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Year of first isolation: |
1986 |
| Formula: | C33H54O10 |
| Molecular weight: | 610 |
| Occurence in plants: |
Blechnum minus [Blechnaceae] »  ![Wikipedia: Blechnum minus [Blechnaceae]](/images/wikipedia.png)
Silene brahuica [Caryophyllaceae] »
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| Occurence in animals: |
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![BLECHNOSIDE A [= SILENOSIDE E]](images/ecdy/170.gif)
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)O)C(CCC(C)(C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H](C1)O[C@H]1C([C@@H](C(C(O1)CO)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)O)C)C » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 21626688 | InChiKey
[ ChemIDPlus: search ] | KIYBOATYEXVQQC-LJFUCLFESA-N | | InChI | InChI=1S/C33H54O10/c1-17(23(35)9-10-30(2,3)40)19-8-13-33(41)21-15-24(36)22-14-18(6-11-31(22,4)20(21)7-12-32(19,33)5)42-29-28(39)27(38)26(37)25(16-34)43-29/h15,17-20,22-23,25-29,34-35,37-41H,6-14,16H2,1-5H3/t17-,18-,19+,20-,22-,23+,25+,26+,27-,28+,29+,31+,32+,33+/m0/s1 |
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| DEI m/z (relative intenzity %) | DCI-MS gives a parent ion at m/z 611 [M+1] (0.4%); 431 [M+1-glucose] (10%) | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| C5D5N | | 01 | 29.9 * | | 02 | 29.5 * | | 03 | 72.5 | | 04 | 27.6 * | | 05 | 51.5 | | 06 | 203.0 | | 07 | 121.3 | | 08 | 165.9 | | 09 | 34.7 | | 10 | 36.8 | | 11 | 21.6 | | 12 | 31.8 | | 13 | 48.2 | | 14 | 84.1 | | 15 | 31.8 | | 16 | 26.8 | | 17 | 48.4 | | 18 | 15.9 | | 19 | 24.0 | | 20 | 43.0 | | 21 | 13.7 | | 22 | 74.1 | | 23 | 25.8 | | 24 | 42.5 | | 25 | 69.8 | | 26 | 30.0 | | 27 | 30.3 | | glu-1 | 103.3 | | glu-2 | 75.3 | | glu-3 | 78.3 | | glu-4 | 71.9 | | glu-5 | 78.7 | | glu-6 | 63.0 |
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| C5D5N | | 01-Ha | | | 02-Ha | | | 02-He | | | 03-He | 3.84 | | 04-Ha | | | 04-He | | | 05-H | 2.89 | | 07-H | 6.17 (d ) | | 09-Ha | 3.44 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.68 (s ) | | 19-Me | 0.83 (s ) | | 21-Me | 1.27 (d , 6.5) | | 22-Hb | 4.10 | | 23-Ha | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.37 (s ) | | 27-Me | 1.37 (s ) | | glu sign.: | | | glu- 1H | 4.86 (d, 7.5) | | glu-(2-6)H | 4.0 - 4.5 |
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| M.P. | 195-196 °C | | [α]D20 | + 44.4 ? 2° (c 0.80; MeOH) | | IR (KBr) ν max (cm-1) | 3380-3430 (OH), 1655 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 245 (4.0) - 243 (4.02) |
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| HPTLC | | | TLC | Silica Rf 0.2 (vanillin spray gives a blue/green spot) [CHCl3-EtOH 80:20] | | GLC | | | HPLC | NP-HPLC on Spherisorb S GP (50 cm x 8 mm) solvent CHCl3-EtOH (88:12) |
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Drosophila melanogaster BII cell assay: inactive |
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Permanent link to this datasheet: BLECHNOSIDE A [= SILENOSIDE E]
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