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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:27 UTC
Update Date2021-09-14 15:40:02 UTC
HMDB IDHMDB0003033
Secondary Accession Numbers
  • HMDB03033
Metabolite Identification
Common 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 ).
Structure
Data?1582752261
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 Weight340.4559
Monoisotopic Molecular Weight340.203844762
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
CAS Registry Number976-71-6
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 Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.68HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.12931661259
DarkChem[M-H]-175.9731661259
DeepCCS[M-2H]-217.42730932474
DeepCCS[M+Na]+192.38330932474
AllCCS[M+H]+186.632859911
AllCCS[M+H-H2O]+183.832859911
AllCCS[M+NH4]+189.232859911
AllCCS[M+Na]+189.932859911
AllCCS[M-H]-192.632859911
AllCCS[M+Na-2H]-192.732859911
AllCCS[M+HCOO]-193.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Canrenone[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C3800.8Standard polar33892256
Canrenone[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C2815.2Standard non polar33892256
Canrenone[H][C@@]12CC[C@@]3(CCC(=O)O3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C=CC2=CC(=O)CC[C@]12C3292.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Canrenone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](C=CC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@]21CCC(=O)O13127.4Semi standard non polar33892256
Canrenone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](C=CC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@]21CCC(=O)O12924.3Standard non polar33892256
Canrenone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](C=CC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@@]21CCC(=O)O13471.4Standard polar33892256
Canrenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)C=C[C@H]1[C@@H]3CC[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]123368.8Semi standard non polar33892256
Canrenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)C=C[C@H]1[C@@H]3CC[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]123163.3Standard non polar33892256
Canrenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)C=C[C@H]1[C@@H]3CC[C@@]4(CCC(=O)O4)[C@@]3(C)CC[C@@H]123655.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Canrenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-01u0-0294000000-4ef8f41e0a3349fc57592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Canrenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone LC-ESI-ITFT , positive-QTOFsplash10-0a4j-2910000000-895da7d842991e1f26312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone LC-ESI-ITFT , positive-QTOFsplash10-0a4i-3900000000-44a9709cabb5e8f1da5d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone LC-ESI-ITFT , positive-QTOFsplash10-0079-0962000000-d3aa34556f83b16405c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone LC-ESI-ITFT , positive-QTOFsplash10-05tr-0962000000-924d636ff93f46fb7ccc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 80V, Positive-QTOFsplash10-0a4i-3900000000-3a30ad26d169f0f4376d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 35V, Positive-QTOFsplash10-0079-0952000000-a659329c1d4dbdaa35fd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 55V, Positive-QTOFsplash10-0a4j-2910000000-2271fd51503b36f1ecaf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 40V, Positive-QTOFsplash10-0a4i-4900000000-849841b26aeae34c6f442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 20V, Positive-QTOFsplash10-0006-1519000000-065659f87f49131d9fab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 40V, Positive-QTOFsplash10-0a4i-4900000000-fb528a0adb13d3312a172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 10V, Positive-QTOFsplash10-0006-0009000000-6bba4c38ef31d75b00ec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 10V, Positive-QTOFsplash10-0006-0009000000-66e37b861f6b28f50cf22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 20V, Positive-QTOFsplash10-0006-1619000000-c577e8993bba997d0aab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Canrenone 55V, Positive-QTOFsplash10-05tr-0962000000-aca4c3d2f6a79f56a8fc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 10V, Positive-QTOFsplash10-0006-0069000000-abaf24a61a9edc70752d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 20V, Positive-QTOFsplash10-00rx-0092000000-2761d2c9cf7170266c032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 40V, Positive-QTOFsplash10-0fsr-1970000000-540279571f8d029740a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 10V, Negative-QTOFsplash10-000i-0029000000-f3a98fb00ac173fe1bf32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 20V, Negative-QTOFsplash10-000j-0069000000-c492d9b48fd5165300ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 40V, Negative-QTOFsplash10-0006-5090000000-08c680b27aee962071d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 10V, Positive-QTOFsplash10-0006-0009000000-0e4e8b92f10e785e2dde2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 20V, Positive-QTOFsplash10-004l-0943000000-4f159ad08076205f9bef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 40V, Positive-QTOFsplash10-03mi-1910000000-72c9aebfc155facc9fb82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 10V, Negative-QTOFsplash10-000i-0009000000-0b542547fa4ff7747c312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Canrenone 20V, Negative-QTOFsplash10-000i-1059000000-1afc199ac4c118cab55c2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12221
Phenol Explorer Compound IDNot Available
FooDB IDFDB023096
KNApSAcK IDNot Available
Chemspider ID13192
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCanrenone
METLIN IDNot Available
PubChem Compound13789
PDB IDNot Available
ChEBI ID987229
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSkibinska, Maria; Smolinska, Jadwiga; Stochlak, Edward. Method of manufacturing canrenone. Pol. (1994), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:15584083 ]
  2. Mantero F, Lucarelli G: Aldosterone antagonists in hypertension and heart failure. Ann Endocrinol (Paris). 2000 Feb;61(1):52-60. [PubMed:10790593 ]