Captopril (CED0002053)

Record Information
Version1.0
Creation Date2016-05-22 04:23:28 UTC
Update Date2026-05-14 16:58:40 UTC
Accession NumberCHEM017481
Identification
Common NameCaptopril
ClassSmall Molecule
Description
Captopril (C9H15NO3S) is an organic compound with an average molecular weight of 217.28 g/mol. Captopril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. It is used as a biological antioxidant (PMC12841722) and is classified as an ACE inhibitor. Recorded exposure routes for this compound include oral administration. Captopril is found in or released from 15 recorded sources, including healthcare, pharmaceuticals & veterinary products; food, food processing & cookware, such as the preparation of wine or sparkling wine and the preparation of vinegar; household cleaning & consumer products, including other smoking requisites, non electric simulated smoking devices, and cigar cigarettes; and electrical & electronic equipment, including electric switches, electric hearing aids, communication cables or conductors, auxiliary devices, and antennas. The compound interacts with five recorded protein targets, serving as an activator or inhibitor of Angiotensin-converting enzyme (ACE), as well as Leukotriene A-4 hydrolase (LTA4H), Matrix metalloproteinase-9 (MMP9), and 72 kDa type IV collagenase (MMP2). Regarding health effects, Captopril is used as a treatment for hypertension (PMC10888711, PMC9265340, PMC9505973) and chronic kidney disease (PMC12067445). Additionally, it has a therapeutic effect on heart failure (PMC12841722).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acidChEBI
AcepressChEBI
ApoprilChEBI
CapotenChEBI
CaptolaneChEBI
CaptoprilumChEBI
CaptoprylChEBI
CaptorilChEBI
CesplonChEBI
CPChEBI
D-2-Methyl-3-mercaptopropanoyl-L-prolineChEBI
D-3-Mercapto-2-methylpropanoyl-L-prolineChEBI
DilabarChEBI
GarranilChEBI
HypertilChEBI
L-CaptoprilChEBI
LopirinChEBI
TenosbonChEBI
TensobonChEBI
TensoprelChEBI
(2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylateGenerator
(2S)-1-[(2S)-2-Methyl-3-sulphanylpropanoyl]pyrrolidine-2-carboxylateGenerator
(2S)-1-[(2S)-2-Methyl-3-sulphanylpropanoyl]pyrrolidine-2-carboxylic acidGenerator
(S)-1-(3-Mercapto-2-methyl-1-oxopropyl)-L-prolineHMDB
Chemical FormulaC9H15NO3S
Average Molecular Mass217.285 g/mol
Monoisotopic Mass217.077 g/mol
CAS Registry Number62571-86-2
IUPAC Name(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
Traditional Namecaptopril
SMILESC[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O
InChI IdentifierInChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1
InChI KeyFAKRSMQSSFJEIM-RQJHMYQMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Proline or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkylthiol
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organosulfur compound
  • Carbonyl group
  • Organic oxide
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.52 g/LALOGPS
logP1.02ALOGPS
logP0.73ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.63 m³·mol⁻¹ChemAxon
Polarizability21.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-002f-9400000000-51d6dae57d8b305064acNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00fr-9410000000-65f35f9df00d94abb290Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0940000000-26ddf220b67fb8dcdff0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-8797427ebbfead8313f9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0940000000-26ddf220b67fb8dcdff0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-8910000000-d831e8d48402a4c5fe73Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-9720000000-8218e12ef8f7e988c312Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0490000000-368990ca74ad93e14251Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0290000000-1fecd0b4a33bc6afc4f2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-0940000000-089a033b51be30f3a297Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3950000000-02525f49c5ae7c64e751Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9100000000-2d3dff49389d32966270Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-5fec50f211615a61cd58Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9200000000-955e87fa6bbc3b688dc5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-12f0a42fb63fd9a341e4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9100000000-8a3f39d9e1f9e0ddfa3aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-9720000000-cc5d5a56e386ed3da5dfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0910000000-8797427ebbfead8313f9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-4920000000-abe7ab7a43bb4ab37f27Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0390000000-443943c884569fe9bddeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-2950000000-6310d54f5354a953ff47Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0490000000-0eb132088f12eaffb9ddNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3970000000-ec3a19d3e043357c455aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0890000000-6471cadb8251b2cde228Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uk9-3920000000-93e7eef38f7bf8d57f56Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-9400000000-f8b12a12ec76d0508922Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-1930000000-21d83329a778cc965f80Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00yr-2910000000-30e872740f7cb996700dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-015c-9500000000-9c8558c81f9491de8c08Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0390000000-434bf0105c7ac7d85511Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ba-7920000000-3051e7e669f1f7f99084Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-1894bb389f2f602b0eabNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02t9-0970000000-3f1d0bcbf6eb82efb044Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-4910000000-58dac33fc2d4ca8212ddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-9300000000-fdbef1e8452ab592e12eNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2174.0Log mg/kg[1200:3900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypertensionis_treatment_forNot AvailablePMC10888711 , PMC9265340 , PMC9505973
