lisinopril-tryptophan   Click here for help

GtoPdb Ligand ID: 7893

PDB Ligand
Compound class: Synthetic organic
Comment: Lisinopril-tryptophan (LisW-S), an analogue of the ACE inhibitor lisinopril, is highly selective for the C-domain corresponding to 631-1232. Note there is a crystal structure for the ligand in 2X95 but in the Drosophila, not the human enzyme.
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 8
Hydrogen bond donors 6
Rotatable bonds 16
Topological polar surface area 157.54
Molecular weight 494.25
XLogP 0.4
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES NCCCCC(C(=O)NC(C(=O)O)Cc1c[nH]c2c1cccc2)NC(C(=O)O)CCc1ccccc1
Isomeric SMILES NCCCC[C@@H](C(=O)N[C@@H](C(=O)O)Cc1c[nH]c2c1cccc2)N[C@H](C(=O)O)CCc1ccccc1
InChI InChI=1S/C27H34N4O5/c28-15-7-6-12-22(30-23(26(33)34)14-13-18-8-2-1-3-9-18)25(32)31-24(27(35)36)16-19-17-29-21-11-5-4-10-20(19)21/h1-5,8-11,17,22-24,29-30H,6-7,12-16,28H2,(H,31,32)(H,33,34)(H,35,36)/t22-,23-,24+/m0/s1
InChI Key JXNGDSIPMBNTNL-KMDXXIMOSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2S)-2-[[(2S)-6-amino-1-[[(1R)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-1-oxohexan-2-yl]amino]-4-phenylbutanoic acid
Database Links Click here for help
GtoPdb PubChem SID 223366216
PubChem CID 45480144
RCSB PDB Ligand X95
Search Google for chemical match using the InChIKey JXNGDSIPMBNTNL-KMDXXIMOSA-N
Search Google for chemicals with the same backbone JXNGDSIPMBNTNL
Search UniChem for chemical match using the InChIKey JXNGDSIPMBNTNL-KMDXXIMOSA-N
Search UniChem for chemicals with the same backbone JXNGDSIPMBNTNL