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Year of first isolation: |
1984 |
| Formula: | C29H46O7 |
| Molecular weight: | 506 |
| Occurence in plants: |
Silene praemixta [Caryophyllaceae] »  ![Wikipedia: Silene praemixta [Caryophyllaceae]](/images/wikipedia.png)
Silene otites [Caryophyllaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC(=O)OC1CCC2(C3CCC4(C(CCC4(C3=CC(=O)C2C1)O)C(C)(C(CCC(C)(C)O)O)O)C)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H](C1)OC(=O)C)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | [(3S,10R,13R,14S,17S)-14-hydroxy-10,13-dimethyl-6-oxo-17-[(2S,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate | | CAS-RN | | | PubChem CID | 11454959 | InChiKey
[ ChemIDPlus: search ] | JYZWBQULDMOHQE-DGRQGILPSA-N | | InChI | InChI=1S/C29H46O7/c1-17(30)36-18-7-12-26(4)19-8-13-27(5)23(28(6,34)24(32)10-11-25(2,3)33)9-14-29(27,35)20(19)16-22(31)21(26)15-18/h16,18-19,21,23-24,32-35H,7-15H2,1-6H3/t18-,19?,21?,23-,24+,26+,27+,28-,29+/m0/s1 |
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| CI-MS (NH3) m/z | 524(M+H+NH3)+, 507(M+H)+, 489 (M+H-H2O), 471 (M+H-2H2O), 453 (M+H-3H2O), 406 (524-C22-C27), 363 (507-C22-C27) | | EI-MS m/z (relative intensity %) | 470 (M - 2x18)+ (1), 455 (8), 389 (M - C22-C27)+ (100), 372 (96), 371 (96), 357 (23), 355 (22), 329 (22), 328 (85), 327 (24), 300 (95), 143 (96), 125 (96), 99 (97), 81 (96), 69 (96). |
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| C5D5N | | 01 | 29.5 | | 02 | 25.6 | | 03 | 68.3 | | 04 | 29.7 | | 05 | 52.1 | | 06 | 201.8 | | 07 | 121.2 | | 08 | 166.5 | | 09 | 34.2 | | 10 | 36.6 | | 11 | 21.5 | | 12 | 31.5 | | 13 | 48.5 | | 14 | 84.3 | | 15 | 32.2 | | 16 | 21.5 | | 17 | 50.1 | | 18 | 17.8 | | 19 | 24.1 | | 20 | 76.8 | | 21 | 21.5 | | 22 | 77.5 | | 23 | 27.4 | | 24 | 42.6 | | 25 | 69.5 | | 26 | 30.0 | | 27 | 30.0 | | CH3- | 21.1 | | O-C=O | 170.0 |
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| C5D5N | | -O Ac | 2.00 (s ) | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | 5.03 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.23 (d, 2.4) | | 09-Ha | 3.46 (m, w1/2=23) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.23 (s ) | | 19-Me | 1.02 (s ) | | 21-Me | 1.62 (s ) | | 22-Hb | 3.91 (d, 9.2) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.39 (s ) | | 27-Me | 1.39 (s ) |
| C5D5N* | | -O Ac | | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | 5.01 (br, s) | | 04-Ha | | | 04-He | | | 05-H | 2.58 | | 07-H | 6.22 (br, s) | | 09-Ha | 3.44 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.02 (t, 9.1) | | 18-Me | 1.21 (s ) | | 19-Me | 0.99 (s ) | | 21-Me | 1.59 (s ) | | 22-Hb | 3.88 (br, d, 10.1) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.37 (s ) | | 27-Me | 1.37 (s ) |
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| M.P. | 150-152 °C | | [α]D28 | + 72.1 ? 2 ° (c 0.70; MeOH) | | IR (KBr) ν max (cm-1) | 3450 (OH), 1740, 1655 (cyclohexenone), 1255 | | UV (EtOH) λ max (log ε) | 246 (4.01) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC, Zorbax-SIL 25 cm x 4.6 mm i.d., solvent cyclohexane-iPrOH-H2O 100:30:1.5 v/v/v, flow-rate 1 ml.min-1, Ret. 11.0 min (2d20E 18.8 min); Zorbax-SIL 25 cm x 9.4 mm i.d., solvent CH2Cl2-PrOH-H2O 125:15:1 v/v/v, flow-rate 4 ml.min-1, Ret. 15.1 min. |
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Drosophila melanogaster BII cell assay: EC50 = 4.3 x 10-6M |
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Permanent link to this datasheet: 2-DEOXY-20-HYDROXYECDYSONE 3-ACETATE
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