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Year of first isolation: |
1982 |
| Formula: | C28H48O5 |
| Molecular weight: | 464 |
| Occurence in plants: |
Castanea (chestnut tree) insect galls [Fagaceae] »  ![Wikipedia: Castanea (chestnut tree) insect galls [Fagaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C)C(C)C(C(C(C)C1CCC2C1(CCC3C2CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@H](C[C@@H]([C@@H]1O)O)C(=O)CC1[C@@H]2CC[C@]2(C1CC[C@@H]2[C@H](C)[C@H]([C@@H](C(C(C)C)C)O)O)C)C » 
| | IUPAC Name | (2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | 80736-41-0 | | PubChem CID | 133534 | InChiKey
[ ChemIDPlus: search ] | VYUIKSFYFRVQLF-YLNAYWRASA-N | | InChI | nChI=1S/C28H48O5/c1-14(2)15(3)25(32)26(33)16(4)18-7-8-19-17-11-22(29)21-12-23(30)24(31)13-28(21,6)20(17)9-10-27(18,19)5/h14-21,23-26,30-33H,7-13H2,1-6H3/t15-,16-,17-,18+,19-,20-,21+,23-,24+,25+,26+,27+,28+/m0/s1 |
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| EI-MS m/z (relative intensity %) | 403 (0.4), 385 (0.3), 393 (3), 375 (2), 357 (2), 364 (100), 363 (35), 362 (36), 346 (42), 345 (59), 327 (36), 315 (7), 305 (5), 287 (17), 269 (10), 263 (11), 245 (13), 227 (5), 155 (5). | | HR-MS | | | FAB-MS m/z | 465 (M+1)+, 447 (M+1-18), 429, 393, 364 |
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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 | | | 28 | |
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| CDCl3 | | 01-Ha | | | 01-Hb | | | 02-H | 3.77 (br, w1/2=23) | | 03-H | 4.06 (br, w1/2= 8) | | 04-Ha | | | 04-He | | | 05-H | 2.69 (dd, 13, 4) | | 07-Ha | | | 07-Hb | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.69 (s ) | | 19-Me | 0.76 (s ) | | 22-H | 3.56 (d, 9)* | | 23-H | 3.72 (d, 9)* | | 24-Ha | | | 24-Hb | | | 25-H | | | Me' | 0.85 (d ) | | Me'' | 0.91 (d ) | | Me''' | 0.95 (d ) | | Me'''' | 0.97 (d ) |
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| M.P. | 259-261°C | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC on silica | Rf 0.38 (CHCl3-EtOH 6:1) | | GLC | GLC-MS of bismethane-boronate | | HPLC | NP-HPLC, Partisil 5 (CHCl3-iPrOH, gradient); RP-HPLC, Develosil ODS-3 (ACN-H2O 1:1) |
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Drosophila melanogaster BII cell assay: EC50 = >10-3M |
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Permanent link to this datasheet: CASTASTERONE
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