temocapril   Click here for help

GtoPdb Ligand ID: 11736

Synonyms: CS-622 | CS622
Approved drug
temocapril is an approved drug (Japan & Korea)
Compound class: Synthetic organic
Comment: Temocapril (CS-622) is an angiotensin converting enzyme (ACE) inhibitor prodrug [1].

temocapril is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 149.48
Molecular weight 476.14
XLogP 2.71
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCOC(=O)[C@@H](N[C@H]1CS[C@@H](CN(C1=O)CC(=O)O)c1cccs1)CCc1ccccc1
Isomeric SMILES CCOC(=O)[C@H](CCc1ccccc1)N[C@H]1CS[C@@H](CN(C1=O)CC(=O)O)c1cccs1
InChI InChI=1S/C23H28N2O5S2/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27)/t17-,18-,20-/m0/s1
InChI Key FIQOFIRCTOWDOW-BJLQDIEVSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. Japan (0)  |  Korea (0)
Is prodrug? Yes
Active form temocaprilat
IUPAC Name Click here for help
2-[(2S,6R)-6-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-5-oxo-2-thiophen-2-yl-1,4-thiazepan-4-yl]acetic acid
International Nonproprietary Names Click here for help
INN number INN
6712 temocapril
Synonyms Click here for help
CS-622 | CS622
Database Links Click here for help
CAS Registry No. 111902-57-9 (source: WHO INN list)
ChEMBL Ligand CHEMBL2110627
DrugBank Ligand DB08836
GtoPdb PubChem SID 458923771
PubChem CID 443874
Search Google for chemical match using the InChIKey FIQOFIRCTOWDOW-BJLQDIEVSA-N
Search Google for chemicals with the same backbone FIQOFIRCTOWDOW
Search PubMed clinical trials temocapril
Search PubMed titles temocapril
Search PubMed titles/abstracts temocapril
UniChem Compound Search for chemical match using the InChIKey FIQOFIRCTOWDOW-BJLQDIEVSA-N
UniChem Connectivity Search for chemical match using the InChIKey FIQOFIRCTOWDOW-BJLQDIEVSA-N

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MedChemExpress
Temocapril (links to external site)
Cat. No. HY-100713