Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 19:09:13 UTC |
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Update Date | 2022-03-07 02:54:04 UTC |
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HMDB ID | HMDB0034339 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ixocarpalactone B |
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Description | Ixocarpalactone B belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Ixocarpalactone B is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC1C(C)C2(OC1=O)OC1CC3C4CC5OC55C(O)C=CC(=O)C5(C)C4CCC3(C)C1C(C)(O)C2O InChI=1S/C28H38O8/c1-12-13(2)28(36-22(12)31)23(32)26(5,33)21-17(34-28)11-16-14-10-20-27(35-20)19(30)7-6-18(29)25(27,4)15(14)8-9-24(16,21)3/h6-7,12-17,19-21,23,30,32-33H,8-11H2,1-5H3 |
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Synonyms | Value | Source |
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5,6B;16b,23S-diepoxy-4b,20R,22S-trihydroxy-1-oxo-5b-ergost-2-eno-26,23S-lactone | HMDB |
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Chemical Formula | C28H38O8 |
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Average Molecular Weight | 502.5965 |
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Monoisotopic Molecular Weight | 502.256668192 |
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IUPAC Name | 7,8,18-trihydroxy-3',4',8,10,14-pentamethyl-5,20-dioxaspiro[hexacyclo[11.9.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹.0¹⁹,²¹]docosane-6,2'-oxolan]-16-ene-5',15-dione |
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Traditional Name | 7,8,18-trihydroxy-3',4',8,10,14-pentamethyl-5,20-dioxaspiro[hexacyclo[11.9.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹.0¹⁹,²¹]docosane-6,2'-oxolan]-16-ene-5',15-dione |
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CAS Registry Number | 71801-44-0 |
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SMILES | CC1C(C)C2(OC1=O)OC1CC3C4CC5OC55C(O)C=CC(=O)C5(C)C4CCC3(C)C1C(C)(O)C2O |
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InChI Identifier | InChI=1S/C28H38O8/c1-12-13(2)28(36-22(12)31)23(32)26(5,33)21-17(34-28)11-16-14-10-20-27(35-20)19(30)7-6-18(29)25(27,4)15(14)8-9-24(16,21)3/h6-7,12-17,19-21,23,30,32-33H,8-11H2,1-5H3 |
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InChI Key | RJARWAVNDSGUGC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. |
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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 | Withanolides and derivatives |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Spirostane skeleton
- Withanolide-skeleton
- Prostaglandin skeleton
- Eicosanoid
- 5,6-epoxysteroid
- Oxepane
- Ketal
- Cyclohexenone
- Fatty acyl
- Gamma butyrolactone
- Monosaccharide
- Oxane
- Tetrahydrofuran
- Tertiary alcohol
- Carboxylic acid ester
- Secondary alcohol
- Ketone
- Lactone
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Dialkyl ether
- Oxirane
- Ether
- Polyol
- Acetal
- Monocarboxylic acid or derivatives
- Organic oxide
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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 | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 145 - 148 °C | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Ixocarpalactone B,1TMS,isomer #1 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O[Si](C)(C)C)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O)C2O)C1C | 4113.1 | Semi standard non polar | 33892256 | Ixocarpalactone B,1TMS,isomer #2 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O[Si](C)(C)C)C2O)C1C | 4095.4 | Semi standard non polar | 33892256 | Ixocarpalactone B,1TMS,isomer #3 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O)C2O[Si](C)(C)C)C1C | 4093.7 | Semi standard non polar | 33892256 | Ixocarpalactone B,2TMS,isomer #1 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O[Si](C)(C)C)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O[Si](C)(C)C)C2O)C1C | 4013.1 | Semi standard non polar | 33892256 | Ixocarpalactone B,2TMS,isomer #2 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O[Si](C)(C)C)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O)C2O[Si](C)(C)C)C1C | 4013.7 | Semi standard non polar | 33892256 | Ixocarpalactone B,2TMS,isomer #3 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O[Si](C)(C)C)C2O[Si](C)(C)C)C1C | 4009.0 | Semi standard non polar | 33892256 | Ixocarpalactone B,3TMS,isomer #1 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O[Si](C)(C)C)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O[Si](C)(C)C)C2O[Si](C)(C)C)C1C | 3916.5 | Semi standard non polar | 33892256 | Ixocarpalactone B,1TBDMS,isomer #1 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O[Si](C)(C)C(C)(C)C)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O)C2O)C1C | 4346.5 | Semi standard non polar | 33892256 | Ixocarpalactone B,1TBDMS,isomer #2 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O[Si](C)(C)C(C)(C)C)C2O)C1C | 4329.8 | Semi standard non polar | 33892256 | Ixocarpalactone B,1TBDMS,isomer #3 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O)C2O[Si](C)(C)C(C)(C)C)C1C | 4320.8 | Semi standard non polar | 33892256 | Ixocarpalactone B,2TBDMS,isomer #1 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O[Si](C)(C)C(C)(C)C)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O[Si](C)(C)C(C)(C)C)C2O)C1C | 4463.9 | Semi standard non polar | 33892256 | Ixocarpalactone B,2TBDMS,isomer #2 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O[Si](C)(C)C(C)(C)C)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O)C2O[Si](C)(C)C(C)(C)C)C1C | 4467.4 | Semi standard non polar | 33892256 | Ixocarpalactone B,2TBDMS,isomer #3 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C1C | 4454.5 | Semi standard non polar | 33892256 | Ixocarpalactone B,3TBDMS,isomer #1 | CC1C(=O)OC2(OC3CC4C5CC6OC67C(O[Si](C)(C)C(C)(C)C)C=CC(=O)C7(C)C5CCC4(C)C3C(C)(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C1C | 4560.5 | Semi standard non polar | 33892256 |
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