CHEBI:3354 - candoxatrilat

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ChEBI Name candoxatrilat
ChEBI ID CHEBI:3354
Definition A dicarboxylic acid monoamide obtained by formal condensation between the amino group of cis-4-aminocyclohexanecarboxylic acid and the cyclopentanecarboxylic acid group of 1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentanecarboxylic acid. A potent inhibitor of neutral endopeptidase (NEP, neprilysin, EC 3.4.24.11), it is used as its 2,3-dihydro-1H-inden-5-yl ester prodrug in the treatment of chronic heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:380571
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Formula C20H33NO7
Net Charge 0
Average Mass 399.47850
Monoisotopic Mass 399.22570
InChI InChI=1S/C20H33NO7/c1-27-10-11-28-13-15(18(24)25)12-20(8-2-3-9-20)19(26)21-16-6-4-14(5-7-16)17(22)23/h14-16H,2-13H2,1H3,(H,21,26)(H,22,23)(H,24,25)/t14-,15-,16+/m0/s1
InChIKey ACZWIDANLCXHBM-HRCADAONSA-N
SMILES COCCOC[C@H](CC1(CCCC1)C(=O)N[C@H]1CC[C@H](CC1)C(O)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): EC 3.4.24.* (metalloendopeptidase) inhibitor
Any EC 3.4.* (hydrolases acting on peptide bond) inhibitor that interferes with the activity of a metalloendopeptidase (EC 3.4.24.*).
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ChEBI Ontology
Outgoing candoxatrilat (CHEBI:3354) has role EC 3.4.24.* (metalloendopeptidase) inhibitor (CHEBI:59107)
candoxatrilat (CHEBI:3354) is a dicarboxylic acid (CHEBI:35692)
candoxatrilat (CHEBI:3354) is a dicarboxylic acid monoamide (CHEBI:35735)
Incoming candoxatril (CHEBI:3353) has functional parent candoxatrilat (CHEBI:3354)
IUPAC Name
cis-4-[({1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentyl}carbonyl)amino]cyclohexanecarboxylic acid
INN Source
candoxatrilat KEGG DRUG
Synonyms Sources
4-({1-[(S)-2-Carboxy-3-(2-methoxy-ethoxy)-propyl]-cyclopentanecarbonyl}-amino)-cyclohexanecarboxylic acid ChEMBL
Candoxatrilat KEGG COMPOUND
candoxatrilate ChEBI
Manual Xrefs Databases
C11721 KEGG COMPOUND
D03349 KEGG DRUG
DB00616 DrugBank
View more database links
Registry Numbers Types Sources
123122-54-3 CAS Registry Number ChemIDplus
123898-42-0 CAS Registry Number KEGG COMPOUND
8365079 Beilstein Registry Number Beilstein
Last Modified
04 August 2014