Record Information |
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Version | 1.0 |
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Created at | 2022-09-07 06:25:13 UTC |
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Updated at | 2022-09-07 06:25:13 UTC |
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NP-MRD ID | NP0245361 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (1s,3r,6s,8r,9s,11s,12s,14s,15r,16r)-15-[(2s,5r)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecane-6,9,14-triol |
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Description | Cycloastragenol, also known as cyclogalegigenin or astramembrangenin, belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. It was first documented in 2022 (PMID: 36029292). Based on a literature review a significant number of articles have been published on Cycloastragenol (PMID: 35904311) (PMID: 35203568) (PMID: 35718303) (PMID: 35693703). |
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Structure | CC(C)(O)[C@H]1CC[C@](C)(O1)[C@H]1[C@@H](O)C[C@@]2(C)[C@@H]3C[C@H](O)[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C InChI=1S/C30H50O5/c1-24(2)20(33)8-11-30-16-29(30)13-12-26(5)23(28(7)10-9-21(35-28)25(3,4)34)18(32)15-27(26,6)19(29)14-17(31)22(24)30/h17-23,31-34H,8-16H2,1-7H3/t17-,18-,19-,20-,21+,22-,23-,26+,27-,28-,29-,30+/m0/s1 |
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Synonyms | Value | Source |
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Cyclogalegigenin | MeSH | Astramembrangenin | MeSH |
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Chemical Formula | C30H50O5 |
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Average Mass | 490.7250 Da |
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Monoisotopic Mass | 490.36582 Da |
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IUPAC Name | (1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9,14-triol |
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Traditional Name | (1S,3R,6S,8R,9S,11S,12S,14S,15R,16R)-15-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecane-6,9,14-triol |
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CAS Registry Number | Not Available |
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SMILES | CC(C)(O)[C@H]1CC[C@](C)(O1)[C@H]1[C@@H](O)C[C@@]2(C)[C@@H]3C[C@H](O)[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C |
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InChI Identifier | InChI=1S/C30H50O5/c1-24(2)20(33)8-11-30-16-29(30)13-12-26(5)23(28(7)10-9-21(35-28)25(3,4)34)18(32)15-27(26,6)19(29)14-17(31)22(24)30/h17-23,31-34H,8-16H2,1-7H3/t17-,18-,19-,20-,21+,22-,23-,26+,27-,28-,29-,30+/m0/s1 |
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InChI Key | WENNXORDXYGDTP-ODAITAILSA-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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Terpene glycosides |
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Direct Parent | Triterpene saponins |
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Alternative Parents | |
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Substituents | - Triterpene saponin
- Cycloartanol-skeleton
- 9b,19-cyclo-lanostane-skeleton
- Cycloartane-skeleton
- Triterpenoid
- 3-hydroxysteroid
- 6-hydroxysteroid
- Hydroxysteroid
- 3-beta-hydroxysteroid
- 16-beta-hydroxysteroid
- 16-hydroxysteroid
- Steroid
- Tertiary alcohol
- Tetrahydrofuran
- Cyclic alcohol
- Secondary alcohol
- Polyol
- Ether
- Dialkyl ether
- Oxacycle
- Organoheterocyclic compound
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Hydrocarbon derivative
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic 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 | - Takeuchi DM, Kishino S, Ozeki Y, Fukami H, Ogawa J: Analysis of astragaloside IV metabolism to cycloastragenol in human gut microorganism, bifidobacteria, and lactic acid bacteria. Biosci Biotechnol Biochem. 2022 Sep 23;86(10):1467-1475. doi: 10.1093/bbb/zbac130. [PubMed:35904311 ]
- Melin LG, Dall JH, Lindholt JS, Steffensen LB, Beck HC, Elkrog SL, Clausen PD, Rasmussen LM, Stubbe J: Cycloastragenol Inhibits Experimental Abdominal Aortic Aneurysm Progression. Biomedicines. 2022 Feb 2;10(2):359. doi: 10.3390/biomedicines10020359. [PubMed:35203568 ]
- Bagalagel A, Diri R, Noor A, Almasri D, Bakhsh HT, Kutbi HI, Al-Gayyar MMH: The therapeutic effects of cycloastragenol in ulcerative colitis by modulating SphK/MIP-1alpha/miR-143 signalling. Basic Clin Pharmacol Toxicol. 2022 Nov;131(5):406-419. doi: 10.1111/bcpt.13788. Epub 2022 Sep 6. [PubMed:36029292 ]
- Yilmaz S, Bedir E, Ballar Kirmizibayrak P: The role of cycloastragenol at the intersection of NRF2/ARE, telomerase, and proteasome activity. Free Radic Biol Med. 2022 Aug 1;188:105-116. doi: 10.1016/j.freeradbiomed.2022.06.230. Epub 2022 Jun 17. [PubMed:35718303 ]
- Lin W, Yao H, Lai J, Zeng Y, Guo X, Lin S, Hu W, Chen J, Chen X: Cycloastragenol Confers Cerebral Protection after Subarachnoid Hemorrhage by Suppressing Oxidative Insults and Neuroinflammation via the SIRT1 Signaling Pathway. Oxid Med Cell Longev. 2022 Jun 2;2022:3099409. doi: 10.1155/2022/3099409. eCollection 2022. [PubMed:35693703 ]
- LOTUS database [Link]
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