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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1237
CHEMBL1237
Compound Name LISINOPRIL
ChEMBL Synonyms QBRELIS | LISINOPRIL | CARACE | ZESTRIL | Lisinopril hydrate | ACEMIN | LISOPRESS | MK-521 | PRINIVIL | Zestril
Max Phase 4 (Approved)
Trade Names PRINIVIL | QBRELIS | ACEMIN | Zestril | ZESTRIL | LISOPRESS | LISINOPRIL | CARACE
Molecular Formula C21H31N3O5

Additional synonyms for CHEMBL1237 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NCCCC[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N2CCC[C@H]2C(=O)O
Standard InChI InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)2 ...
Download InChI
Standard InChI Key RLAWWYSOJDYHDC-BZSNNMDCSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1237

Molecule Features

CHEMBL1237 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Angiotensin-converting enzyme inhibitor Angiotensin-converting enzyme FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Cardiovascular DiseasesD002318EFO:0000319cardiovascular disease4ATC
Myocardial InfarctionD009203EFO:0000612myocardial infarction4FDA
HypertensionD006973EFO:0000537hypertension4FDA
Heart FailureD006333EFO:0000373congestive heart failure4FDA

Clinical Data

ClinicalTrials.gov LISINOPRIL
The Cochrane Collaboration LISINOPRIL

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL1237. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1808 Angiotensin-converting enzyme Homo sapiens 1.000
CHEMBL4074 Angiotensin-converting enzyme Oryctolagus cuniculus 1.000
CHEMBL2625 Angiotensin-converting enzyme Rattus norvegicus 1.000
CHEMBL3369 Neprilysin Rattus norvegicus 1.000
CHEMBL3768 Neprilysin Oryctolagus cuniculus 1.000
CHEMBL3769 Trypsin I Bos taurus 1.000
CHEMBL2617 Tryptase beta-1 Homo sapiens 1.000
CHEMBL1801 Plasminogen Homo sapiens 1.000
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 1.000
CHEMBL204 Thrombin Homo sapiens 1.000
CHEMBL1944 Neprilysin Homo sapiens 1.000
CHEMBL3419 Carboxypeptidase B2 isoform A Homo sapiens 1.000
CHEMBL2461 Prolyl endopeptidase Sus scrofa 0.998
CHEMBL3976 Dipeptidyl peptidase II Homo sapiens 0.998
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.997
CHEMBL3736 Angiotensin-converting enzyme 2 Homo sapiens 0.996
CHEMBL332 Matrix metalloproteinase-1 Homo sapiens 0.994
CHEMBL284 Dipeptidyl peptidase IV Homo sapiens 0.992
CHEMBL268 Cathepsin K Homo sapiens 0.988
CHEMBL209 Trypsin I Homo sapiens 0.987



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1808 Angiotensin-converting enzyme Homo sapiens 1.000
CHEMBL4074 Angiotensin-converting enzyme Oryctolagus cuniculus 1.000
CHEMBL2625 Angiotensin-converting enzyme Rattus norvegicus 1.000
CHEMBL3369 Neprilysin Rattus norvegicus 1.000
CHEMBL3768 Neprilysin Oryctolagus cuniculus 1.000
CHEMBL3769 Trypsin I Bos taurus 1.000
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 1.000
CHEMBL2617 Tryptase beta-1 Homo sapiens 1.000
CHEMBL1944 Neprilysin Homo sapiens 1.000
CHEMBL2461 Prolyl endopeptidase Sus scrofa 1.000
CHEMBL204 Thrombin Homo sapiens 1.000
CHEMBL1801 Plasminogen Homo sapiens 1.000
CHEMBL1907 Aminopeptidase N Homo sapiens 1.000
CHEMBL3419 Carboxypeptidase B2 isoform A Homo sapiens 1.000
CHEMBL270 Mu opioid receptor Rattus norvegicus 1.000
CHEMBL4675 Tripeptidyl aminopeptidase Rattus norvegicus 1.000
CHEMBL284 Dipeptidyl peptidase IV Homo sapiens 1.000
CHEMBL332 Matrix metalloproteinase-1 Homo sapiens 0.999
CHEMBL209 Trypsin I Homo sapiens 0.998
CHEMBL3736 Angiotensin-converting enzyme 2 Homo sapiens 0.998

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
405.5 405.2264 1.24 12 132.96 ZWITTERION


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 4 0 8 5 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
2.18 10.5 3.47 .48 1 29 0.38

Structural Alerts

There are 3 structural alerts for CHEMBL1237. To view alerts please click here.

Compound Cross References

ATC C - CARDIOVASCULAR SYSTEM
C09 - AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
C09A - ACE INHIBITORS, PLAIN
C09AA - ACE inhibitors, plain
C09AA03 - lisinopril

ChemSpider ChemSpider:RLAWWYSOJDYHDC-BZSNNMDCSA-N
DailyMed lisinopril
PubChem SID: 50085996
Wikipedia Lisinopril

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1237



ACToR 76547-98-3 77726-95-5
Atlas lisinopril
BindingDB 50367879 66979
Brenda 101055
ChEBI 43755
ChemicalBook CB6117715
DrugBank DB00722
DrugCentral 1587
eMolecules 4775693
EPA CompTox Dashboard DTXSID6040537
FDA SRS 7Q3P4BS2FD
Guide to Pharmacology 6360
Human Metabolome Database HMDB0001938
IBM Patent System E032B07CE857CD02AFB5ED67CC5BF6A6
LINCS LSM-5756
Mcule MCULE-7813362088 MCULE-5869146518
MolPort MolPort-002-507-428
Nikkaji J32.520A
PDBe LPR
PharmGKB PA450242
PubChem 11865407 5362119
PubChem: Drugs of the Future 12013163
PubChem: Thomson Pharma 14830773 14806092
Selleck lisinopril-zestril
SureChEMBL SCHEMBL15680
ZINC ZINC000003812863

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/RLAWWYSOJDYHDC-BZSNNMDCSA-N spacer
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