Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-12 00:26:22 UTC |
---|
Update Date | 2022-03-07 02:56:04 UTC |
---|
HMDB ID | HMDB0039081 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Physalin O |
---|
Description | Physalin O belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). Physalin O is an extremely weak basic (essentially neutral) compound (based on its pKa). |
---|
Structure | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC11C2(C)OC(=O)C1(O)CCC1C3C(O)C=C2CC=CC(=O)C12C InChI=1S/C28H32O10/c1-12-21(32)36-17-11-23(12,2)19-20(31)27(35)18-14(24(3)13(10-15(18)29)6-5-7-16(24)30)8-9-26(34)22(33)37-25(17,4)28(19,26)38-27/h5,7,10,12,14-15,17-19,29,34-35H,6,8-9,11H2,1-4H3 |
---|
Synonyms | Value | Source |
---|
(25S)-25,27-Dihydrophysalin a | HMDB | Physalin O | MeSH |
|
---|
Chemical Formula | C28H32O10 |
---|
Average Molecular Weight | 528.5477 |
---|
Monoisotopic Molecular Weight | 528.199547244 |
---|
IUPAC Name | 5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,11-diene-13,19,24,27-tetrone |
---|
Traditional Name | 5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,11-diene-13,19,24,27-tetrone |
---|
CAS Registry Number | 120849-18-5 |
---|
SMILES | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC11C2(C)OC(=O)C1(O)CCC1C3C(O)C=C2CC=CC(=O)C12C |
---|
InChI Identifier | InChI=1S/C28H32O10/c1-12-21(32)36-17-11-23(12,2)19-20(31)27(35)18-14(24(3)13(10-15(18)29)6-5-7-16(24)30)8-9-26(34)22(33)37-25(17,4)28(19,26)38-27/h5,7,10,12,14-15,17-19,29,34-35H,6,8-9,11H2,1-4H3 |
---|
InChI Key | QFAOFAWTSOFSQA-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Steroids and steroid derivatives |
---|
Sub Class | Physalins and derivatives |
---|
Direct Parent | Physalins and derivatives |
---|
Alternative Parents | |
---|
Substituents | - Physalin skeleton
- Delta valerolactone
- Cyclohexenone
- Delta_valerolactone
- Dicarboxylic acid or derivatives
- 3-furanone
- Gamma butyrolactone
- Oxane
- Cyclic alcohol
- Tetrahydrofuran
- Tertiary alcohol
- Lactone
- Ketone
- Hemiacetal
- Carboxylic acid ester
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Polyol
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Alcohol
- Carbonyl group
- Aliphatic heteropolycyclic compound
|
---|
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 | 272 - 273 °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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Physalin O,1TMS,isomer #1 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O[Si](C)(C)C)OC14C(O)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4255.2 | Semi standard non polar | 33892256 | Physalin O,1TMS,isomer #2 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC14C(O[Si](C)(C)C)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4271.7 | Semi standard non polar | 33892256 | Physalin O,1TMS,isomer #3 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC14C(O)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4230.2 | Semi standard non polar | 33892256 | Physalin O,1TMS,isomer #4 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O)OC14C(O)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4072.7 | Semi standard non polar | 33892256 | Physalin O,2TMS,isomer #1 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O[Si](C)(C)C)OC14C(O[Si](C)(C)C)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4252.2 | Semi standard non polar | 33892256 | Physalin O,2TMS,isomer #2 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O[Si](C)(C)C)OC14C(O)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4192.3 | Semi standard non polar | 33892256 | Physalin O,2TMS,isomer #3 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O[Si](C)(C)C)OC14C(O)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4054.2 | Semi standard non polar | 33892256 | Physalin O,2TMS,isomer #4 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC14C(O[Si](C)(C)C)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4215.0 | Semi standard non polar | 33892256 | Physalin O,2TMS,isomer #5 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O)OC14C(O[Si](C)(C)C)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4067.2 | Semi standard non polar | 33892256 | Physalin O,2TMS,isomer #6 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O)OC14C(O)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4004.0 | Semi standard non polar | 33892256 | Physalin O,3TMS,isomer #1 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O[Si](C)(C)C)OC14C(O[Si](C)(C)C)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4171.1 | Semi standard non polar | 33892256 | Physalin O,3TMS,isomer #2 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O[Si](C)(C)C)OC14C(O[Si](C)(C)C)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4031.9 | Semi standard non polar | 33892256 | Physalin O,3TMS,isomer #3 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O[Si](C)(C)C)OC14C(O)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 3980.3 | Semi standard non polar | 33892256 | Physalin O,3TMS,isomer #4 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O)OC14C(O[Si](C)(C)C)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 3994.0 | Semi standard non polar | 33892256 | Physalin O,4TMS,isomer #1 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O[Si](C)(C)C)OC14C(O[Si](C)(C)C)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 