heart failurehas_therapeutic_effect_onNot AvailablePMC12841722
chronic kidney diseaseis_treatment_forNot AvailablePMC12067445
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
295ACE inhibitorsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
602MolluscicidesAgriculture & land managementNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
622Game AccessoriesRecreation & sports surfacesNot Available
627Roulette GamesRecreation & sports surfacesNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAngiotensin-converting enzymeP12822Oryctolagus cuniculusPredicted (SEA)0.622794
Click to view 3D structureSuccinyl-diaminopimelate desuccinylaseP44514Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)Predicted (SEA)0.155698
Click to view 3D structureAngiotensin-converting enzymeP47820Rattus norvegicusPredicted (SEA)0.233548
Angiotensin-converting enzyme structureClick to view 3D structureAngiotensin-converting enzymeP12821HumansPredicted (SEA)1.01204
Click to view 3D structureNeprilysinP08049Oryctolagus cuniculusPredicted (SEA)3.03612
Click to view 3D structureIgA-specific serine endopeptidase autotransporterP09790Neisseria gonorrhoeaePredicted (SEA)0.389246
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)40.7151
Renin structureClick to view 3D structureReninP00797HumansPredicted (SEA)14.0129
Leukotriene A-4 hydrolase structureClick to view 3D structureLeukotriene A-4 hydrolaseP09960HumansPredicted (SEA)6.30579
Diphosphomevalonate decarboxylase structureClick to view 3D structureDiphosphomevalonate decarboxylaseP53602HumansPredicted (SEA)0.311397
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)11.8331
Click to view 3D structureXaa-Pro aminopeptidase 2O43895HumansPredicted (SEA)2.33548
Xaa-Pro dipeptidase structureClick to view 3D structureXaa-Pro dipeptidaseP12955HumansPredicted (SEA)8.25202
Endothelin-converting enzyme 1 structureClick to view 3D structureEndothelin-converting enzyme 1P42892HumansPredicted (SEA)15.9591
Click to view 3D structureXaa-Pro aminopeptidase 2Q99MA2Rattus norvegicusPredicted (SEA)9.34191
Metallo-beta-lactamase type 2 structureClick to view 3D structureMetallo-beta-lactamase type 2C7C422Klebsiella pneumoniaePredicted (SEA)1.24559
Xaa-Pro aminopeptidase 1 structureClick to view 3D structureXaa-Pro aminopeptidase 1Q9NQW7HumansPredicted (SEA)17.5161
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)32.3074
Click to view 3D structureCytosol aminopeptidaseP28838HumansPredicted (SEA)29.2713
Click to view 3D structureBeta-lactamase NDM-1E5KIY2Escherichia coliPredicted (SEA)0.155698
Dipeptidyl peptidase 8 structureClick to view 3D structureDipeptidyl peptidase 8Q6V1X1HumansPredicted (SEA)24.3668
Dipeptidyl peptidase 2 structureClick to view 3D structureDipeptidyl peptidase 2Q9UHL4HumansPredicted (SEA)17.9832
Beta-lactamase structureClick to view 3D structureBeta-lactamaseQ9K2N0Pseudomonas aeruginosaPredicted (SEA)0.467095
Click to view 3D structureMax-like protein XQ9UH92HumansPredicted (SEA)16.1926
Neprilysin structureClick to view 3D structureNeprilysinP08473HumansPredicted (SEA)84.9335
Concentrations
Not Available
External Links
DrugBank IDDB01197
HMDB IDHMDB0015328
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDX8Z
Wikipedia LinkCaptopril
Chemspider ID40130
ChEBI ID3380
PubChem Compound ID44093
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Atkinson AB, Robertson JI: Captopril in the treatment of clinical hypertension and cardiac failure. Lancet. 1979 Oct 20;2(8147):836-9.
2. Patchett AA, Harris E, Tristram EW, Wyvratt MJ, Wu MT, Taub D, Peterson ER, Ikeler TJ, ten Broeke J, Payne LG, Ondeyka DL, Thorsett ED, Greenlee WJ, Lohr NS, Hoffsommer RD, Joshua H, Ruyle WV, Rothrock JW, Aster SD, Maycock AL, Robinson FM, Hirschmann R, Sweet CS, Ulm EH, Gross DM, Vassil TC, Stone CA: A new class of angiotensin-converting enzyme inhibitors. Nature. 1980 Nov 20;288(5788):280-3.
3. Smith CG, Vane JR: The discovery of captopril. FASEB J. 2003 May;17(8):788-9.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23137627
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23161035
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23278692
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23299024
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23328620
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23397376
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23410042
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23422724
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23429803
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23435971
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=2420897