Drug Information

General Information
Drug ID
DR00086
Drug Name
L-tryptophan
Synonyms
(-)-Tryptophan; (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid; (L)-TRYPTOPHAN; (S)-(-)-2-Amino-3-(3-indolyl)propionic Acid; (S)-(-)-Tryptopha n; (S)-(-)-Tryptophan; (S)-2-Amino-3-(1H-indol-3-yl)propanoic acid; (S)-2-Amino-3-(3-indolyl)propionic acid; (S)-Tryptophan; (S)-a-Amino-1H-indole-3-propanoic acid; (S)-a-Amino-b-indolepropionic acid; (S)-a-Aminoindole-3-propionic acid; (S)-alpha-Amino-1H-indole-3-propanoic acid; (S)-alpha-Amino-beta-indolepropionic acid; (S)-alpha-Aminoindole-3-propionic acid; (S)-alpha-amino-beta-(3-indolyl)-propionic acid; 1-beta-3-Indolylalanine; 151A3008-4CFE-40C9-AC0B-467EF0CB50EA; 1H-Indole-3-alanine; 1H-Indole-3-alanine (VAN); 1beta-3-Indolylalanine; 2-Amino-3-(lH-indol-3-yl)-propanoic acid; 2-Amino-3-indolylpropanoic acid; 2-amino-3-indol-3-ylpropionic acid; 3-Indol-3-ylalanine; Alanine, 3-indol-3-yl; Alpha'-Amino-3-indolepropionic acid; Alpha-Amino-beta-(3-indolyl)-propionic acid; Alpha-amino-beta-(3-indolyl)-pr opionic acid; Alti-Tryptophan; Ardeytropin; EH 121; H-Trp-oh; Indole-3-alanine; Kalma; L-(-)-Tryptophan; L-(-)-Tryptophane; L-TRYPTOPHAN SIGMA GRADE; L-Trp; L-Tryptofan; L-Tryptophan (9CI); L-Tryptophan (JP15); L-Tryptophane; L-Ttp; L-a-Aminoindole-3-propionic acid; L-alpha-Aminoindole-3-propionic acid; L-alpha-amino-3-indolepropionic acid; L-b-3-Indolylalanine; L-beta-3-Indolylalanine; LTR; Lyphan; MT1; Optimax; Pacitron; Propionic acid, 2-amino-3-indol-3-yl; S(-)-1-alpha-Aminoindole-3-propionic acid; Sedanoct; T 0254; TRP NH3+ COOH; TRP-01; Triptofano; Triptofano [Spanish]; Trofan; Trp; Tryptacin; Tryptan; Tryptophan; Tryptophan (H-3); Tryptophan (USP/INN); Tryptophan (VAN); Tryptophan [USAN:INN]; Tryptophan, L-(8CI); Tryptophane; Tryptophane [French]; Tryptophanum; Tryptophanum [Latin]
Drug Type
Small molecular drug
Indication Depression [ICD11:6A8Z] Approved [1]
Therapeutic Class
Antidepressants
Structure
3D MOL 2D MOL
Formula
C11H12N2O2
Canonical SMILES
C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)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
InChIKey
QIVBCDIJIAJPQS-VIFPVBQESA-N
CAS Number
CAS 73-22-3
Pharmaceutical Properties Molecular Weight 204.22 Topological Polar Surface Area 79.1
Heavy Atom Count 15 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
XLogP
-1.1
PubChem CID
6305
PubChem SID
10322924 ,10534147 ,11109884 ,11111851 ,11335632 ,11360871 ,11461843 ,11528964 ,14710264 ,14710293 ,14916602 ,15195597 ,17405739 ,24276916 ,24277675 ,24278135 ,24714971 ,24770171 ,24844224 ,24889916 ,24900200 ,24900575 ,25622645 ,26703933 ,26711994 ,26712808 ,3134836 ,3378 ,605298 ,6435732 ,6436701 ,7847088 ,7888703 ,7890877 ,7980851 ,8026883 ,8144649 ,8149576 ,8153976 ,820596 ,821032 ,822330 ,822480 ,823942 ,826461 ,830210 ,834088 ,841615 ,854680 ,855044
ChEBI ID
ChEBI:16828
TTD Drug ID
D05EJG
DT(s) Transporting This Drug LAT2 Transporter Info L-type amino acid transporter 2 Substrate [2]
MCT10 Transporter Info Monocarboxylate transporter 10 Substrate [3]
OAT3 Transporter Info Organic anion transporter 3 Substrate [4]
P-GP Transporter Info P-glycoprotein 1 Substrate [5]
PAT4 Transporter Info Proton-coupled amino acid transporter 4 Substrate [6]
References
1 Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198.
2 The Transporter Classification Database (TCDB): recent advances. Nucleic Acids Res. 2016 Jan 4;44(D1):D372-9. (ID: 2.A.3.8.20)
3 Phosphatidylserine synthesis required for the maximal tryptophan transport activity in Saccharomyces cerevisiae. Biosci Biotechnol Biochem. 2000 Jan;64(1):167-72.
4 Murine renal organic anion transporters mOAT1 and mOAT3 facilitate the transport of neuroactive tryptophan metabolites. Am J Physiol Cell Physiol. 2005 Nov;289(5):C1075-84.
5 Pharmacogenetics of antidepressants. Front Pharmacol. 2011 Feb 16;2:6.
6 SLC36A4 (hPAT4) is a high affinity amino acid transporter when expressed in Xenopus laevis oocytes. J Biol Chem. 2011 Jan 28;286(4):2455-60.

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