L-tryptophan   Click here for help

GtoPdb Ligand ID: 717

Abbreviated name: L-Trp
PDB Ligand
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
InChI Key QIVBCDIJIAJPQS-VIFPVBQESA-N
Natural/Endogenous Targets
Target
CaS receptor
GPR139
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
L-Tryptophan hydroxylase 2
L-Aromatic amino-acid decarboxylase
L-Tryptophan hydroxylase 1
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Monocarboxylate transporter 10
Proton-coupled Amino acid Transporter 4 6
ATB0,+ 7
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CaS receptor Ligand is endogenous in the given species Hs Allosteric modulator Positive 2.6 – 4.4 pKd - 1-2
pKd 2.6 – 4.4 [1-2]
GPR139 Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 3.1 pKi - 4
pKi 3.1 (Ki 7.38x10-4 M) [4]
Description: Inhibition equilibrium constant from a radioligand membrane binding assay.
GPR139 Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 3.7 pEC50 - 3
pEC50 3.7 (EC50 2.2x10-4 M) [3]
GPR139 Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 4.6 pIC50 - 4
pIC50 4.6 (IC50 2.6x10-5 M) [4]
Description: Measured using a GTPγS assay in transfected COS7 cells.
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Proton-coupled Amino acid Transporter 1 Hs Inhibitor Inhibition 2.3 pKi - 5
pKi 2.3 (Ki 4.6x10-3 M) [5]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference