Zofenopril (CHEM019142)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:51:16 UTC
Update Date2026-04-14 19:19:13 UTC
Accession NumberCHEM019142
Identification
Common NameZofenopril
ClassSmall Molecule
DescriptionA proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-3-(benzoylsulfanyl)-2-methylpropanoyl group. A prodrug for zofenoprilat.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ZofenoprilumChEBI
ZofenilKegg
Menarini brand OF zofenoprilMeSH
Zofenopril, calcium salt, (1(r*),2alpha,4alpha)-isomerMeSH
ZofilMeSH
Chemical FormulaC22H23NO4S2
Average Molecular Mass429.550 g/mol
Monoisotopic Mass429.107 g/mol
CAS Registry Number81872-10-8
IUPAC Name(2S,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid
Traditional Namezofenopril
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 IdentifierInChI=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 KeyIAIDUHCBNLFXEF-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP3.64ALOGPS
logP4.31ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.68 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity116.82 m³·mol⁻¹ChemAxon
Polarizability44.25 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0089-0579600000-405ba1e8f207383de142Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1951100000-5672e60650b66e2f4d8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2940000000-5f3a4da1e3fba25e3d45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fir-1639300000-a769d55cfbb7e5ce0280Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-1943100000-63f5b38ab4b20904071cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-0910000000-7e6c6df29c1047622f07Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13166
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZofenopril
Chemspider IDNot Available
ChEBI ID78539
PubChem Compound ID92400
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21377823
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21394524
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21888941
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22090052
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22107891
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22162922
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22455094
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22707187
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23030285
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23096377
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23552127
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23582628
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23882152
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24211724
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24415271
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24501330
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24583202
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24935917