Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-11 17:51:11 UTC |
---|
Update Date | 2022-03-07 02:53:26 UTC |
---|
HMDB ID | HMDB0032685 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide |
---|
Description | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 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 (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide is an extremely weak basic (essentially neutral) compound (based on its pKa). |
---|
Structure | CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C InChI=1S/C28H36O5/c1-16-15-22(32-23(30)17(16)2)26(5)28(31)14-13-27(33-26)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6-7,9,19-20,22,31H,8,10-15H2,1-5H3 |
---|
Synonyms | Value | Source |
---|
(14a,17b,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide | Generator | (14Α,17β,20S,22R)-14,20-epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide | Generator |
|
---|
Chemical Formula | C28H36O5 |
---|
Average Molecular Weight | 452.5824 |
---|
Monoisotopic Molecular Weight | 452.256274262 |
---|
IUPAC Name | 16-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one |
---|
Traditional Name | 16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one |
---|
CAS Registry Number | Not Available |
---|
SMILES | CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C |
---|
InChI Identifier | InChI=1S/C28H36O5/c1-16-15-22(32-23(30)17(16)2)26(5)28(31)14-13-27(33-26)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6-7,9,19-20,22,31H,8,10-15H2,1-5H3 |
---|
InChI Key | KOYNICXFSFFIPU-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Steroid lactones |
---|
Direct Parent | Withanolides and derivatives |
---|
Alternative Parents | Not Available |
---|
Substituents | Not Available |
---|
Molecular Framework | Aliphatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | 192 - 193 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
---|
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide | CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C | 4585.5 | Standard polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide | CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C | 3322.5 | Standard non polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide | CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C | 4002.1 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,1TMS,isomer #1 | CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C)C3(C)CCC2C4CC=C3C=CCC(=O)C32C)C1 | 3803.2 | Semi standard non polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,1TMS,isomer #2 | CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C)C32C)C1 | 3750.3 | Semi standard non polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,2TMS,isomer #1 | CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C)C32C)C1 | 3789.2 | Semi standard non polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,2TMS,isomer #1 | CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C)C32C)C1 | 3623.2 | Standard non polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,1TBDMS,isomer #1 | CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CCC2C4CC=C3C=CCC(=O)C32C)C1 | 4037.7 | Semi standard non polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,1TBDMS,isomer #2 | CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C(C)(C)C)C32C)C1 | 3976.0 | Semi standard non polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,2TBDMS,isomer #1 | CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C(C)(C)C)C32C)C1 | 4238.1 | Semi standard non polar | 33892256 | (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,2TBDMS,isomer #1 | CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C(C)(C)C)C32C)C1 | 4076.7 | Standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide GC-MS (Non-derivatized) - 70eV, Positive | splash10-003i-5893600000-e53d4ccf4fcc74d2a9ac | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide GC-MS (1 TMS) - 70eV, Positive | splash10-0a4i-5509350000-b3e360222f23f8242978 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 10V, Positive-QTOF | splash10-0udi-0102900000-ed52c032774b8d3cc85d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 20V, Positive-QTOF | splash10-0udi-9107400000-84e673e3ace95618e03b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 40V, Positive-QTOF | splash10-0uyr-9474200000-fbfc8ef57fcafd44cb0c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 10V, Negative-QTOF | splash10-0udi-0002900000-a1a519533d32bcf115c6 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 20V, Negative-QTOF | splash10-0zfr-1003900000-1a7c20ce888212ac3d57 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 40V, Negative-QTOF | splash10-02t9-9203000000-aff88b35db039e3664ca | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 10V, Positive-QTOF | splash10-0udi-0000900000-159b2996bf6fe76614e4 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 20V, Positive-QTOF | splash10-0udr-4338900000-d38aebf7f02d6fec872b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 40V, Positive-QTOF | splash10-0j4r-4928100000-1bb4260ea21842302f3e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 10V, Negative-QTOF | splash10-0udi-0000900000-169e1b4194a44a788bba | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 20V, Negative-QTOF | splash10-0fb9-2109700000-4eae2bb02656d7cd3a69 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 40V, Negative-QTOF | splash10-0fn9-9300100000-a8985d2a0afcf49ad95b | 2021-09-24 | Wishart Lab | View Spectrum |
|
---|