02-022007-08-02Canada
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixL-Tryptophan (49.5 mg) + Dipotassium phosphate (215.5 mg) + Glucose (5 g) + Glycine (570 mg) + L-Alanine (570 mg) + L-Arginine (285 mg) + L-Histidine (120.5 mg) + L-Isoleucine (131.5 mg) + L-Leucine hydrochloride (170 mg) + L-Lysine hydrochloride (159 mg) + L-Methionine (159 mg) + L-Phenylalanine hydrochloride (170 mg) + L-Proline (115 mg) + L-Threonine (115 mg) + L-Tyrosine (11 mg) + L-Valine (126 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (256 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1993-12-312007-08-02Canada
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.L-Tryptophan (49.5 mg) + Dipotassium phosphate (261 mg) + Glucose (5 g) + Glycine (283 mg) + L-Alanine (570 mg) + L-Arginine (316 mg) + L-Histidine (132 mg) + L-Isoleucine (165 mg) + L-Leucine (201 mg) + L-Lysine (159.5 mg) + L-Methionine (110 mg) + L-Phenylalanine (154 mg) + L-Proline (187 mg) + L-Serine (137.5 mg) + L-Threonine (115.5 mg) + L-Tyrosine (11 mg) + L-Valine (159.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (112 mg) + Sodium acetate (215 mg)LiquidIntravenousClintec Nutrition Company1996-12-311999-08-10Canada
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixL-Tryptophan (76 mg) + Glucose (20 g) + Glycine (880 mg) + L-Alanine (880 mg) + L-Arginine (440 mg) + L-Histidine (186 mg) + L-Isoleucine (203 mg) + L-Leucine hydrochloride (263 mg) + L-Lysine hydrochloride (246 mg) + L-Methionine (246 mg) + L-Phenylalanine hydrochloride (263 mg) + L-Proline (178 mg) + L-Threonine (178 mg) + L-Tyrosine (17 mg) + L-Valine (195 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1995-12-312007-08-02Canada
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseL-Tryptophan (76.5 mg) + Dipotassium phosphate (261 mg) + Glucose (10 g) + Glycine (438 mg) + L-Alanine (880 mg) + L-Arginine (489 mg) + L-Histidine (204 mg) + L-Isoleucine (255 mg) + L-Leucine (310 mg) + L-Lysine hydrochloride (246.5 mg) + L-Methionine (170 mg) + L-Phenylalanine (238 mg) + L-Proline (289 mg) + L-Serine (212.5 mg) + L-Threonine (178.5 mg) + L-Tyrosine (17 mg) + L-Valine (246.5 mg) + Magnesium chloride (51 mg) + Sodium Chloride (77 mg) + Sodium acetate (297 mg)SolutionIntravenousBaxter Corporation Clintec Nutrition Division1996-12-312015-08-05Canada
Categories
UNII
8DUH1N11BX
CAS number
73-22-3
Weight
Average: 204.2252
Monoisotopic: 204.089877638
Chemical Formula
C11H12N2O2
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[[email protected]@H](CC1=CNC2=CC=CC=C12)C(O)=O

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.

Structured Indications
Not Available
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
Human
UTryptophan--tRNA ligase
inhibitor
Geobacillus stearothermophilus
UTryptophan--tRNA ligase, mitochondrial
inhibitor
Human
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
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.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Tryptophan MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.Experimental
AlaproclateL-Tryptophan may increase the serotonergic activities of Alaproclate.Experimental
BenmoxinThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Benmoxin.Withdrawn
BrofaromineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Brofaromine.Experimental
CaroxazoneThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Caroxazone.Withdrawn
CitalopramL-Tryptophan may increase the serotonergic activities of Citalopram.Approved
DapoxetineL-Tryptophan may increase the serotonergic activities of Dapoxetine.Investigational
DesvenlafaxineL-Tryptophan may increase the serotonergic activities of Desvenlafaxine.Approved
DuloxetineL-Tryptophan may increase the serotonergic activities of Duloxetine.Approved
EscitalopramL-Tryptophan may increase the serotonergic activities of Escitalopram.Approved, Investigational
EtoperidoneL-Tryptophan may increase the serotonergic activities of Etoperidone.Approved
FluoxetineL-Tryptophan may increase the serotonergic activities of Fluoxetine.Approved, Vet Approved
FluvoxamineL-Tryptophan may increase the serotonergic activities of Fluvoxamine.Approved, Investigational
FurazolidoneThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Furazolidone.Approved, Vet Approved
HarmalineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Harmaline.Experimental
HydracarbazineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Hydracarbazine.Experimental
IndalpineL-Tryptophan may increase the serotonergic activities of Indalpine.Investigational, Withdrawn
IproclozideThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Iproclozide.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Iproniazid.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Isocarboxazid.Approved
LevomilnacipranL-Tryptophan may increase the serotonergic activities of Levomilnacipran.Approved
MebanazineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Mebanazine.Withdrawn
Methylene blueThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Methylene blue.Investigational
MilnacipranL-Tryptophan may increase the serotonergic activities of Milnacipran.Approved
MinaprineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Minaprine.Approved
MirtazapineL-Tryptophan may increase the serotonergic activities of Mirtazapine.Approved
MoclobemideThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Moclobemide.Approved
NefazodoneL-Tryptophan may increase the serotonergic activities of Nefazodone.Approved, Withdrawn
NialamideThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Nialamide.Withdrawn
OctamoxinThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Octamoxin.Withdrawn
PargylineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Pargyline.Approved
ParoxetineL-Tryptophan may increase the serotonergic activities of Paroxetine.Approved, Investigational
PhenelzineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Phenelzine.Approved
PheniprazineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Pheniprazine.Withdrawn
PhenoxypropazineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Phenoxypropazine.Withdrawn
PirlindoleThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Pirlindole.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Pivhydrazine.Withdrawn
RasagilineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Rasagiline.Approved
SafrazineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Safrazine.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineL-Tryptophan may increase the serotonergic activities of Sertraline.Approved
ToloxatoneThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Toloxatone.Approved
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Trans-2-Phenylcyclopropylamine.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Tranylcypromine.Approved
VenlafaxineL-Tryptophan may increase the serotonergic activities of Venlafaxine.Approved
ZimelidineL-Tryptophan may increase the serotonergic activities of Zimelidine.Withdrawn
Food Interactions
Not Available

