Zofenopril (CED0009586)

Record Information

Version

1.0

Creation Date

2016-05-22 05:51:16 UTC

Update Date

2026-08-21 22:08:55 UTC

SynCED ID

CED0009586

Secondary Accession Numbers

CHEM019142

Identification

Common Name

Zofenopril

Class

Small Molecule

Description

Zofenopril is an organic compound with the formula C22H23NO4S2 and an average molecular weight of 429.55 g/mol. Zofenopril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. In terms of biological activity, it acts as an inhibitor of Angiotensin-converting enzyme (ACE). Regarding its environmental presence, it has been recorded as being found in or released from electrical and electronic equipment, specifically still video cameras.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Zofenoprilum	ChEBI
Zofenil	Kegg
Menarini brand OF zofenopril	MeSH
Zofenopril, calcium salt, (1(r*),2alpha,4alpha)-isomer	MeSH
Zofil	MeSH

Chemical Formula

C₂₂H₂₃NO₄S₂

Average Molecular Mass

429.550 g/mol

Monoisotopic Mass

429.107 g/mol

CAS Registry Number

81872-10-8

IUPAC Name

(2S,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid

Traditional Name

zofenopril

SMILES

[H][C@@](C)(CSC(=O)C1=CC=CC=C1)C(=O)N1C[C@]([H])(C[C@@]1([H])C(O)=O)SC1=CC=CC=C1

InChI Identifier

InChI=1S/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1

InChI Key

IAIDUHCBNLFXEF-MNEFBYGVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol ethers

Alternative Parents

Substituents

Phenoxy compound
Phenol ether
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Monocyclic benzene moiety
Aryl halide
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:31183 )
monocarboxylic acid (CHEBI:31183 )
monochlorobenzenes (CHEBI:31183 )

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

EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (PMC5406448 )?

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	0.0031 g/L	ALOGPS
logP	3.64	ALOGPS
logP	4.31	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.68 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	116.82 m³·mol⁻¹	ChemAxon
Polarizability	44.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0089-0579600000-405ba1e8f207383de142	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1951100000-5672e60650b66e2f4d8c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2940000000-5f3a4da1e3fba25e3d45	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fir-1639300000-a769d55cfbb7e5ce0280	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a6r-1943100000-63f5b38ab4b20904071c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pb9-0910000000-7e6c6df29c1047622f07	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2080.0 Log mg/kg [1200:3700]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
cough	Associated With?	Not Available	A sudden, often repetitive, spasmodic contraction of the thoracic cavity, resulting in violent release of air from the lungs and usually accompanied by a distinctive sound. (NCI CTCAE)	PMC5406448
Isolated systolic hypertension	Not Available	Not Available	Not Available	PMC5406448

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000534	Still Video Cameras?Still video cameras, which capture images in digital format, can be a source of synthetic chemical contamination due to the materials and components used in their production and operation.	Electrical & Electronic Equipment	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Zofenopril Action Pathway

Zofenopril Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Angiotensin-converting enzyme	P47820	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.396 Applicability Domain 0.712 Statistical Significance 7.40e-04 Supporting Reference Compounds 24 E-value 5.76084
Click to view 3D structure	Angiotensin-converting enzyme	P12822	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.396 Applicability Domain 0.712 Statistical Significance 0.0011 Supporting Reference Compounds 26 E-value 8.48557
Click to view 3D structure	Angiotensin-converting enzyme	P12821	Humans	Predicted (SEA)	Prediction Confidence Score 0.334 Applicability Domain 0.391 Statistical Significance 0.0088 Supporting Reference Compounds 46 E-value 68.5852
Click to view 3D structure	Neprilysin	P07861	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.295 Applicability Domain 0.391 Statistical Significance 0.0127 Supporting Reference Compounds 38 E-value 98.7128
Click to view 3D structure	Neprilysin	P08049	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.273 Applicability Domain 0.3 Statistical Significance 0.0225 Supporting Reference Compounds 34 E-value 175.161
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.3 Statistical Significance 0.1227 Supporting Reference Compounds 331 E-value 955.054
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.248 Applicability Domain 0.274 Low confidence Statistical Significance 0.0714 Supporting Reference Compounds 203 E-value 555.766
Click to view 3D structure	Chemokine receptor	Q9MYJ9	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.247 Applicability Domain 0.247 Low confidence Statistical Significance 0.0158 Supporting Reference Compounds 1 E-value 122.768
Click to view 3D structure	Angiotensin-converting enzyme 2	Q5EGZ1	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.245 Applicability Domain 0.329 Statistical Significance 0.0074 Supporting Reference Compounds 2 E-value 57.3749
Click to view 3D structure	Neprilysin	P08473	Humans	Predicted (SEA)	Prediction Confidence Score 0.243 Applicability Domain 0.292 Low confidence Statistical Significance 0.0446 Supporting Reference Compounds 51 E-value 347.363
Click to view 3D structure	Renin	P00797	Humans	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.329 Statistical Significance 0.0451 Supporting Reference Compounds 59 E-value 351.489
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.25 Low confidence Statistical Significance 0.1347 Supporting Reference Compounds 297 E-value 1048.94
Click to view 3D structure	Prothrombin	P00735	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.239 Applicability Domain 0.258 Low confidence Statistical Significance 0.0656 Supporting Reference Compounds 73 E-value 510.457
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.238 Applicability Domain 0.25 Low confidence Statistical Significance 0.6852 Supporting Reference Compounds 1498 E-value 5334.15
Click to view 3D structure	Acetylcholine-binding protein	P58154	Lymnaea stagnalis	Predicted (SEA)	Prediction Confidence Score 0.236 Applicability Domain 0.274 Low confidence Statistical Significance 0.0099 Supporting Reference Compounds 20 E-value 77.3043
Click to view 3D structure	Angiotensin-converting enzyme	P09470	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.236 Applicability Domain 0.329 Statistical Significance 0.0132 Supporting Reference Compounds 4 E-value 102.917
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	Prediction Confidence Score 0.23 Applicability Domain 0.263 Low confidence Statistical Significance 0.2881 Supporting Reference Compounds 427 E-value 2243.15
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	Prediction Confidence Score 0.23 Applicability Domain 0.263 Low confidence Statistical Significance 0.3642 Supporting Reference Compounds 527 E-value 2835.58
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	Prediction Confidence Score 0.229 Applicability Domain 0.263 Low confidence Statistical Significance 0.3953 Supporting Reference Compounds 532 E-value 3077.22
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.228 Applicability Domain 0.244 Low confidence Statistical Significance 0.5181 Supporting Reference Compounds 1103 E-value 4033.68
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.228 Applicability Domain 0.241 Low confidence Statistical Significance 0.7854 Supporting Reference Compounds 1538 E-value 6114.28
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P08483	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.228 Applicability Domain 0.237 Low confidence Statistical Significance 0.0349 Supporting Reference Compounds 55 E-value 271.382
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.228 Applicability Domain 0.263 Low confidence Statistical Significance 0.1386 Supporting Reference Compounds 229 E-value 1079.38
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P08482	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.228 Applicability Domain 0.237 Low confidence Statistical Significance 0.0968 Supporting Reference Compounds 109 E-value 753.736
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P10980	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.227 Applicability Domain 0.237 Low confidence Statistical Significance 0.061 Supporting Reference Compounds 98 E-value 474.958