L-tryptophan   Click here for help

GtoPdb Ligand ID: 717

Abbreviated name: L-Trp
PDB Ligand
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 3
Topological polar surface area 79.11
Molecular weight 204.09
XLogP -1.27
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OC(=O)C(Cc1c[nH]c2c1cccc2)N
Isomeric SMILES OC(=O)[C@H](Cc1c[nH]c2c1cccc2)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
1. Conigrave AD, Mun HC, Delbridge L, Quinn SJ, Wilkinson M, Brown EM. (2004)
L-amino acids regulate parathyroid hormone secretion.
J Biol Chem, 279 (37): 38151-9. [PMID:15234970]
2. Conigrave AD, Quinn SJ, Brown EM. (2000)
L-amino acid sensing by the extracellular Ca2+-sensing receptor.
Proc Natl Acad Sci USA, 97 (9): 4814-9. [PMID:10781086]
3. Isberg V, Andersen KB, Bisig C, Dietz GP, Bräuner-Osborne H, Gloriam DE. (2014)
Computer-aided discovery of aromatic l-α-amino acids as agonists of the orphan G protein-coupled receptor GPR139.
J Chem Inf Model, 54 (6): 1553-7. [PMID:24826842]
4. Liu C, Bonaventure P, Lee G, Nepomuceno D, Kuei C, Wu J, Li Q, Joseph V, Sutton SW, Eckert W et al.. (2015)
GPR139, an Orphan Receptor Highly Enriched in the Habenula and Septum, Is Activated by the Essential Amino Acids L-Tryptophan and L-Phenylalanine.
Mol Pharmacol, 88 (5): 911-25. [PMID:26349500]
5. Metzner L, Kottra G, Neubert K, Daniel H, Brandsch M. (2005)
Serotonin, L-tryptophan, and tryptamine are effective inhibitors of the amino acid transport system PAT1.
FASEB J, 19 (11): 1468-73. [PMID:16126914]
6. Pillai SM, Meredith D. (2011)
SLC36A4 (hPAT4) is a high affinity amino acid transporter when expressed in Xenopus laevis oocytes.
J Biol Chem, 286 (4): 2455-60. [PMID:21097500]
7. Sloan JL, Mager S. (1999)
Cloning and functional expression of a human Na(+) and Cl(-)-dependent neutral and cationic amino acid transporter B(0+).
J Biol Chem, 274 (34): 23740-5. [PMID:10446133]