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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:46:05 UTC
Update Date2021-09-14 15:40:14 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. In humans, enalaprilat is involved in the enalapril metabolism pathway. Enalaprilat is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Enalaprilat.
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 dihydrateHMDB
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
Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point148 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.74Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.13931661259
DarkChem[M-H]-175.07931661259
DeepCCS[M+H]+174.80630932474
DeepCCS[M-H]-172.41130932474
DeepCCS[M-2H]-205.29430932474
DeepCCS[M+Na]+180.71930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Enalaprilat[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@@]1([H])C(O)=O4204.0Standard polar33892256
Enalaprilat[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@@]1([H])C(O)=O2729.6Standard non polar33892256
Enalaprilat[H][C@@](C)(N[C@@]([H])(CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@@]1([H])C(O)=O2911.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Enalaprilat,1TMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O2815.5Semi standard non polar33892256
Enalaprilat,1TMS,isomer #2C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C2849.3Semi standard non polar33892256
Enalaprilat,1TMS,isomer #3C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C2817.6Semi standard non polar33892256
Enalaprilat,2TMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C2798.0Semi standard non polar33892256
Enalaprilat,2TMS,isomer #2C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2779.5Semi standard non polar33892256
Enalaprilat,2TMS,isomer #3C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C2804.5Semi standard non polar33892256
Enalaprilat,3TMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2792.6Semi standard non polar33892256
Enalaprilat,3TMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2798.2Standard non polar33892256
Enalaprilat,1TBDMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O3056.7Semi standard non polar33892256
Enalaprilat,1TBDMS,isomer #2C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3100.8Semi standard non polar33892256
Enalaprilat,1TBDMS,isomer #3C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C3086.0Semi standard non polar33892256
Enalaprilat,2TBDMS,isomer #1C[C@H](N[C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C3256.9Semi standard non polar33892256
Enalaprilat,2TBDMS,isomer #2C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3302.9Semi standard non polar33892256
Enalaprilat,2TBDMS,isomer #3C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O)[Si](C)(C)C(C)(C)C3324.3Semi standard non polar33892256
Enalaprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3523.3Semi standard non polar33892256
Enalaprilat,3TBDMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([C@@H](CCC1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3389.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Enalaprilat GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9754000000-3a41d05f9e4234d05b072017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enalaprilat GC-MS (2 TMS) - 70eV, Positivesplash10-072l-9344200000-93935d360082bec206712017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Enalaprilat GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Enalaprilat LC-ESI-qTof , Positive-QTOFsplash10-052b-0249000000-37aae68bb758e513d0fb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Enalaprilat 35V, Positive-QTOFsplash10-0r00-0963000000-939227e388ef8bfcf4322021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 10V, Positive-QTOFsplash10-0f6t-0339000000-c990198638da090503712017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 20V, Positive-QTOFsplash10-0bt9-3952000000-b55bd4a7d2d4f28b8b5d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 40V, Positive-QTOFsplash10-03xu-7910000000-8f95f822bca5cc26f1182017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 10V, Negative-QTOFsplash10-0f6t-0019000000-445a0f1673407760a96a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 20V, Negative-QTOFsplash10-114i-3669000000-2b6b8f356eb1715037642017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 40V, Negative-QTOFsplash10-03xr-6910000000-57cc074642142eb8cf852017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 10V, Negative-QTOFsplash10-03dj-0906000000-2051156f2894ed5c32e32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 20V, Negative-QTOFsplash10-03di-2901000000-a50d16529dc991bea3b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 40V, Negative-QTOFsplash10-03di-5900000000-a96381a2d6bd0e02219f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 10V, Positive-QTOFsplash10-0002-0009000000-69840ed84c1ff195ff0d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 20V, Positive-QTOFsplash10-03di-3911000000-770a457420da28fa81022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Enalaprilat 40V, Positive-QTOFsplash10-02t9-5910000000-7507bca771d5c5ed358b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4575429
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
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available