ChemFOnt: Showing chemical card for Enalaprilat (CFc000022720)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:15:09 UTC

Chemfont ID

CFc000022720

Molecule Identification

Common Name

Enalaprilat

Definition

Enalaprilat belongs to the family of Peptides. 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. Enalaprilat is the active drug form of the ACE inhibitor Enalapril.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Enalapril acid	ChEBI
Enalapril diacid	ChEBI
Enalaprilat anhydrous	ChEBI
Enalaprilate	ChEBI
Enalaprilatum	ChEBI
Enalaprilic acid	Generator
N-[(1S)-1-Carboxy-3-phenylpropyl]-L-alanyl-L-proline	HMDB
Boehringer ingelheim brand OF enalaprilat anhydrous	HMDB
Enalaprilat, (R)-isomer, anhydrous	HMDB
MSD Brand OF enalaprilat	HMDB
Merck frosst brand OF enalaprilat anhydrous	HMDB
Pres IV	HMDB
Anhydrous enalaprilat citrate	HMDB
Dihydrate, enalaprilat	HMDB
Enalapril-teva	HMDB
Enalaprilat dihydrate	HMDB
Vasotec	HMDB
Anhydrous, enalaprilat	HMDB
Biovail brand OF enalaprilat anhydrous	HMDB
Enalapril teva	HMDB
Teva brand OF enalaprilat	HMDB
Xanef	HMDB
EnalaprilTEVA	HMDB
Enalaprilat citrate, anhydrous	HMDB
1-(N-((S)-1-Carboxy-3-phenylpropyl)-L-alanyl)-L-proline dihydrate	HMDB

Chemical Formula

C₁₈H₂₄N₂O₅

Average Molecular Weight

348.3936

Monoisotopic Molecular Weight

348.168521888

IUPAC Name

(2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

enalaprilat

CAS Registry Number

76420-72-9

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 Key

LZFZMUMEGBBDTC-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.

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
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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:4786 )
dicarboxylic acid (CHEBI:4786 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0041886)

Endogenous

Endogenous (HMDB: HMDB0041886)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Enalapril Action Pathway (PathBank: SMP0000148)

Metabolic pathway

Enalapril Metabolism Pathway (PathBank: SMP0000593)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	-1.1	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.94 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	90.06 m³·mol⁻¹	ChemAxon
Polarizability	35.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon