Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 15:56:34 UTC |
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Update Date | 2021-09-26 23:11:12 UTC |
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HMDB ID | HMDB0255934 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide |
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Description | Oleandrigenin belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Oleandrigenin is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). 16-(acetyloxy)-3,14-dihydroxycard-20(22)-enolide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | CC(=O)OC1CC2(O)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 InChI=1S/C25H36O6/c1-14(26)31-20-12-25(29)19-5-4-16-11-17(27)6-8-23(16,2)18(19)7-9-24(25,3)22(20)15-10-21(28)30-13-15/h10,16-20,22,27,29H,4-9,11-13H2,1-3H3 |
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Synonyms | Value | Source |
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3 alpha,14-Dihydroxy-16 beta-acetoxy-5 beta,14 beta- card-20(22)-enolide | MeSH | 5,11-Dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetic acid | Generator | 5,11-Dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadecan-13-yl acetic acid | Generator |
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Chemical Formula | C25H36O6 |
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Average Molecular Weight | 432.557 |
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Monoisotopic Molecular Weight | 432.251188879 |
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IUPAC Name | 5,11-dihydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate |
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Traditional Name | 5,11-dihydroxy-2,15-dimethyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)OC1CC2(O)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 |
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InChI Identifier | InChI=1S/C25H36O6/c1-14(26)31-20-12-25(29)19-5-4-16-11-17(27)6-8-23(16,2)18(19)7-9-24(25,3)22(20)15-10-21(28)30-13-15/h10,16-20,22,27,29H,4-9,11-13H2,1-3H3 |
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InChI Key | IWCNCUVTGOMGKG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. |
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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 | Cardenolides and derivatives |
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Alternative Parents | |
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Substituents | - Cardanolide-skeleton
- Steroid ester
- 3-hydroxysteroid
- 14-hydroxysteroid
- Hydroxysteroid
- 2-furanone
- Dicarboxylic acid or derivatives
- Cyclic alcohol
- Dihydrofuran
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Tertiary alcohol
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3703.7 | Semi standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3347.3 | Standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 4164.1 | Standard polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TMS,isomer #2 | CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3664.3 | Semi standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TMS,isomer #2 | CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3382.2 | Standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TMS,isomer #2 | CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 4205.8 | Standard polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,2TMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3665.6 | Semi standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,2TMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3377.0 | Standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,2TMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C)C3CCC4CC(O[Si](C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 4130.1 | Standard polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TBDMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3917.1 | Semi standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TBDMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3622.3 | Standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TBDMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 4296.4 | Standard polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TBDMS,isomer #2 | CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3892.8 | Semi standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TBDMS,isomer #2 | CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3657.5 | Standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,1TBDMS,isomer #2 | CC(=O)OC1CC2(O)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 4347.9 | Standard polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,2TBDMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 4103.2 | Semi standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,2TBDMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 3861.8 | Standard non polar | 33892256 | 16-(Acetyloxy)-3,14-dihydroxycard-20(22)-enolide,2TBDMS,isomer #1 | CC(=O)OC1CC2(O[Si](C)(C)C(C)(C)C)C3CCC4CC(O[Si](C)(C)C(C)(C)C)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC1 | 4319.0 | Standard polar | 33892256 |
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