3944.9 | Semi standard non polar | 33892256 | Physalin O,4TMS,isomer #1 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C)C3(O[Si](C)(C)C)OC14C(O[Si](C)(C)C)(CCC1C3C(O[Si](C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 3989.0 | Standard non polar | 33892256 | Physalin O,1TBDMS,isomer #1 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O[Si](C)(C)C(C)(C)C)OC14C(O)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4498.5 | Semi standard non polar | 33892256 | Physalin O,1TBDMS,isomer #2 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4517.6 | Semi standard non polar | 33892256 | Physalin O,1TBDMS,isomer #3 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC14C(O)(CCC1C3C(O[Si](C)(C)C(C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4465.1 | Semi standard non polar | 33892256 | Physalin O,1TBDMS,isomer #4 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C(C)(C)C)C3(O)OC14C(O)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4306.0 | Semi standard non polar | 33892256 | Physalin O,2TBDMS,isomer #1 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O[Si](C)(C)C(C)(C)C)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4742.0 | Semi standard non polar | 33892256 | Physalin O,2TBDMS,isomer #2 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O[Si](C)(C)C(C)(C)C)OC14C(O)(CCC1C3C(O[Si](C)(C)C(C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4668.4 | Semi standard non polar | 33892256 | Physalin O,2TBDMS,isomer #3 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C(C)(C)C)C3(O[Si](C)(C)C(C)(C)C)OC14C(O)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4511.0 | Semi standard non polar | 33892256 | Physalin O,2TBDMS,isomer #4 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C(O[Si](C)(C)C(C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4710.0 | Semi standard non polar | 33892256 | Physalin O,2TBDMS,isomer #5 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C(C)(C)C)C3(O)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4527.7 | Semi standard non polar | 33892256 | Physalin O,2TBDMS,isomer #6 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C(C)(C)C)C3(O)OC14C(O)(CCC1C3C(O[Si](C)(C)C(C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4466.5 | Semi standard non polar | 33892256 | Physalin O,3TBDMS,isomer #1 | CC1C(=O)OC2CC1(C)C1C(=O)C3(O[Si](C)(C)C(C)(C)C)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C(O[Si](C)(C)C(C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4883.9 | Semi standard non polar | 33892256 | Physalin O,3TBDMS,isomer #2 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C(C)(C)C)C3(O[Si](C)(C)C(C)(C)C)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C(O)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4699.6 | Semi standard non polar | 33892256 | Physalin O,3TBDMS,isomer #3 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C(C)(C)C)C3(O[Si](C)(C)C(C)(C)C)OC14C(O)(CCC1C3C(O[Si](C)(C)C(C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4647.5 | Semi standard non polar | 33892256 | Physalin O,3TBDMS,isomer #4 | CC1C(=O)OC2CC1(C)C1=C(O[Si](C)(C)C(C)(C)C)C3(O)OC14C(O[Si](C)(C)C(C)(C)C)(CCC1C3C(O[Si](C)(C)C(C)(C)C)C=C3CC=CC(=O)C31C)C(=O)OC24C | 4678.5 | Semi standard non polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f8a-0941430000-820092d5f5b542117f56 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (2 TMS) - 70eV, Positive | splash10-0pdj-2920017000-6686df33dbe8c414f490 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_3_2) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_3_3) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TMS_3_4) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_1_4) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_2_5) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Physalin O GC-MS (TBDMS_2_6) - 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 - Physalin O 10V, Positive-QTOF | splash10-03fr-0000490000-57b562bac73a61c7f135 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 20V, Positive-QTOF | splash10-03dl-0000950000-e41bf311cba018df55f3 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 40V, Positive-QTOF | splash10-0a4l-0001900000-86914e603692961aceb1 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 10V, Negative-QTOF | splash10-004i-0000590000-5f163f233961942f609c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 20V, Negative-QTOF | splash10-057i-0000690000-16c9c2ffc0fd8df8fab3 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 40V, Negative-QTOF | splash10-0f79-1960410000-b634d12109bde0486a73 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 10V, Positive-QTOF | splash10-004i-0000090000-9b53b52dcfbbd397362e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 20V, Positive-QTOF | splash10-004i-0100890000-bc6c8ef249b669505d69 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 40V, Positive-QTOF | splash10-0fk9-0900010000-2540e1502cf51fde8f7d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 10V, Negative-QTOF | splash10-004i-0000190000-dc66cc185ead90926e8f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 20V, Negative-QTOF | splash10-004i-0000190000-d193e36b8da7150fb2be | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Physalin O 40V, Negative-QTOF | splash10-056r-0540790000-625fbf24127438477897 | 2021-09-24 | Wishart Lab | View Spectrum |
|
---|