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Year of first isolation: |
1999 |
| Formula: | C27H44O7 |
| Molecular weight: | 480 |
| Occurence in plants: |
Rhagodia baccata [https://en.wikipedia.org/wiki/Lygodium] »  ![Wikipedia: Rhagodia baccata [https://en.wikipedia.org/wiki/Lygodium]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(CCCC(C)(C)O)(CO)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](CO)(CCCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2S)-1,2,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 23657821 | InChiKey
[ ChemIDPlus: search ] | ICVFXEQYDYKIJU-VOCVGKOUSA-N | | InChI | InChI=1S/C27H44O7/c1-23(2,32)8-5-9-26(33,15-28)22-7-11-27(34)17-12-19(29)18-13-20(30)21(31)14-24(18,3)16(17)6-10-25(22,27)4/h12,16,18,20-22,28,30-34H,5-11,13-15H2,1-4H3/t16-,18-,20+,21-,22-,24+,25+,26+,27+/m0/s1 |
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| EI-MS m/z (relative intensity %) | | | HR-MS | | | LSI-MS (negative) m/z | 479 |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| C5D5N | | 01-Ha | 1.91 | | 01-He | 2.15 | | 02-Ha | 4.16 (m) | | 03-He | 4.21 (m) | | 04-Ha | 1.84 | | 04-He | 2.05 | | 05-H | 2.97 | | 07-H | 6.23 (d, 2.4) | | 09-H | 3.58 (m) | | 11-Ha | 1.71 | | 11-He | 1.89 | | 12-Ha | 2.60 (ddd, 13, 13, 5) | | 12-He | 2.00 | | 15-Ha | 2.15 | | 15-Hb | 1.96 | | 16-Ha | 2.47 | | 16-Hb | 2.19 | | 17-H | 3.10 (dd, 9.5, 9.5) | | 18-Me | 1.20 (s) | | 19-Me | 1.05 (s) | | 21-Ha | 4.25 (d, 10.7) | | 21-Hb | 4.05 (d, 10.7) | | 21-Me | ? | | 22-Ha | 1.65-2.10 (m) | | 22-Hb | 1.65-2.10 (m) | | 23-Ha | 1.65-2.10 (m) | | 23-Hb | 1.65-2.10 (m) | | 24-Ha | 1.65-2.10 (m) | | 24-Hb | 1.65-2.10 (m) | | 26-Me | 1.31 (s) | | 27-Me | 1.31 (s) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 242 nm (?) ; |
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| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC, semi-preparative column, 6% MeOH in CH2Cl2, Ret. 18.5 min (20E = 14.9 min) |
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Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-7M |
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Permanent link to this datasheet: 22-DEOXY-20,21-DIHYDROXYECDYSONE
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