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Year of first isolation: |
1985 |
| Formula: | C27H44O9 |
| Molecular weight: | 512 |
| Occurence in plants: |
Silene nutans [Caryophyllaceae] »  ![Wikipedia: Silene nutans [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(CC(C(C)(C)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](O)CC(C(C)(C)O)O)O)O)C)C)O » 
[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](O)C[C@H](C(C)(C)O)O)O)O)C)C)O »
[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](O)C[C@@H](C(C)(C)O)O)O)O)C)C)O »
| | IUPAC Name | (1S,2S,3R,5R,9S,10R,13R,14S,17S)-1,2,3,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,5,6-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 13799583 | InChiKey
[ ChemIDPlus: search ] | GHCGVFIICXLSSM-ALZVWQKOSA-N | | InChI | InChI=1S/C27H44O9/c1-23(2,34)19(30)12-20(31)26(5,35)18-7-9-27(36)14-10-16(28)15-11-17(29)21(32)22(33)25(15,4)13(14)6-8-24(18,27)3/h10,13,15,17-22,29-36H,6-9,11-12H2,1-5H3/t13-,15+,17-,18+,19?,20-,21+,22-,24-,25-,26-,27-/m1/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 512 (M)+(0), 495 (M+H - 18)+(1), 476 (2), 458 (10), 440 (4), 425 (6), 391 (3), 379 (M - C22-C27)+ (4), 369 (2), 368 (M - C24-C27 - 3x18)+ (5), 367 (2), 361 (15), 360 (11), 344 (25), 343 (24), 326 (35), 325 (27), 316 (M - C20-C27 - 18)+ (25), 301 (17), 300 (23), 299 (15), 283 (21), 281 (21), 115 (C22-C27-18)+ (60), 97 (100). | | 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 | 4.10 (m ) | | 02-Ha | 4.10 (m ) | | 03-He | 4.10 (m ) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 6.12 | | 09-Ha | 3.51 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.91 (s ) | | 19-Me | 1.32 (s ) | | 21-Me | 1.42 (s ) | | 22-H | 3.69-3.74 (m ) | | 23-Ha | | | 23-Hb | | | 24-H | 3.69-3.74 (m ) | | 26-Me | 0.98 (s )* | | 27-Me | 1.04 (s )* |
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| M.P. | 218-219 °C | | [α]D28 | +111.2 ? 2 ° (c 0.37; MeOH) | | IR (KBr) ν max (cm-1) | 3350-3450 (OH), 1660 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 244 (4.09) |
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Galleria mellonella in vivo assay: ED50 = 12.5 ug/g | Sarcophaga bullata in vivo assay: ED50 = 52.0 ug/g |
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Permanent link to this datasheet: NUSILSTERONE
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