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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:46:05 UTC
Update Date2019-07-23 06:35:11 UTC
HMDB IDHMDB0041886
Secondary Accession Numbers
  • HMDB41886
Metabolite Identification
Common NameEnalaprilat
DescriptionEnalaprilat, also known as enalapril acid or enalapril-teva, 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. Enalaprilat is a very strong basic compound (based on its pKa). In humans, enalaprilat is involved in enalapril action pathway. Enalaprilat is the active metabolite of the orally available pro-drug, enalapril. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. However, for the recommended dose, the duration of action in most patients is approximately six hours. Rarer adverse effects that are less likely, but should be monitored for, include development of anaphylaxis, hypotension, agranulocytosis, hepatic failure, hyperkalemia, and persistent cough. Angioedema associated with laryngeal edema may be fatal.
Structure
Data?1563863711
Synonyms
ValueSource
Enalapril acidChEBI
Enalapril diacidChEBI
Enalaprilat anhydrousChEBI
EnalaprilateChEBI
EnalaprilatumChEBI
Enalaprilic acidGenerator
N-[(1S)-1-Carboxy-3-phenylpropyl]-L-alanyl-L-prolineHMDB
Boehringer ingelheim brand OF enalaprilat anhydrousHMDB
Enalaprilat, (R)-isomer, anhydrousHMDB
MSD Brand OF enalaprilatHMDB
Merck frosst brand OF enalaprilat anhydrousHMDB
Pres IVHMDB
Anhydrous enalaprilat citrateHMDB
Dihydrate, enalaprilatHMDB
Enalapril-tevaHMDB
Enalaprilat dihydrateHMDB
VasotecHMDB
Anhydrous, enalaprilatHMDB
Biovail brand OF enalaprilat anhydrousHMDB
Enalapril tevaHMDB
Teva brand OF enalaprilatHMDB
XanefHMDB
EnalaprilTEVAHMDB
Enalaprilat citrate, anhydrousHMDB
1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline dihydrateMeSH
Chemical FormulaC18H24N2O5
Average Molecular Weight348.3936
Monoisotopic Molecular Weight348.168521888
IUPAC Name(2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid
Traditional Nameenalaprilat
CAS Registry Number76420-72-9
SMILES
[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@@]1([H])C(O)=O
InChI Identifier
InChI=1S/C18H24N2O5/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25)/t12-,14-,15-/m0/s1
InChI KeyLZFZMUMEGBBDTC-QEJZJMRPSA-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
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Secondary amine
  • Azacycle
  • Carboxylic acid
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.74Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.88 g/LALOGPS
logP-0.09ALOGPS
logP-1.1ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)7.83ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.94 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity90.06 m³·mol⁻¹ChemAxon
Polarizability35.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9754000000-3a41d05f9e4234d05b07Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-072l-9344200000-93935d360082bec20671Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-052b-0249000000-37aae68bb758e513d0fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-0339000000-c990198638da09050371Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-3952000000-b55bd4a7d2d4f28b8b5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-7910000000-8f95f822bca5cc26f118Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0019000000-445a0f1673407760a96aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114i-3669000000-2b6b8f356eb171503764Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xr-6910000000-57cc074642142eb8cf85Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09477
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5292946
KEGG Compound IDC11720
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEnalaprilat
METLIN IDNot Available
PubChem Compound6917719
PDB IDEAL
ChEBI ID4786
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available