Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 15:42:50 UTC |
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Updated at | 2022-09-12 15:42:50 UTC |
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NP-MRD ID | NP0330397 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1r,3ar,9as,9br,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol |
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Description | Delta(7)-Stigmastenol, also known as 22,23-dihydrospinasterol or schottenol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. (1r,3ar,9as,9br,11ar)-1-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Trigonella foenum-graecum. It was first documented in 2017 (PMID: 28381771). Based on a literature review a significant number of articles have been published on delta(7)-Stigmastenol (PMID: 35248579) (PMID: 29946260) (PMID: 28301152) (PMID: 28078712). |
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Structure | CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4CC(O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h11,19-23,25-27,30H,7-10,12-18H2,1-6H3/t20-,21-,22?,23?,25-,26+,27+,28+,29-/m1/s1 |
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Synonyms | Value | Source |
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Δ(7)-stigmastenol | Generator | 22,23-Dihydrospinasterol | MeSH | Schottenol | MeSH | Stigmast-7-enol, (3beta,5alpha)-isomer | MeSH | Stigmast-7-enol, (3beta,5alpha,24S)-isomer | MeSH | Stigmast-7-enol | MeSH | Stigmast-7-en-3-ol | MeSH |
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Chemical Formula | C29H50O |
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Average Mass | 414.7180 Da |
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Monoisotopic Mass | 414.38617 Da |
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IUPAC Name | (1R,2S,11R,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol |
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Traditional Name | (1R,2S,11R,14R,15R)-14-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol |
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CAS Registry Number | Not Available |
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SMILES | CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2C3=CCC4CC(O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C |
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InChI Identifier | InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h11,19-23,25-27,30H,7-10,12-18H2,1-6H3/t20-,21-,22?,23?,25-,26+,27+,28+,29-/m1/s1 |
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InChI Key | YSKVBPGQYRAUQO-MNMXQYNKSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. |
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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 | Stigmastanes and derivatives |
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Direct Parent | Stigmastanes and derivatives |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Stigmastane-skeleton
- Hydroxysteroid
- 3-hydroxysteroid
- 3-hydroxy-delta-7-steroid
- Delta-7-steroid
- Cyclic alcohol
- Secondary alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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General References | - Rozentsvet OA, Kotlova ER, Bogdanova ES, Nesterov VN, Senik SV, Shavarda AL: Balance of Delta(5)-and Delta(7)-sterols and stanols in halophytes in connection with salinity tolerance. Phytochemistry. 2022 Jun;198:113156. doi: 10.1016/j.phytochem.2022.113156. Epub 2022 Mar 4. [PubMed:35248579 ]
- Yang Y, Zhang P, Wang Y, Wei S, Zhang L, Wang J, Lu X, Zhou H, Li R, Wen J, Zhou X, Li H, Li K, Zhao Y: Hepatoprotective Effect of San-Cao Granule on Con A-Induced Liver Injury in Mice and Mechanisms of Action Exploration. Front Pharmacol. 2018 Jun 12;9:624. doi: 10.3389/fphar.2018.00624. eCollection 2018. [PubMed:29946260 ]
- Lodolini EM, Polverigiani S, Ali S, Mutawea M, Qutub M, Arabasi T, Pierini F, Abed M, Neri D: Oil Characteristics of Four Palestinian Olive Varieties. J Oleo Sci. 2017 May 1;66(5):435-441. doi: 10.5650/jos.ess16184. Epub 2017 Apr 4. [PubMed:28381771 ]
- Chtourou F, Jabeur H, Lazzez A, Bouaziz M: Characterization and Discrimination of Oueslati Virgin Olive Oils from Adult and Young Trees in Different Ripening Stages Using Sterols, Pigments, and Alcohols in Tandem with Chemometrics. J Agric Food Chem. 2017 May 3;65(17):3512-3522. doi: 10.1021/acs.jafc.6b04122. Epub 2017 Apr 21. [PubMed:28301152 ]
- Ozkan A, Aboul-Enein HY, Kulak M, Bindak R: Comparative study on fatty acid composition of olive (Olea europaea L.), with emphasis on phytosterol contents. Biomed Chromatogr. 2017 Aug;31(8). doi: 10.1002/bmc.3933. Epub 2017 Feb 6. [PubMed:28078712 ]
- LOTUS database [Link]
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