Canrenone (CHEM018648)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:25:07 UTC
Update Date2016-11-09 01:15:50 UTC
Accession NumberCHEM018648
Identification
Common NameCanrenone
ClassSmall Molecule
DescriptionCanrenone has been used in trials studying the diagnostic of Heart Failure.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
AldadieneMeSH
PhanuraneMeSH
R.P., 11614MeSH
SC-9376CanrenoneChEMBL, HMDB
17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid g-lactoneHMDB
17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid lactoneHMDB
17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactoneHMDB
17b-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acidHMDB
20-Spiroxa-4,6-diene-3,21-dioneHMDB
3'-(3-oxo-17b-Hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactoneHMDB
3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid g-lactoneHMDB
3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid lactoneHMDB
3-(3-oxo-17b-Hydroxy-4,6-androstadien-17a-yl)propionic acid g-lactoneHMDB
Chemical FormulaC22H28O3
Average Molecular Mass340.456 g/mol
Monoisotopic Mass340.204 g/mol
CAS Registry Number976-71-6
IUPAC Name(1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione
Traditional Name(1'S,2R,2'R,10'R,11'S,15'S)-2',15'-dimethylspiro[oxolane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-6',8'-diene-5,5'-dione
SMILES[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C22H28O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h3-4,13,16-18H,5-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1
InChI KeyUJVLDDZCTMKXJK-WNHSNXHDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentSteroid lactones
Alternative Parents
Substituents
  • Steroid lactone
  • 3-oxosteroid
  • Oxosteroid
  • Cyclohexenone
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0042 g/LALOGPS
logP2.79ALOGPS
logP3.6ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)19.94ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity97.48 m³·mol⁻¹ChemAxon
Polarizability38.67 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01u0-0294000000-4ef8f41e0a3349fc5759Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-2910000000-895da7d842991e1f2631Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-3900000000-44a9709cabb5e8f1da5dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0079-0962000000-d3aa34556f83b16405c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05tr-0962000000-924d636ff93f46fb7cccSpectrum
LC-MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-0a4i-3900000000-3a30ad26d169f0f4376dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0079-0952000000-a659329c1d4dbdaa35fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4j-2910000000-2271fd51503b36f1ecafSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-849841b26aeae34c6f44Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-1519000000-065659f87f49131d9fabSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-fb528a0adb13d3312a17Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-6bba4c38ef31d75b00ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-66e37b861f6b28f50cf2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-1619000000-c577e8993bba997d0aabSpectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-05tr-0962000000-aca4c3d2f6a79f56a8fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0069000000-abaf24a61a9edc70752dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rx-0092000000-2761d2c9cf7170266c03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsr-1970000000-540279571f8d029740a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0029000000-f3a98fb00ac173fe1bf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-0069000000-c492d9b48fd5165300ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5090000000-08c680b27aee962071d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-0e4e8b92f10e785e2ddeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0943000000-4f159ad08076205f9befSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03mi-1910000000-72c9aebfc155facc9fb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-0b542547fa4ff7747c31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1059000000-1afc199ac4c118cab55cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDDB12221
HMDB IDHMDB0003033
FooDB IDFDB023096
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCanrenone
Chemspider ID13192
ChEBI ID987229
PubChem Compound ID13789
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Skibinska, Maria; Smolinska, Jadwiga; Stochlak, Edward. Method of manufacturing canrenone. Pol. (1994), 4 pp.
2. Skibinska, Maria; Smolinska, Jadwiga; Stochlak, Edward. Method of manufacturing canrenone. Pol. (1994), 4 pp.
3. Deventer K, Van Eenoo P, Delbeke FT: Simultaneous determination of beta-blocking agents and diuretics in doping analysis by liquid chromatography/mass spectrometry with scan-to-scan polarity switching. Rapid Commun Mass Spectrom. 2005;19(2):90-8.
4. Mantero F, Lucarelli G: Aldosterone antagonists in hypertension and heart failure. Ann Endocrinol (Paris). 2000 Feb;61(1):52-60.