Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-12 00:08:31 UTC |
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Update Date | 2022-03-07 02:55:55 UTC |
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HMDB ID | HMDB0038797 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Uralenolide |
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Description | Uralenolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, uralenolide has been detected, but not quantified in, herbs and spices. This could make uralenolide a potential biomarker for the consumption of these foods. |
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Structure | C[C@@]12C[C@@H](OC1=O)[C@]1(C)CC[C@]3(C)C(C=CC4[C@@]5(C)CC[C@H](O)[C@](C)(CO)C5CC[C@@]34C)=C1C2 InChI=1S/C30H44O4/c1-25-15-19-18-7-8-21-27(3)11-10-22(32)28(4,17-31)20(27)9-12-30(21,6)29(18,5)14-13-26(19,2)23(16-25)34-24(25)33/h7-8,20-23,31-32H,9-17H2,1-6H3/t20?,21?,22-,23+,25+,26+,27-,28+,29+,30+/m0/s1 |
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Synonyms | Value | Source |
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3b,24-Dihydroxy-11,13(18)-oleanadien-30,22b-olide | HMDB | Uralenolide | MeSH |
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Chemical Formula | C30H44O4 |
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Average Molecular Weight | 468.668 |
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Monoisotopic Molecular Weight | 468.323959896 |
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IUPAC Name | (1R,2R,5S,6R,10S,11S,14S,21R)-11-hydroxy-10-(hydroxymethyl)-2,5,6,10,14,21-hexamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracosa-16,18-dien-22-one |
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Traditional Name | (1R,2R,5S,6R,10S,11S,14S,21R)-11-hydroxy-10-(hydroxymethyl)-2,5,6,10,14,21-hexamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracosa-16,18-dien-22-one |
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CAS Registry Number | 111150-27-7 |
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SMILES | C[C@@]12C[C@@H](OC1=O)[C@]1(C)CC[C@]3(C)C(C=CC4[C@@]5(C)CC[C@H](O)[C@](C)(CO)C5CC[C@@]34C)=C1C2 |
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InChI Identifier | InChI=1S/C30H44O4/c1-25-15-19-18-7-8-21-27(3)11-10-22(32)28(4,17-31)20(27)9-12-30(21,6)29(18,5)14-13-26(19,2)23(16-25)34-24(25)33/h7-8,20-23,31-32H,9-17H2,1-6H3/t20?,21?,22-,23+,25+,26+,27-,28+,29+,30+/m0/s1 |
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InChI Key | RIARKSMMKCXBML-CTNZCSMESA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as steroids and steroid derivatives. These are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. |
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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 | Not Available |
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Direct Parent | Steroids and steroid derivatives |
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Alternative Parents | |
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Substituents | - Steroid
- Caprolactone
- Oxepane
- Gamma butyrolactone
- Cyclic alcohol
- Tetrahydrofuran
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Carbonyl group
- Primary alcohol
- Organic oxygen 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 | 302 - 303 °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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Uralenolide,1TMS,isomer #1 | C[C@]12CC[C@H](O[Si](C)(C)C)[C@](C)(CO)C1CC[C@]1(C)C2C=CC2=C3C[C@]4(C)C[C@@H](OC4=O)[C@]3(C)CC[C@]21C | 3822.9 | Semi standard non polar | 33892256 | Uralenolide,1TMS,isomer #2 | C[C@]12CC[C@H](O)[C@](C)(CO[Si](C)(C)C)C1CC[C@]1(C)C2C=CC2=C3C[C@]4(C)C[C@@H](OC4=O)[C@]3(C)CC[C@]21C | 3774.4 | Semi standard non polar | 33892256 | Uralenolide,2TMS,isomer #1 | C[C@]12CC[C@H](O[Si](C)(C)C)[C@](C)(CO[Si](C)(C)C)C1CC[C@]1(C)C2C=CC2=C3C[C@]4(C)C[C@@H](OC4=O)[C@]3(C)CC[C@]21C | 3768.6 | Semi standard non polar | 33892256 | Uralenolide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(CC[C@]3(C)C2C=CC2=C4C[C@]5(C)C[C@@H](OC5=O)[C@]4(C)CC[C@]23C)[C@@]1(C)CO | 4050.0 | Semi standard non polar | 33892256 | Uralenolide,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC[C@]1(C)C2CC[C@]3(C)C(C=CC4=C5C[C@]6(C)C[C@@H](OC6=O)[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O | 4026.7 | Semi standard non polar | 33892256 | Uralenolide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC[C@]1(C)C2CC[C@]3(C)C(C=CC4=C5C[C@]6(C)C[C@@H](OC6=O)[C@]5(C)CC[C@]43C)[C@@]2(C)CC[C@@H]1O[Si](C)(C)C(C)(C)C | 4222.9 | Semi standard non polar | 33892256 |
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