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Year of first isolation: |
1981 |
| 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)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 ] | 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@](C)([C@@H](CCC(C)(C)O)O[C@@H]1C(C([C@H](C(O1)CO)O)O)O)O)O)C)C » 
| | IUPAC Name | (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]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 81655-86-9 | | PubChem CID | 196202 | InChiKey
[ ChemIDPlus: search ] | OYLAWXRQIJWVHG-PRYDOBOQSA-N | | InChI | InChI=1S/C33H54O12/c1-29(2,41)9-8-24(45-28-27(40)26(39)25(38)22(15-34)44-28)32(5,42)23-7-11-33(43)17-12-19(35)18-13-20(36)21(37)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 %) | 623 (M-18)+ (0.3), 606 (0.8), 588 (0.5), 570 (0.2), 489 (1.1), 473 (2.0), 463 (2.2), 455 (3.8), 445 (5), 444 (4), 427 (34), 426 (35), 409 (12), 408 (11), 393 (3.8), 363 (3.7), 358 (5), 352 (17), 345 (100), 344 (94), 327 (67), 309 (22), 300 (34), 163 (20), 145 (22), 142 (33), 99 (66), 81 (44), 69 (42). | | 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 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 4.0-4.2 | | 03-He | 4.0-4.2 | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.11 | | 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 | 1.09 | | 19-Me | 0.90 | | 21-Me | 1.49 | | 22-H | 3.59 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.24 | | 27-Me | 1.30 |
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| M.P. | 254-256 °C | | [α]D22 | + 93.1 ? 2 ° (c 1.02; MeOH) | | IR (KBr) ν max (cm-1) | 3370-3440 (OH), 1645 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 246 (4.15) |
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Drosophila melanogaster BII cell assay: EC50 = 4.1 x 10-5M |
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Permanent link to this datasheet: SILENEOSIDE A
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