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Year of first isolation: |
1984 |
| Formula: | C33H54O12 |
| Molecular weight: | 642 |
| Occurence in plants: |
Silene brahuica [Caryophyllaceae] »  ![Wikipedia: Silene brahuica [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O[C@H]1C(C([C@H](C(O1)CO)O)O)O)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 | (2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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 | 93552-68-2 | | PubChem CID | 21768882 | InChiKey
[ ChemIDPlus: search ] | APFXLSITBUTSAO-SDNJJZGQSA-N | | InChI | InChI=1S/C33H54O12/c1-29(2,41)9-8-24(37)32(5,42)23-7-11-33(43)17-12-19(35)18-13-21(44-28-27(40)26(39)25(38)22(15-34)45-28)20(36)14-30(18,3)16(17)6-10-31(23,33)4/h12,16,18,20-28,34,36-43H,6-11,13-15H2,1-5H3/t16-,18-,20-,21+,22+,23-,24+,25-,26-,27+,28-,30+,31+,32+,33+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 624 (M-18)+ (0.5), 606 (0.8), 588 (5), 570 (1), 514 (0.8), 507 (0.7), 490 (0.9), 473 (0.6), 462 (1), 444 (1), 426 (11), 411 (2), 408 (3), 393 (1), 375 (1), 363 (5), 345 (55), 327 (13), 309 (10), 300 (11), 284 (11), 145 (10), 143 (12), 135 (11), 99 (100), 81 (55), 69 (53). | | HR-MS | |
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| C5D5N | | 01 | | | 02 | 68.0 | | 03 | 79.0 * | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | 84.2 | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | 76.8 | | 21 | | | 22 | 77.5 | | 23 | | | 24 | | | 25 | 69.6 | | 26 | | | 27 | | | s1' | 103.5 | | s2' | 70.9 | | s3' | 71.6 | | s4' | 70.9 | | s5' | 73.3 | | s6' | 62.5 |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 3.96 (m ) | | 03-He | 3.96 (m ) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.10 | | 09-Ha | 3.37 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.09 | | 19-Me | 0.86 | | 21-Me | 1.48 | | 22-H | 3.75 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.25 | | 27-Me | 1.25 | | H-1' | 5.48 (d, 3.9) |
| CDCl3 (hepta-OAc) | | 01-Ha | | | 01-He | | | 02-Ha | 5.13 (m, w1/2=21) | | 03-He | 4.09 (m, w1/2=8) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.07 | | 09-Ha | 3.49 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.01 | | 19-Me | 0.89 | | 21-Me | 1.49 | | 22-H | 5.29 (d br ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.32 | | 27-Me | 1.33 | | H-1' | 5.63 (d, 3.6) |
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| M.P. | 240-242 °C | | [α]D20 | + 91.2 ? 2 ° (c 1.01; MeOH) | | IR (KBr) ν max (cm-1) | 3380-3430 (OH), 1648 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 247 (4.15) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | | | LC | silicagel with CHCl3-MeOH (4:1, v/v) |
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Drosophila melanogaster BII cell assay: EC50 = 3.0 x 10-5M |
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Permanent link to this datasheet: SILENEOSIDE D
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