Enalapril (CHEM016685)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:40:27 UTC
Update Date2026-04-13 20:33:40 UTC
Accession NumberCHEM016685
Identification
Common NameEnalapril
ClassSmall Molecule
DescriptionEnalapril is a prodrug belonging to the angiotensin-converting enzyme (ACE) inhibitor drug class that works on the renin-angiotensin-aldosterone system, which is responsible for the regulation of blood pressure and fluid and electrolyte homeostasis. Enalapril is an orally-active and long-acting nonsulphydryl antihypertensive agent that suppresses the renin-angiotensin-aldosterone system to lower blood pressure. It was developed from a targeted research programmed using molecular modelling. Being a prodrug, enalapril is rapidly biotransformed into its active metabolite, , which is responsible for the pharmacological actions of enalapril. The active metabolite of enalapril competitively inhibits the ACE to hinder the production of angiotensin II, a key component of the renin-angiotensin-aldosterone system that promotes vasoconstriction and renal reabsorption of sodium ions in the kidneys. Ultimately, Enalapril works to reduce blood pressure and blood fluid volume. Commonly marketed under the trade name Vasotec, enalapril was first approved by the FDA in 1985 for the management of hypertension, heart failure, and asymptomatic left ventricular dysfunction. It is also found in a combination product containing that is used for the management of hypertension. The active metabolite Enalapril is also available in oral tablets and intravenous formulations for injection.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-1-(N-(1-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-prolineChEBI
(S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acidChEBI
1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl esterChEBI
AnalaprilChEBI
EnalaprilaChEBI
EnalaprilumChEBI
(S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylateGenerator
Enalapril maleateHMDB
EnalaprilatHMDB
RenitekHMDB
Maleate, enalaprilHMDB
RenitecHMDB
Chemical FormulaC20H28N2O5
Average Molecular Mass376.447 g/mol
Monoisotopic Mass376.200 g/mol
CAS Registry Number75847-73-3
IUPAC Name(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
Traditional Nameenalapril
SMILESCCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O
InChI IdentifierInChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16-,17-/m0/s1
InChI KeyGBXSMTUPTTWBMN-XIRDDKMYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Proline or derivatives
  • Alpha-amino acid ester
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-acylpyrrolidine
  • Fatty acid ester
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Amino acid
  • Azacycle
  • Secondary aliphatic amine
  • Carboxylic acid
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP0.19ALOGPS
logP0.59ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.67ChemAxon
pKa (Strongest Basic)5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity99.57 m³·mol⁻¹ChemAxon
Polarizability40.41 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4329000000-0ccc991d6f82c8023381Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-4139100000-e739549506767919633fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0809000000-0e192d1573028e60641cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-003r-1859000000-8b202071e8860792a59fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-02ai-0920000000-a43751d817c0f98bc5b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0591000000-1e07b9fe2aaace58211eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-e737fba7359f446dfefaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0096000000-f899a068af97bea539acSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-003r-1859000000-a8e3ac5e4d170e35772cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-02t9-0900000000-0f67eb2d8b2e7821015cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0591000000-9695db764f080d9ae857Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0809000000-0e192d1573028e60641cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0095000000-f899a068af97bea539acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0239000000-feb01e2c02b331eea247Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-5893000000-141cda4f7233f214c8dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0296-6910000000-189f3dddcaf5004e885fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1019000000-ae65ecb00dc3ab6e3701Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03gs-5559000000-d8643ca2f50322b85449Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-8921000000-5383f963d934648ca615Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0129000000-f7705eec0d29efd988c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sl-3944000000-04f3a7836b5b57821688Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0903-3900000000-cb0bc55987e5b9460684Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0109000000-ec7a71512e90259b372cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-3913000000-89b99fdc1118ca034b01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3900000000-294402e5b0098d7dc45eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00584
HMDB IDHMDB0014722
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD0-2065
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEnalapril
Chemspider ID4534998
ChEBI ID4784
PubChem Compound ID40466924
Kegg Compound IDC06977
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. D.P. Ip and G.S. Brenner, in K. Florey (Editor), Analytical Profiles of Drug Substances, Vol. 16, Aca- demic Press, London, 1987, pp. 207-243.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10669559
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23030053
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23413003