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
External Links
Human Metabolome Database
HMDB00929
KEGG Drug
D00020
KEGG Compound
C00078
PubChem Compound
6305
PubChem Substance
46508329
ChemSpider
6066
BindingDB
21974
ChEBI
16828
ChEMBL
CHEMBL54976
Therapeutic Targets Database
DAP001316
PharmGKB
PA10323
IUPHAR
717
Guide to Pharmacology
GtP Drug Page
HET
TRP
Wikipedia
Tryptophan
ATC Codes
N06AX02 — Tryptophan
AHFS Codes
  • 28:16.04 — Antidepressants
  • 28:16.04.92 — Miscellaneous Antidepressants
MSDS
Download (71.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingSupportive CareProtein Feeding in Post-traumatic Injury Patients1
2Active Not RecruitingTreatmentCarcinoid Tumors / Medulloblastomas / Neuroblastomas / Neuroendocrine Tumors1
2CompletedTreatmentCocaine-Related Disorders1
2, 3RecruitingTreatmentSchizophrenic Disorders1
3CompletedTreatmentCritical Illness1
3CompletedTreatmentInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants / Sepsis1
4CompletedTreatmentAlzheimer's Disease (AD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionIntravenous
Injection, solution, concentrateIntravenous
EmulsionIntravenous
SolutionIntravenous
LiquidIntravenous
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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Indolyl carboxylic acid derivative / Alpha-amino acid / Alpha-amino acid or derivatives / L-alpha-amino acid / 3-alkylindole / Indole / Aralkylamine / Benzenoid / Substituted pyrrole / Heteroaromatic compound
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)

Targets

Kind
Protein
Organism
Human
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. [PubMed:17150540]
  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. [PubMed:17428498]
  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. [PubMed:17114500]
  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. [PubMed:17661345]
  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. [PubMed:16724112]
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. [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. 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. [PubMed:17150540]
  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. [PubMed:971661]
  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. [PubMed:547176]
Kind
Protein
Organism
Human
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. [PubMed:17114825]
  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. [PubMed:17428498]
  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. [PubMed:16639024]
  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. [PubMed:16724112]
  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. [PubMed:16636268]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:19290871]
Kind
Protein
Organism
Human
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. [PubMed:1369709]
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. [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. 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. [PubMed:17150540]
  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. [PubMed:971661]
  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. [PubMed:547176]
Kind
Protein
Organism
Human
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. [PubMed:17114825]
  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. [PubMed:17428498]
  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. [PubMed:16639024]
  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. [PubMed:16724112]
  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. [PubMed:16636268]
Kind
Protein
Organism
Human
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. [PubMed:16953590]
  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. [PubMed:16897368]
  3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. [PubMed:17519505]
  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. [PubMed:17492791]
  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. [PubMed:17376153]
Kind
Protein
Organism
Human
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. [PubMed:16806105]
  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. [PubMed:17408646]
  3. Nakamura K, Hasegawa H: Developmental role of tryptophan hydroxylase in the nervous system. Mol Neurobiol. 2007 Feb;35(1):45-54. [PubMed:17519505]
  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. [PubMed:17492791]
  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. [PubMed:17666043]
Kind
Protein
Organism
Human
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. [PubMed:17150540]
  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. [PubMed:17428498]
  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. [PubMed:17114500]
  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. [PubMed:17661345]
  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. [PubMed:16724112]
Kind
Protein
Organism
Human
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. [PubMed:16887964]
  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. [PubMed:17430109]
  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. [PubMed:16842443]
  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. [PubMed:17417651]
  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. [PubMed:17015752]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  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. [PubMed:19290871]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:12871948]
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
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. [PubMed:11827462]
  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. [PubMed:11278508]

Drug created on June 13, 2005 07:24 / Updated on October 23, 2017 14:13