Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 05:34:54 UTC |
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Updated at | 2022-09-12 05:34:54 UTC |
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NP-MRD ID | NP0325092 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol |
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Description | Stigmastadienol 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. (6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylhepta-1,3-dien-1-ol is found in Hippophae rhamnoides. It was first documented in 2008 (PMID: 26049228). Based on a literature review a significant number of articles have been published on Stigmastadienol (PMID: 36130844) (PMID: 36130843) (PMID: 36130842) (PMID: 36130841) (PMID: 36130840) (PMID: 36130836). |
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Structure | C[C@H](CC=C(C=CO)C(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C InChI=1S/C29H48O/c1-20(2)22(16-19-30)10-9-21(3)25-13-14-26-24-12-11-23-8-6-7-17-28(23,4)27(24)15-18-29(25,26)5/h10,16,19-21,23-27,30H,6-9,11-15,17-18H2,1-5H3/t21-,23?,24+,25-,26+,27+,28+,29-/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C29H48O |
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Average Mass | 412.7020 Da |
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Monoisotopic Mass | 412.37052 Da |
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IUPAC Name | (6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-(propan-2-yl)hepta-1,3-dien-1-ol |
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Traditional Name | (6R)-6-[(1S,2S,10R,11S,14R,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-3-isopropylhepta-1,3-dien-1-ol |
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CAS Registry Number | Not Available |
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SMILES | C[C@H](CC=C(C=CO)C(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4CCCC[C@]4(C)[C@H]3CC[C@]12C |
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InChI Identifier | InChI=1S/C29H48O/c1-20(2)22(16-19-30)10-9-21(3)25-13-14-26-24-12-11-23-8-6-7-17-28(23,4)27(24)15-18-29(25,26)5/h10,16,19-21,23-27,30H,6-9,11-15,17-18H2,1-5H3/t21-,23?,24+,25-,26+,27+,28+,29-/m1/s1 |
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InChI Key | DSOKBBPJHVYCBQ-KZSQEHGRSA-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
- Enol
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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 | - Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
- Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
- Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
- Khamis S, Mitakidou MR, Champion M, Goyal S, Jones RL, Siddiqui A, Sabanathan S, Hedderly T, Lin JP, Jungbluth H, Papandreou A: Clinical Reasoning: A Teenage Girl With Progressive Hyperkinetic Movements, Seizures, and Encephalopathy. Neurology. 2022 Sep 21. pii: WNL.0000000000201385. doi: 10.1212/WNL.0000000000201385. [PubMed:36130841 ]
- Rosenberg A, Ohlund-Wistbacka U, Hall A, Bonnard A, Hagman G, Ryden M, Thunborg C, Wiggenraad F, Sandebring-Matton A, Solomon A, Kivipelto M: beta-Amyloid, Tau, Neurodegeneration Classification and Eligibility for Anti-amyloid Treatment in a Memory Clinic Population. Neurology. 2022 Sep 21. pii: WNL.0000000000201043. doi: 10.1212/WNL.0000000000201043. [PubMed:36130840 ]
- Yu H, Cai G, Wu J, Li Q: Clinical Phenotypic Variability and Significance of Pneumolabyrinth After Tympanum-Penetrating Injury. Ear Nose Throat J. 2022 Sep 21:1455613221128132. doi: 10.1177/01455613221128132. [PubMed:36130836 ]
- Bedford J, Martin P, Crowe S, Wagstaff D, Santos C, Singleton G, Baumber R, Vindrola-Padros C, Vohra R, Swart M, Oliver CM, Dorey J, Leeman I, Moonesinghe SR: Development and internal validation of a model for postoperative morbidity in adults undergoing major elective colorectal surgery: the peri-operative quality improvement programme (PQIP) colorectal risk model. Anaesthesia. 2022 Sep 21. doi: 10.1111/anae.15858. [PubMed:36130834 ]
- Silverman A, Beres S: Child Neurology: Horner Syndrome in an Otherwise Well-Appearing Infant. Neurology. 2022 Sep 21. pii: WNL.0000000000201377. doi: 10.1212/WNL.0000000000201377. [PubMed:36130839 ]
