Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:24:37 UTC |
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Update date | 2015-10-09 22:33:19 UTC |
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Primary ID | FDB023096 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Canrenone |
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Description | Canrenone 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] |
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CAS Number | 976-71-6 |
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Structure | |
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Synonyms | Synonym | Source |
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Aldadiene | MeSH | Phanurane | MeSH | R.P., 11614 | MeSH | SC-9376Canrenone | ChEMBL, HMDB | 17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid g-lactone | HMDB | 17-Hydroxy-3-oxo-17a-pregna-4,6-diene-21-carboxylic acid lactone | HMDB | 17a-(2-Carboxyethyl)-17b-hydroxyandrosta-4,6-dien-3-one lactone | HMDB | 17b-Hydroxy-3-oxopregna-4,6-diene-21-carboxylic acid | HMDB | 20-Spiroxa-4,6-diene-3,21-dione | HMDB | 3'-(3-oxo-17b-Hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactone | HMDB | 3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid g-lactone | HMDB | 3-(17b-Hydroxy-3-oxoandrosta-4,6-dien-17a-yl)propionic acid lactone | HMDB | 3-(3-oxo-17b-Hydroxy-4,6-androstadien-17a-yl)propionic acid g-lactone | HMDB | 3-(3-Oxo-17b-hydroxy-4,6-androstadien-17a-yl)propionic acid g-lactone | hmdb | 3'-(3-Oxo-17b-hydroxyandrosta-4,6-dien-17a-yl)-propionic acid lactone | hmdb | Canrenone | hmdb |
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Predicted Properties | |
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Chemical Formula | C22H28O3 |
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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 |
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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 |
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InChI Key | UJVLDDZCTMKXJK-WNHSNXHDSA-N |
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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 |
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Average Molecular Weight | 340.4559 |
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Monoisotopic Molecular Weight | 340.203844762 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid lactones |
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Direct Parent | Steroid lactones |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Canrenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01u0-0294000000-4ef8f41e0a3349fc5759 | Spectrum | Predicted GC-MS | Canrenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4j-2910000000-895da7d842991e1f2631 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-3900000000-44a9709cabb5e8f1da5d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0079-0962000000-d3aa34556f83b16405c8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-05tr-0962000000-924d636ff93f46fb7ccc | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 80V, Positive | splash10-0a4i-3900000000-3a30ad26d169f0f4376d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0079-0952000000-a659329c1d4dbdaa35fd | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 55V, Positive | splash10-0a4j-2910000000-2271fd51503b36f1ecaf | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-4900000000-849841b26aeae34c6f44 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-1519000000-065659f87f49131d9fab | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-4900000000-fb528a0adb13d3312a17 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0009000000-6bba4c38ef31d75b00ec | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0009000000-66e37b861f6b28f50cf2 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-1619000000-c577e8993bba997d0aab | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 55V, Positive | splash10-05tr-0962000000-aca4c3d2f6a79f56a8fc | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0069000000-abaf24a61a9edc70752d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00rx-0092000000-2761d2c9cf7170266c03 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fsr-1970000000-540279571f8d029740a1 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0029000000-f3a98fb00ac173fe1bf3 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000j-0069000000-c492d9b48fd5165300ce | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-5090000000-08c680b27aee962071d4 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0009000000-0e4e8b92f10e785e2dde | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004l-0943000000-4f159ad08076205f9bef | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03mi-1910000000-72c9aebfc155facc9fb8 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0009000000-0b542547fa4ff7747c31 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1059000000-1afc199ac4c118cab55c | 2021-09-23 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 13192 |
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ChEMBL ID | CHEMBL1463345 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 13789 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB03033 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Canrenone |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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