Enalapril (CED0002046)

Record Information

Version

1.0

Creation Date

2016-05-22 03:40:27 UTC

Update Date

2026-08-20 06:30:26 UTC

Accession Number

CHEM016685

Identification

Common Name

Enalapril

Class

Small Molecule

Description

Enalapril is an organic compound with the formula C20H28N2O5 and an average molecular weight of 376.45 g/mol. Enalapril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. It acts as an inhibitor of the protein target Angiotensin-converting enzyme (ACE). The compound is found in or released from three recorded sources: antennas in electrical and electronic equipment, drinking water in drinking water and water supply, and ACE inhibitors in healthcare, pharmaceuticals, and veterinary products. The recorded exposure route for this substance is oral.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-1-(N-(1-(Ethoxycarbonyl)-3-phenylpropyl)-L-alanyl)-L-proline	ChEBI
(S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylic acid	ChEBI
1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline 1'-ethyl ester	ChEBI
Analapril	ChEBI
Enalaprila	ChEBI
Enalaprilum	ChEBI
(S)-1-{(S)-2-[1-((S)-ethoxycarbonyl)-3-phenyl-propylamino]-propionyl}-pyrrolidine-2-carboxylate	Generator
Enalapril maleate	HMDB
Enalaprilat	HMDB
Renitek	HMDB
Maleate, enalapril	HMDB
Renitec	HMDB

Chemical Formula

C₂₀H₂₈N₂O₅

Average Molecular Mass

376.447 g/mol

Monoisotopic Mass

376.200 g/mol

CAS Registry Number

75847-73-3

IUPAC Name

(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

enalapril

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

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

InChI Key

GBXSMTUPTTWBMN-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid monoester (CHEBI:4784 )
dipeptide (CHEBI:4784 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	0.19	ALOGPS
logP	0.59	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.94 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	99.57 m³·mol⁻¹	ChemAxon
Polarizability	40.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0udi-4329000000-0ccc991d6f82c8023381	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-004i-4139100000-e739549506767919633f	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0809000000-0e192d1573028e60641c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-003r-1859000000-8b202071e8860792a59f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-02ai-0920000000-a43751d817c0f98bc5b6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0591000000-1e07b9fe2aaace58211e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0009000000-e737fba7359f446dfefa	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0096000000-f899a068af97bea539ac	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-003r-1859000000-a8e3ac5e4d170e35772c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-02t9-0900000000-0f67eb2d8b2e7821015c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0591000000-9695db764f080d9ae857	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0809000000-0e192d1573028e60641c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0095000000-f899a068af97bea539ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0059-0239000000-feb01e2c02b331eea247	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-5893000000-141cda4f7233f214c8dc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0296-6910000000-189f3dddcaf5004e885f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-1019000000-ae65ecb00dc3ab6e3701	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03gs-5559000000-d8643ca2f50322b85449	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01ot-8921000000-5383f963d934648ca615	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0129000000-f7705eec0d29efd988c2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01sl-3944000000-04f3a7836b5b57821688	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0903-3900000000-cb0bc55987e5b9460684	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0109000000-ec7a71512e90259b372c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-3913000000-89b99fdc1118ca034b01	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-3900000000-294402e5b0098d7dc45e	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
5710.0	Log mg/kg	[3200:10000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
115	Drinking water	Drinking water & water supply	Not Available
295	ACE inhibitors	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available

Pathways

4 pathways

Enalapril Action Pathway

Enalapril Metabolism Pathway

Enalapril ACE Inhibitor Action Pathway

Enalapril Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Angiotensin-converting enzyme	P12822	Oryctolagus cuniculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Angiotensin-converting enzyme	P12821	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Angiotensin-converting enzyme	P47820	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Angiotensin-converting enzyme 2	Q5EGZ1	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Neprilysin	P08049	Oryctolagus cuniculus	Predicted (SEA)	6.77288
Click to view 3D structure	Renin	P00797	Humans	Predicted (SEA)	15.1027
Click to view 3D structure	Neprilysin	P07861	Rattus norvegicus	Predicted (SEA)	5.60514
Click to view 3D structure	Angiotensin-converting enzyme	P09470	Mus musculus	Predicted (SEA)	0.311397
Click to view 3D structure	Prolyl endopeptidase	P23687	Sus scrofa	Predicted (SEA)	2.33548
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	176.173
Click to view 3D structure	Xaa-Pro aminopeptidase 1	Q9NQW7	Humans	Predicted (SEA)	6.07224
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	201.007
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	163.406
Click to view 3D structure	Prolyl endopeptidase	Q9XTA2	Bos taurus	Predicted (SEA)	2.02408
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	146.746
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	92.407
Click to view 3D structure	FK506 binding protein 12	Q8QGU2	Gallus gallus	Predicted (SEA)	1.55698
Click to view 3D structure	Xaa-Pro aminopeptidase 2	Q99MA2	Rattus norvegicus	Predicted (SEA)	4.12601
Click to view 3D structure	Prolyl endopeptidase	Q9QUR6	Mus musculus	Predicted (SEA)	1.24559
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	178.742
Click to view 3D structure	Breast cancer type 1 susceptibility protein	P38398	Humans	Predicted (SEA)	15.1806
Click to view 3D structure	Prolyl endopeptidase	P27028	Elizabethkingia meningoseptica	Predicted (SEA)	2.33548
Click to view 3D structure	Xaa-Pro aminopeptidase 2	O43895	Humans	Predicted (SEA)	3.50322
Click to view 3D structure	Xaa-Pro dipeptidase	P12955	Humans	Predicted (SEA)	7.62922
Click to view 3D structure	Substance-P receptor	P14600	Rattus norvegicus	Predicted (SEA)	88.7481