CHEBI:141521 - trandolaprilat

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ChEBI Name trandolaprilat
ChEBI ID CHEBI:141521
Definition A heterobicyclic compound that is trandolapril in which the ethyl ester group has been hydrolysed to the corresponding acid group. It is the active metabolite of the prodrug trandolapril.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Supplier Information
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Formula C22H30N2O5
Net Charge 0
Average Mass 402.491
Monoisotopic Mass 402.21547
InChI InChI=1S/C22H30N2O5/c1-14(23-17(21(26)27)12-11-15-7-3-2-4-8-15)20(25)24-18-10-6-5-9-16(18)13-19(24)22(28)29/h2-4,7-8,14,16-19,23H,5-6,9-13H2,1H3,(H,26,27)(H,28,29)/t14-,16+,17-,18-,19-/m0/s1
InChIKey AHYHTSYNOHNUSH-HXFGRODQSA-N
SMILES [H][C@@]12C[C@H](N(C(=O)[C@H](C)N[C@@H](CCC3=CC=CC=C3)C(O)=O)[C@@]1([H])CCCC2)C(O)=O
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in blood plasma (BTO:0000118). See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
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).
drug metabolite

Application(s): antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
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 trandolaprilat (CHEBI:141521) has role antihypertensive agent (CHEBI:35674)
trandolaprilat (CHEBI:141521) has role drug metabolite (CHEBI:49103)
trandolaprilat (CHEBI:141521) has role EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (CHEBI:35457)
trandolaprilat (CHEBI:141521) has role human xenobiotic metabolite (CHEBI:76967)
trandolaprilat (CHEBI:141521) is a dicarboxylic acid (CHEBI:35692)
trandolaprilat (CHEBI:141521) is a dipeptide (CHEBI:46761)
trandolaprilat (CHEBI:141521) is a organic heterobicyclic compound (CHEBI:27171)
trandolaprilat (CHEBI:141521) is a secondary amino compound (CHEBI:50995)
trandolaprilat (CHEBI:141521) is a tertiary carboxamide (CHEBI:140326)
Incoming trandolapril (CHEBI:9649) has functional parent trandolaprilat (CHEBI:141521)
IUPAC Name
(2S,3aR,7aS)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]octahydro-1H-indole-2-carboxylic acid
INNs Sources
trandolaprilat WHO MedNet
trandolaprilat WHO MedNet
trandolaprilate WHO MedNet
trandolaprilatum WHO MedNet
Synonyms Sources
(2S,3aR,7aS)-1-((S)-N-((S)-1-carboxy-3-phenylpropyl)alanyl)hexahydro-2-indolinecarboxylic acid ChemIDplus
1-(2-((1-carboxy-3-phenylpropyl)amino)-1-oxopropyl)octahydro-1H-indole-2-carboxylic acid HMDB
RU 44403 ChemIDplus
RU-44403 ChEBI
RU44403 ChEBI
trandolapril diacid DrugBank
Manual Xrefs Databases
4576532 ChemSpider
C21515 KEGG COMPOUND
CN101302185 Patent
CN101460459 Patent
DB14209 DrugBank
HMDB0060583 HMDB
X93 PDBeChem
View more database links
Registry Numbers Types Sources
87679-71-8 CAS Registry Number ChemIDplus
8875886 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11409646 PubMed citation Europe PMC
12736518 PubMed citation Europe PMC
17117442 PubMed citation Europe PMC
20488190 PubMed citation Europe PMC
2478763 PubMed citation Europe PMC
2551273 PubMed citation Europe PMC
25864194 PubMed citation Europe PMC
2847673 PubMed citation Europe PMC
3383998 PubMed citation Europe PMC
7527094 PubMed citation Europe PMC
7527103 PubMed citation Europe PMC
7531766 PubMed citation Europe PMC
8258671 PubMed citation Europe PMC
8396059 PubMed citation Europe PMC
Last Modified
05 July 2021