Enalapril
Athanor · official
C20H28N2O5 · 376.4 g/mol
IUPAC name: (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid
Also called Vasotec, ACE inhibitor
WarningMay cause an allergic skin reaction · Suspected of damaging fertility or the unborn childNames and identifiers
- IUPAC name
- (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid
- Synonyms
- Vasotec, ACE inhibitor, Enalaprila
+ 37 more
Enalaprilum, Bonuten, Olinapril, DTXSID5022982, 69PN84IO1A, C09AA02, (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid, (S)-1-(N-(1-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline, 1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester, CHEBI:4784, DTXCID202982, L-Proline, N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-, (2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid, (S)-1-{(S)-2-[1-((S)-Ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid, L-Proline, N-((1S)-1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl-, Renitek, L-Proline, 1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-, (S)-, (2S)-1-((2S)-2-(((2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)pyrrolidine-2-carboxylic acid, (S)-1-((S)-2-(1-((S)-Ethoxycarbonyl)-3-phenyl-propylamino)-propionyl)-pyrrolidine-2-carboxylic acid, RefChem:6425, 616-271-9, Kinfil, Enalaprilum [INN-Latin], Enalaprila [INN-Spanish], Enalapril (INN), CHEMBL578, N-[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline, NCGC00021569-04, ENALAPRIL [INN], ((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl-L-proline, SCHEMBL18, N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl-L-proline, Enalapril Richet, Gadopril, HSDB 6529, CAS-75847-73-3, Enalapril [INN:BAN]
- Molecular formula
- C20H28N2O5
- Empirical formula
- C20H28N2O5
- Molecular weight
- 376.4 g/mol
- Exact mass
- 376.19982
- CAS number
- 75847-73-3
- PubChem CID
- 5388962
- Canonical SMILES
- CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CCCC2C(=O)O
- Isomeric SMILES
- CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CCC[C@H]2C(=O)O
- InChI
- InChI=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
- InChIKey
- GBXSMTUPTTWBMN-XIRDDKMYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Physical properties
- Solubility in water
- In water, 1.64 × 10⁴ mg/L at 25 °C[1]
- log P
- log Kow = 0.07 at pH 4.9[1]
- pKa
- pKa1 = 3.0 (carboxylic acid)[1]
7 values
Only one source reports it.
Value As written Source –shown pKa1 = 3.0 (carboxylic acid) [1] Hazardous Substances Data Bank (HSDB)cites Loftsson T et al; Acta Ophthalmologica 88(3): 337-41 (2010). Available from, as of Oct 27, 2017: https://onlinelibrary.wiley.com/doi/10.1111/j.1755-3768.2008.01495.x/pdf – pKa2 = 5.5 (secondary amide) [1] Hazardous Substances Data Bank (HSDB)cites Loftsson T et al; Acta Ophthalmologica 88(3): 337-41 (2010). Available from, as of Oct 27, 2017: https://onlinelibrary.wiley.com/doi/10.1111/j.1755-3768.2008.01495.x/pdf – pKa1 = 3 (carboxylic acid) [1] Hazardous Substances Data Bank (HSDB)cites McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1856 – pKa2 = 5.4 (secondary amine), at 25 °C [1] Hazardous Substances Data Bank (HSDB)cites McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2003. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2003 (Plus Supplements)., p. 1856 – pKa1 = 2.3 (carboxylic acid) [1] Hazardous Substances Data Bank (HSDB)cites Loftsson T et al; Acta Ophthalmologica 88(3): 337-41 (2010). Available from, as of Oct 27, 2017: https://onlinelibrary.wiley.com/doi/10.1111/j.1755-3768.2008.01495.x/pdf – pKa2 = 3.4 (caboxylic acid) [1] Hazardous Substances Data Bank (HSDB)cites Loftsson T et al; Acta Ophthalmologica 88(3): 337-41 (2010). Available from, as of Oct 27, 2017: https://onlinelibrary.wiley.com/doi/10.1111/j.1755-3768.2008.01495.x/pdf – pKa3 = 8.0 (secondary amide) /Enalaprilat/ [1] Hazardous Substances Data Bank (HSDB)cites Loftsson T et al; Acta Ophthalmologica 88(3): 337-41 (2010). Available from, as of Oct 27, 2017: https://onlinelibrary.wiley.com/doi/10.1111/j.1755-3768.2008.01495.x/pdf
Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.
Calculated
- Heavy atoms
- 27
- Rings
- 2
- Aromatic rings
- 1
- Fraction sp³ carbons (Fsp3)
- 0.55
- H-bond donors
- 2
- H-bond acceptors
- 5 computed here · PubChem 6
- Rotatable bonds
- 9 computed here · PubChem 10
- TPSA (Ų)
- 95.9
- Formal charge
- 0
- XLogP3
- -0.1 PubChem
- Complexity
- 519 PubChem
- Stereocenters
- 3 definedCIP: C6: S · C16: S · C24: S
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C63.81%
- H7.50%
- N7.44%
- O21.25%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 1.6 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -2.76 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.05 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 376.45
- log P ≤ 5 (Crippen): 1.6
- H-bond donors ≤ 5: 2
- H-bond acceptors ≤ 10: 5
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Warning
Most widely reported: 39 company reports to ECHA. Source [2].
- Harmful or irritant
- Health hazard
- H317May cause an allergic skin reaction
- H361Suspected of damaging fertility or the unborn child
Precautionary statements: P203, P261, P272, P280, P302+P352, P318, P321, P333+P317, P362+P364, P405, P501
Storage
- Commercially available enalaprilat injection should be stored at a temperature less than 30 °C. (enalaprilat)[1]
- The manufacturer recommends that enalapril maleate tablets be stored in tight containers at a temperature <30 °C and that transient exposure to temperatures warmer than 50 °C be avoided. The tablets should be protected from moisture. The tablets have an expiration date of 30 mos following the date of manufacture when stored at <30 °C. The manufacturer states that extemporaneous preparation of oral solutions of enalapril maleate should be avoided since the drug is not sufficiently stable in solution.[1]
- Keep container tightly closed in a dry and well-ventilated place. (enalapril maleate)[1]
Incompatibilities
- Incompatible materials: Strong oxidizing agents. (enalapril maleate)[1]
Safety data sheets on the supplier’s page: AKos Consulting & Solutions, Ambinter, Sigma-Aldrich.
Always read the supplier’s safety data sheet before working with it.
Spectra
- GC-MSSpectraBase
- MS-MSHuman Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive)
- LC-MSMassBank Europe (Exploris 480 Orbitrap (Thermo Scientific) · LC-ESI-QFT · POSITIVE) · MassBank Europe (Exploris 480 Orbitrap (Thermo Scientific) · LC-ESI-QFT · NEGATIVE) · MassBank Europe (Bruker maXis Impact · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker maXis Impact · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker maXis Impact · LC-ESI-QTOF · POSITIVE) · MassBank Europe (Bruker maXis Impact · LC-ESI-QTOF · POSITIVE)
- ATR-IRSpectraBase (Bio-Rad FTS · ATR-Film (MeCl2) (DuraSamplIR II))
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
- [2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [4]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [5]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [6]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [7]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.