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Year of first isolation: |
1982 |
| Formula: | C33H54O13 |
| Molecular weight: | 658 |
| 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(C(C(C(C4)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)OC5C(C(C(C(O5)CO)O)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | [C@@H]1([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@](C)([C@@H](CCC(C)(C)O)O[C@@H]1C(C([C@H](C(O1)CO)O)O)O)O)O)C)C)O » 
| | IUPAC Name | (1S,2R,3R,5R,9R,10R,13R,17S)-17-[(2R,3R)-2,6-dihydroxy-6-methyl-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-1,2,3,14-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 83207-65-2 | | PubChem CID | 196245 | InChiKey
[ ChemIDPlus: search ] | IOJDAWSWQWSBHN-JRCWSXPQSA-N | | InChI | InChI=1S/C33H54O13/c1-29(2,42)9-8-22(46-28-26(40)25(39)24(38)20(14-34)45-28)32(5,43)21-7-11-33(44)16-12-18(35)17-13-19(36)23(37)27(41)31(17,4)15(16)6-10-30(21,33)3/h12,15,17,19-28,34,36-44H,6-11,13-14H2,1-5H3/t15-,17-,19+,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 %) | 460 (M - 180 - 18)+ (0.6), 442 (4), 427 (4), 424 (2), 368 (2), 361 (4), 360 (4), 343 (8), 325 (4), 316 (4), 309 (2), 301 (2), 163 (3), 145 (4), 143 (6), 125 (5), 99 (100), 81 (98). | | HR-MS | |
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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 | 90.76* | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| C5D5N | | 01-Hb | 4.13 | | 02-Ha | 4.13 | | 03-He | 4.13 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.06 | | 09-Ha | 3.41 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.11 | | 19-Me | 1.26 | | 21-Me | 1.48 | | 22-H | 3.58 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.24 | | 27-Me | 1.29 | | H-1' | 5.46 (d, 3.3) |
| C5D5N (hepta-OAc) | | 01-Hb | 5.30-5.75 | | 02-Ha | 5.30-5.75 | | 03-He | 5.30-5.75 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.01 | | 09-Ha | 3.42 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.97 | | 19-Me | 1.03 | | 21-Me | 1.39 | | 22-H | 3.64 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.31 | | 27-Me | 1.31 | | H-1' | 5.80 |
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| M.P. | 232-234 °C | | [α]D22 | + 48.0 ? 2 ° (c 1.02; MeOH) | | IR (KBr) ν max (cm-1) | 3370-3440 (OH), 1658 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 2.45 (4.01) |
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Drosophila melanogaster BII cell assay: EC50 = 1.0 x 10-4M |
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Permanent link to this datasheet: SILENEOSIDE C
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