Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 13:23:49 UTC |
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Updated at | 2022-09-12 13:23:50 UTC |
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NP-MRD ID | NP0329210 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one |
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Description | 9Beta,20-dihydroxyecdysone belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. (1s,3as,5ar,7r,8s,9as,9br,11ar)-3a,7,8,9b-tetrahydroxy-9a,11a-dimethyl-1-[(2r,3s)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1h,2h,3h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one is found in Silene italica. It was first documented in 2004 (PMID: 15219788). Based on a literature review a significant number of articles have been published on 9beta,20-dihydroxyecdysone (PMID: 36130844) (PMID: 36130843) (PMID: 36130842) (PMID: 36130841). |
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Structure | CC(C)(O)CC[C@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@]3(O)CC[C@]12C InChI=1S/C27H44O8/c1-22(2,32)8-7-21(31)25(5,33)19-6-9-26(34)20-13-16(28)15-12-17(29)18(30)14-24(15,4)27(20,35)11-10-23(19,26)3/h13,15,17-19,21,29-35H,6-12,14H2,1-5H3/t15-,17+,18-,19-,21-,23+,24-,25+,26+,27-/m0/s1 |
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Synonyms | Value | Source |
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9b,20-Dihydroxyecdysone | Generator | 9Β,20-dihydroxyecdysone | Generator |
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Chemical Formula | C27H44O8 |
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Average Mass | 496.6410 Da |
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Monoisotopic Mass | 496.30362 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | CC(C)(O)CC[C@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@]3(O)CC[C@]12C |
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InChI Identifier | InChI=1S/C27H44O8/c1-22(2,32)8-7-21(31)25(5,33)19-6-9-26(34)20-13-16(28)15-12-17(29)18(30)14-24(15,4)27(20,35)11-10-23(19,26)3/h13,15,17-19,21,29-35H,6-12,14H2,1-5H3/t15-,17+,18-,19-,21-,23+,24-,25+,26+,27-/m0/s1 |
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InChI Key | AHHRNGCAWAPZKG-KEBLQTTMSA-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 hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. |
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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 | Bile acids, alcohols and derivatives |
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Direct Parent | Hydroxy bile acids, alcohols and derivatives |
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Alternative Parents | |
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Substituents | - Hexahydroxy bile acid, alcohol, or derivatives
- Cholesterol
- Cholesterol-skeleton
- Cholestane-skeleton
- Ecdysteroid
- 25-hydroxysteroid
- Hydroxy bile acid, alcohol, or derivatives
- 22-hydroxysteroid
- 20-hydroxysteroid
- 3-hydroxy-delta-7-steroid
- 2-hydroxysteroid
- 3-beta-hydroxysteroid
- Oxosteroid
- 6-oxosteroid
- Hydroxysteroid
- 3-hydroxysteroid
- 14-hydroxysteroid
- Delta-7-steroid
- Cyclohexenone
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Polyol
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Alcohol
- 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 ]
- Simon A, Pongracz Z, Toth G, Mak M, Mathe I, Bathori M: A new ecdysteroid with unique 9beta-OH and four other ecdysteroids from Silene italica ssp. nemoralis. Steroids. 2004 Jun;69(6):389-94. doi: 10.1016/j.steroids.2004.03.009. [PubMed:15219788 ]
- LOTUS database [Link]
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