Showing metabocard for Canrenone (BMDB0003033)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:02:30 UTC
Update Date2020-04-22 15:11:38 UTC
BMDB IDBMDB0003033
Secondary Accession Numbers
  • BMDB03033
Metabolite Identification
Common NameCanrenone
DescriptionCanrenone, also known as aldadiene or phanurane, belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Based on a literature review a significant number of articles have been published on Canrenone.
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.68HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01u0-0294000000-4ef8f41e0a3349fc5759View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-2910000000-895da7d842991e1f2631View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-3900000000-44a9709cabb5e8f1da5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0079-0962000000-d3aa34556f83b16405c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05tr-0962000000-924d636ff93f46fb7cccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 80V, Positivesplash10-0a4i-3900000000-3a30ad26d169f0f4376dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0079-0952000000-a659329c1d4dbdaa35fdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-0a4j-2910000000-2271fd51503b36f1ecafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-849841b26aeae34c6f44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-1519000000-065659f87f49131d9fabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-fb528a0adb13d3312a17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-6bba4c38ef31d75b00ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-66e37b861f6b28f50cf2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-1619000000-c577e8993bba997d0aabView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-05tr-0962000000-aca4c3d2f6a79f56a8fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0069000000-abaf24a61a9edc70752dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rx-0092000000-2761d2c9cf7170266c03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsr-1970000000-540279571f8d029740a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0029000000-f3a98fb00ac173fe1bf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-0069000000-c492d9b48fd5165300ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5090000000-08c680b27aee962071d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-0e4e8b92f10e785e2ddeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0943000000-4f159ad08076205f9befView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03mi-1910000000-72c9aebfc155facc9fb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-0b542547fa4ff7747c31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1059000000-1afc199ac4c118cab55cView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003033
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
References
Synthesis ReferenceSkibinska, Maria; Smolinska, Jadwiga; Stochlak, Edward. Method of manufacturing canrenone. Pol. (1994), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available