Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2006-05-22 15:12:27 UTC
Updated at2021-10-07 20:40:55 UTC
NP-MRD IDNP0000985
Secondary Accession NumbersNone
Natural Product 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
Thumb
Synonyms
ValueSource
SC-9376CanrenoneHMDB
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
AldadieneHMDB
PhanuraneHMDB
R.P., 11614HMDB
Chemical FormulaC22H28O3
Average Mass340.4559 Da
Monoisotopic Mass340.20384 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.68Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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
HMDB IDHMDB0003033
DrugBank IDDB12221
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  3. Tatipalli M, Siripuram VK, Long T, Shuster D, Bernstein G, Martineau P, Cook KA, Cristofoletti R, Schmidt S, Vozmediano V: Model-Informed Optimization of a Pediatric Clinical Pharmacokinetic Trial of a New Spironolactone Liquid Formulation. Pharmaceutics. 2021 Jun 8;13(6). pii: pharmaceutics13060849. doi: 10.3390/pharmaceutics13060849. [PubMed:34201093 ]
  4. Dahmana N, Mugnier T, Gabriel D, Favez T, Kowalczuk L, Behar-Cohen F, Gurny R, Kalia YN: Polymeric micelle mediated follicular delivery of spironolactone: Targeting the mineralocorticoid receptor to prevent glucocorticoid-induced activation and delayed cutaneous wound healing. Int J Pharm. 2021 Jul 15;604:120773. doi: 10.1016/j.ijpharm.2021.120773. Epub 2021 Jun 4. [PubMed:34090990 ]
  5. Young MJ, Kanki M, Karthigan N, Konstandopoulos P: The role of the mineralocorticoid receptor and mineralocorticoid-receptor-directed therapies in heart failure. Endocrinology. 2021 May 29. pii: 6288445. doi: 10.1210/endocr/bqab105. [PubMed:34050730 ]
  6. Cha J, Hong S, Lee J, Gwak J, Kim M, Kim T, Hur J, Giesy JP, Khim JS: Novel polar AhR-active chemicals detected in sediments of an industrial area using effect-directed analysis based on in vitro bioassays with full-scan high resolution mass spectrometric screening. Sci Total Environ. 2021 Jul 20;779:146566. doi: 10.1016/j.scitotenv.2021.146566. Epub 2021 Mar 17. [PubMed:34030261 ]
  7. Rong S, Tang X, Guan S, Zhang B, Li Q, Cai B, Huang J: Effects of Impeller Geometry on the 11alpha-Hydroxylation of Canrenone in Rushton Turbine-Stirred Tanks. J Microbiol Biotechnol. 2021 Jun 28;31(6):890-901. doi: 10.4014/jmb.2104.04002. [PubMed:34024892 ]
  8. Radloff J, Pagitz M, Andrukhova O, Oberbauer R, Burgener IA, Erben RG: Aldosterone Is Positively Associated With Circulating FGF23 Levels in Chronic Kidney Disease Across Four Species, and May Drive FGF23 Secretion Directly. Front Physiol. 2021 Apr 29;12:649921. doi: 10.3389/fphys.2021.649921. eCollection 2021. [PubMed:33995120 ]
  9. Pecori A, Buffolo F, Burrello J, Mengozzi G, Rumbolo F, Avataneo V, D'Avolio A, Rabbia F, Bertello C, Veglio F, Mulatero P, Monticone S: Mineralocorticoid Receptor Antagonist Effect on Aldosterone to Renin Ratio in Patients With Primary Aldosteronism. J Clin Endocrinol Metab. 2021 Aug 18;106(9):e3655-e3664. doi: 10.1210/clinem/dgab290. [PubMed:33942084 ]
  10. Wagmann L, Vollmer AC, Lauder L, Mahfoud F, Meyer MR: Assessing Adherence to Antihypertensive Medication by Means of Dose-Dependent Reference Plasma Concentration Ranges and Ultra-High Performance Liquid Chromatography-Ion Trap Mass Spectrometry Analysis. Molecules. 2021 Mar 9;26(5). pii: molecules26051495. doi: 10.3390/molecules26051495. [PubMed:33803489 ]
  11. Bernhardt R, Neunzig J: Underestimated reactions and regulation patterns of adrenal cytochromes P450. Mol Cell Endocrinol. 2021 Jun 15;530:111237. doi: 10.1016/j.mce.2021.111237. Epub 2021 Mar 13. [PubMed:33722664 ]