CHEBI:8774 - ramipril

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ChEBI Name ramipril
ChEBI ID CHEBI:8774
Definition A dipeptide that is the prodrug for ramiprilat, the active metabolite obtained by hydrolysis of the ethyl ester group. An angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H32N2O5
Net Charge 0
Average Mass 416.51060
Monoisotopic Mass 416.231
InChI InChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1
InChIKey HDACQVRGBOVJII-JBDAPHQKSA-N
SMILES CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1[C@H]2CCC[C@H]2C[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): matrix metalloproteinase inhibitor

bradykinin receptor B2 agonist
A bradykinin agonist that binds to and activates bradykinin B2 receptors.
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): prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
cardioprotective agent
Any protective agent that is able to prevent damage to the heart.
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ramipril (CHEBI:8774) has role bradykinin receptor B2 agonist (CHEBI:77496)
ramipril (CHEBI:8774) has role cardioprotective agent (CHEBI:77307)
ramipril (CHEBI:8774) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
ramipril (CHEBI:8774) has role matrix metalloproteinase inhibitor (CHEBI:50664)
ramipril (CHEBI:8774) has role prodrug (CHEBI:50266)
ramipril (CHEBI:8774) is a azabicycloalkane (CHEBI:38295)
ramipril (CHEBI:8774) is a cyclopentapyrrole (CHEBI:38296)
ramipril (CHEBI:8774) is a dicarboxylic acid monoester (CHEBI:36244)
ramipril (CHEBI:8774) is a dipeptide (CHEBI:46761)
ramipril (CHEBI:8774) is a ethyl ester (CHEBI:23990)
IUPAC Name
(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-ethoxycarbonyl-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
INN Source
ramipril ChemIDplus
Synonyms Sources
(2S-(1(R*(R*)),2alpha,3abeta,6abeta))-1-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid ChemIDplus
Altace (TN) KEGG DRUG
Ramipril KEGG DRUG
Ramiprilum DrugBank
Tritace ChemIDplus
Database Links Databases
2356 DrugCentral
D00421 KEGG DRUG
DB00178 DrugBank
HMDB0014324 HMDB
LSM-5950 LINCS
Ramipril Wikipedia
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Registry Numbers Types Sources
4214464 Beilstein Registry Number Beilstein
4214464 Reaxys Registry Number Reaxys
87333-19-5 CAS Registry Number ChemIDplus
87333-19-5 CAS Registry Number KEGG DRUG
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Last Modified
22 February 2017