- Harada Y, Wang SH, Juel VC: Clinical Reasoning: A 36-Year-Old Man With Asymmetric Muscle Weakness. Neurology. 2022 Sep 21. pii: WNL.0000000000201379. doi: 10.1212/WNL.0000000000201379. [PubMed:36130838 ]
- Guest O, Memon AA, Chukweubuka A, Zaheer M, Siddiqi N: Robotic low anterior resection for locally advanced rectal cancer - A video vignette. Colorectal Dis. 2022 Sep 21. doi: 10.1111/codi.16345. [PubMed:36130837 ]
- Pellicori P, Kalra PR, Clark AL, Friday JM, Cleland JGF: Chronic kidney disease (CKD) and CKD-ism in heart failure - what a mess! Eur J Heart Fail. 2022 Sep 21. doi: 10.1002/ejhf.2696. [PubMed:36130835 ]
- Ammar S, Kelebek H, Zribi A, Abichou M, Selli S, Bouaziz M: LC-DAD/ESI-MS/MS characterization of phenolic constituents in Tunisian extra-virgin olive oils: Effect of olive leaves addition on chemical composition. Food Res Int. 2017 Oct;100(Pt 3):477-485. doi: 10.1016/j.foodres.2016.11.001. Epub 2016 Nov 5. [PubMed:28964371 ]
- Balbino S, Vincek D, Trtanj I, Egredija D, Gajdos-Kljusuric J, Kraljic K, Obranovic M, Skevin D: Assessment of Pumpkin Seed Oil Adulteration Supported by Multivariate Analysis: Comparison of GC-MS, Colourimetry and NIR Spectroscopy Data. Foods. 2022 Mar 14;11(6):835. doi: 10.3390/foods11060835. [PubMed:35327258 ]
- Duman E, Ozcan MM: The influence of industrial refining stages on the physico-chemical properties, fatty acid composition and sterol contents in hazelnut oil. J Food Sci Technol. 2020 Jul;57(7):2501-2506. doi: 10.1007/s13197-020-04285-w. Epub 2020 Feb 3. [PubMed:32549600 ]
- Gornas P, Czubinski J, Rudzinska M, Grygier A, Ying Q, Chakradhari S, Sahu PK, Misina I, Urvaka E, Patel KS: Selected Uncommon Legumes as a Source of Essential Fatty Acids, Tocopherols, Tocotrienols, Sterols, Carotenoids, and Squalene. Plant Foods Hum Nutr. 2019 Mar;74(1):91-98. doi: 10.1007/s11130-018-0706-x. [PubMed:30552561 ]
- Montesano D, Blasi F, Simonetti MS, Santini A, Cossignani L: Chemical and Nutritional Characterization of Seed Oil from Cucurbita maxima L. (var. Berrettina) Pumpkin. Foods. 2018 Mar 1;7(3):30. doi: 10.3390/foods7030030. [PubMed:29494522 ]
- Yuan X, Su Q, Wang H, Shi S, Liu L, Lv J, Wang S, Zhu L, Zhang H: Genetic Variants of the COL4A3 , COL4A4 , and COL4A5 Genes Contribute to Thinned Glomerular Basement Membrane Lesions in Sporadic IgA Nephropathy Patients. J Am Soc Nephrol. 2023 Jan 1;34(1):132-144. doi: 10.1681/ASN.2021111447. Epub 2022 Oct 5. [PubMed:36130833 ]
- Wu C, O'Keeffe C, Sanford J, Hagel J, Childs S, Evers G, Melbourne J, West C, Koch M, Cornia PB: Simple signature/countersignature shared-accountability quality improvement initiative to improve reliability of blood sample collection: an essential clinical task. BMJ Open Qual. 2022 Sep;11(3):e001765. doi: 10.1136/bmjoq-2021-001765. [PubMed:36130832 ]
- Soltana H, Tekaya M, Amri Z, El-Gharbi S, Nakbi A, Harzallah A, Mechri B, Hammami M: Characterization of fig achenes' oil of Ficus carica grown in Tunisia. Food Chem. 2016 Apr 1;196:1125-30. doi: 10.1016/j.foodchem.2015.10.053. Epub 2015 Oct 22. [PubMed:26593597 ]
- Kim JA, Son JH, Song SB, Yang SY, Kim YH: Sterols isolated from seeds of Panax ginseng and their antiinflammatory activities. Pharmacogn Mag. 2013 Apr;9(34):182-5. doi: 10.4103/0973-1296.111288. [PubMed:23772116 ]
- Lukic M, Lukic I, Krapac M, Sladonja B, Pilizota V: Sterols and triterpene diols in olive oil as indicators of variety and degree of ripening. Food Chem. 2013 Jan 1;136(1):251-8. doi: 10.1016/j.foodchem.2012.08.005. Epub 2012 Aug 11. [PubMed:23017420 ]
- Shin EC, Pegg RB, Phillips RD, Eitenmiller RR: Commercial peanut (Arachis hypogaea L.) cultivars in the United States: phytosterol composition. J Agric Food Chem. 2010 Aug 25;58(16):9137-46. doi: 10.1021/jf102150n. Epub 2010 Aug 2. [PubMed:20677801 ]
- Temime SB, Manai H, Methenni K, Baccouri B, Abaza L, Daoud D, Casas JS, Bueno EO, Zarrouk M: Sterolic composition of Chetoui virgin olive oil: Influence of geographical origin. Food Chem. 2008 Sep 15;110(2):368-74. doi: 10.1016/j.foodchem.2008.02.012. Epub 2008 Feb 14. [PubMed:26049228 ]
- LOTUS database [Link]
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