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CHEBI:8774 - ramipril

ChEBI IDCHEBI:8774
ChEBI Nameramipril
Stars
DefinitionA 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.
Last Modified1 August 2024
DownloadsMolfile
FormulaC23H32N2O5
Net Charge0
Average Mass416.518
Monoisotopic Mass416.23112
SMILES[H][C@@]12CCC[C@]1([H])N(C(=O)[C@H](C)N[C@@H](CCc1ccccc1)C(=O)OCC)[C@H](C(=O)O)C2
InChIInChI=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
InChIKeyHDACQVRGBOVJII-JBDAPHQKSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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).
Applications:
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).
ChEBI Ontology
Outgoing Relation(s)
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)
ramipril (CHEBI:8774) is conjugate acid of ramipril(1−) (CHEBI:231704)
Incoming Relation(s)
ramipril(1−) (CHEBI:231704) is conjugate base of ramipril (CHEBI:8774)
IUPAC Name 
(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-ethoxycarbonyl-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid
INN  Source
ramiprilChemIDplus
Synonyms  Source
(2S-(1(R*(R*)),2alpha,3abeta,6abeta))-1-(2-((1-(Ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acidChemIDplus
Altace (TN)KEGG DRUG
RamiprilKEGG DRUG
RamiprilumDrugBank
TritaceChemIDplus
Manual XrefsDatabases
1888VSDB
2356DrugCentral
D00421KEGG DRUG
DB00178DrugBank
HMDB0014324HMDB
LSM-5950LINCS
RamiprilWikipedia
Registry NumbersSources
Reaxys:4214464Reaxys
CAS:87333-19-5KEGG DRUG
CAS:87333-19-5ChemIDplus
Citations