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Showing Compound Canrenone (FDB023096)

Record Information
Version1.0
Creation date2011-09-21 00:24:37 UTC
Update date2015-10-09 22:33:19 UTC
Primary IDFDB023096
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCanrenone
DescriptionCanrenone is the major metabolite of spironolactone. Spironolactone is a competitive aldosterone receptor antagonist (ARA), has traditionally been the treatment of first choice in idiopathic hyperaldosteronism (IHA) and for preoperative management of aldosterone producing adenoma (APA), and its therapeutic properties are attributable to active metabolite canrenone. Canrenone and the K+ salt of canrenoate are also in clinical use: they avoid the formation of intermediate products with anti-androgenic and progestational actions, resulting in a decreased incidence of side effects. (PMID: 10790593) [HMDB]
CAS Number976-71-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
3-(3-Oxo-17b-hydroxy-4,6-androstadien-17a-yl)propionic acid g-lactonehmdb
3'-(3-Oxo-17b-hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactonehmdb
Canrenonehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H28O3
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
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
Isomeric 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
Average Molecular Weight340.4559
Monoisotopic Molecular Weight340.203844762
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCanrenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01u0-0294000000-4ef8f41e0a3349fc5759Spectrum
Predicted GC-MSCanrenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-2910000000-895da7d842991e1f26312017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-3900000000-44a9709cabb5e8f1da5d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0079-0962000000-d3aa34556f83b16405c82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05tr-0962000000-924d636ff93f46fb7ccc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-0a4i-3900000000-3a30ad26d169f0f4376d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0079-0952000000-a659329c1d4dbdaa35fd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4j-2910000000-2271fd51503b36f1ecaf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-849841b26aeae34c6f442021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-1519000000-065659f87f49131d9fab2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-fb528a0adb13d3312a172021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-6bba4c38ef31d75b00ec2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-66e37b861f6b28f50cf22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-1619000000-c577e8993bba997d0aab2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-05tr-0962000000-aca4c3d2f6a79f56a8fc2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0069000000-abaf24a61a9edc70752d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rx-0092000000-2761d2c9cf7170266c032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsr-1970000000-540279571f8d029740a12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0029000000-f3a98fb00ac173fe1bf32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-0069000000-c492d9b48fd5165300ce2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5090000000-08c680b27aee962071d42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-0e4e8b92f10e785e2dde2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0943000000-4f159ad08076205f9bef2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03mi-1910000000-72c9aebfc155facc9fb82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-0b542547fa4ff7747c312021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1059000000-1afc199ac4c118cab55c2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID13192
ChEMBL IDCHEMBL1463345
KEGG Compound IDNot Available
Pubchem Compound ID13789
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03033
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCanrenone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference