captopril (CHEBI:3380)

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ChEBI Name	captopril

ChEBI ID	CHEBI:3380

Definition	A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group. It is used as an anti-hypertensive ACE inhibitor drug.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C9H15NO3S

Net Charge

Average Mass

217.28500

Monoisotopic Mass

217.07726

InChI

InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1

InChIKey

FAKRSMQSSFJEIM-RQJHMYQMSA-N

SMILES

C[C@H](CS)C(=O)N1CCC[C@H]1C(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 3.4.15.1 (peptidyl-dipeptidase A) inhibitor An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).

Application(s):	EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). antihypertensive agent Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.

ChEBI Ontology
Outgoing	captopril (CHEBI:3380) has role antihypertensive agent (CHEBI:35674) captopril (CHEBI:3380) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457) captopril (CHEBI:3380) is a N-acylpyrrolidine (CHEBI:46766) captopril (CHEBI:3380) is a L-proline derivative (CHEBI:84186) captopril (CHEBI:3380) is a alkanethiol (CHEBI:47908) captopril (CHEBI:3380) is a pyrrolidinemonocarboxylic acid (CHEBI:46701)

Incoming	captopril disulfide (CHEBI:53236) has functional parent captopril (CHEBI:3380)

IUPAC Name

1-[(2S)-2-methyl-3-sulfanylpropanoyl]-L-proline

Synonyms	Sources
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid	ChEBI
Captopryl	DrugBank
CP	ChEBI
D-2-methyl-3-mercaptopropanoyl-L-proline	ChemIDplus
D-3-mercapto-2-methylpropanoyl-L-proline	ChemIDplus
L-Captopril	DrugBank

Last Modified

22 February 2017