temocaprilat   Click here for help

GtoPdb Ligand ID: 11737

Synonyms: compound 24c [PMID: 3669006] | RNH 5139 | RNH-5139 | RNH5139 | RS-5139 | RS5139
Compound class: Synthetic organic
Comment: Temocaprilat is the active metabolite of temocapril (the approved drug) [1]. It is a competitive inhibitor of angiotensin-converting enzyme (ACE), and it has antihypertensive activity.
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 7
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 160.48
Molecular weight 448.11
XLogP 1.97
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OC(=O)CN1C[C@H](SC[C@@H](C1=O)N[C@H](C(=O)O)CCc1ccccc1)c1cccs1
Isomeric SMILES C1[C@H](SC[C@@H](C(=O)N1CC(=O)O)N[C@@H](CCc1ccccc1)C(=O)O)c1cccs1
InChI InChI=1S/C21H24N2O5S2/c24-19(25)12-23-11-18(17-7-4-10-29-17)30-13-16(20(23)26)22-15(21(27)28)9-8-14-5-2-1-3-6-14/h1-7,10,15-16,18,22H,8-9,11-13H2,(H,24,25)(H,27,28)/t15-,16-,18-/m0/s1
Classification Click here for help
Compound class Synthetic organic
Prodrug temocapril
IUPAC Name Click here for help
(2S)-2-[[(2S,6R)-4-(carboxymethyl)-5-oxo-2-thiophen-2-yl-1,4-thiazepan-6-yl]amino]-4-phenylbutanoic acid
International Nonproprietary Names Click here for help
INN number INN
7673 temocaprilat
Synonyms Click here for help
compound 24c [PMID: 3669006] | RNH 5139 | RNH-5139 | RNH5139 | RS-5139 | RS5139
Database Links Click here for help
BindingDB Ligand 50024710
CAS Registry No. 110221-53-9 (source: WHO INN record)
ChEMBL Ligand CHEMBL300841
GtoPdb PubChem SID 458923772
PubChem CID 443151
Search Google for chemical match using the InChIKey KZVWEOXAPZXAFB-BQFCYCMXSA-N
Search Google for chemicals with the same backbone KZVWEOXAPZXAFB
Search PubMed clinical trials temocaprilat
Search PubMed titles temocaprilat
Search PubMed titles/abstracts temocaprilat
UniChem Compound Search for chemical match using the InChIKey KZVWEOXAPZXAFB-BQFCYCMXSA-N
UniChem Connectivity Search for chemical match using the InChIKey KZVWEOXAPZXAFB-BQFCYCMXSA-N