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Year of first isolation: |
1998 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Axyris amaranthoides [https://en.wikipedia.org/wiki/Lygodium] »  ![Wikipedia: Axyris amaranthoides [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(C(C(C(C4)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3([C@H]([C@@H]([C@@H](C4)O)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O » 
| | IUPAC Name | (1R,2R,3R,5R,9R,10R,13R,14S,17S)-1,2,3,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-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 | 10625088 | InChiKey
[ ChemIDPlus: search ] | VJRBXZFHKYDEQV-HACZXUJGSA-N | | InChI | InChI=1S/C27H44O8/c1-23(2,33)9-8-20(30)26(5,34)19-7-11-27(35)15-12-17(28)16-13-18(29)21(31)22(32)25(16,4)14(15)6-10-24(19,27)3/h12,14,16,18-22,29-35H,6-11,13H2,1-5H3/t14-,16-,18+,19-,20+,21+,22-,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | LSI-MS | 495 [M-H] - |
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| C5D5N | | 01 | 76.2 | | 02 | 68.1 | | 03 | 70.5 | | 04 | 33.0 | | 05 | 46.4 | | 06 | -- | | 07 | 121.6 | | 08 | -- | | 09 | 35.0 | | 10 | 42.0 | | 11 | 21.4 | | 12 | 32.0 | | 13 | 47.0 | | 14 | 84.2 | | 15 | 31.5 | | 16 | 21.5 | | 17 | 50.1 | | 18 | 17.8 | | 19 | 20.3 | | 20 | 76.8 | | 21 | 21.6 | | 22 | 77.5 | | 23 | 27.5 | | 24 | 42.6 | | 25 | 69.5 | | 26 | 30.0 | | 27 | 30.1 |
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| CD3OD | | 01-Ha | 4.31 (bs) | | 02-Ha | 4.29 (m) | | 03-He | 4.30 (m) | | 04-Ha | 1.85 | | 04-He | 2.10 | | 05-H | 3.30 | | 07-H | 6.30 (d: 2.5) | | 09-H | 3.60 (m) | | 11-Ha | 1.76 | | 11-He | 1.89 | | 12-Ha | 2.60 (dd: 13, 5) | | 12-He | 2.00 | | 15-Ha | 2.20 | | 15-Hb | 1.90 | | 16-Ha | 2.46 | | 16-Hb | 2.10 | | 17-H | 3.01 (t: 8) | | 18-Me | 1.25 (s) | | 19-Me | 1.44 (s) | | 21-Me | 1.59 (s) | | 22-H | 3.87 (m) | | 23-Ha | 1.84 | | 23-Hb | 2.14 | | 24-Ha | 2.30 | | 24-Hb | 1.85 | | 26-Me | 1.38 (s) | | 27-Me | 1.38 (s) |
| C5D5N | | 01-Ha | 3.82 (bs, w1/2 6.8) | | 02-Ha | 3.87 (bt) | | 03-He | 4.03 (m) | | 04-Ha | 1.70 | | 04-He | 1.80 | | 05-H | 2.60 (dd: 13, 4) | | 07-H | 5.82 (d: 2.3) | | 09-H | 3.07 (m) | | 11-Ha | 1.70 | | 11-He | 1.80 | | 12-Ha | 2.14 (dd: 13, 5) | | 12-He | 1.82 | | 15-Ha | 2.01 | | 15-Hb | 1.57 | | 16-Ha | 1.95 | | 16-Hb | 1.76 | | 17-H | 2.38 (t, 8) | | 18-Me | 0.90 (s) | | 19-Me | 1.08 (s) | | 21-Me | 1.19 (s) | | 22-H | 3.33 | | 23-Ha | 1.32 | | 23-Hb | 1.65 | | 24-Ha | 1.75 | | 24-Hb | 1.43 | | 26-Me | 1.20 (s) | | 27-Me | 1.20 (s) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 240.6 (4.00) ; |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC - C6 semi-preparative column eluted with 35% MeOH in water, flow-rate 2 mL/min, Ret 21.0 min; 20E 24.2 min) |
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Drosophila melanogaster BII cell assay: EC50 = 2.5 x 10-7M |
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Permanent link to this datasheet: (20R)-1α,20-DIHYDROXYECDYSONE
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