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Year of first isolation: |
1995 |
| Formula: | C32H47O8N |
| Molecular weight: | 573 |
| Occurence in plants: |
Vitex canescens [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Vitex canescens [Lamiaceae (alt. Labiatae)]](/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)(CCC(C(C)(C)O)OC(=O)C5=CC=CN5)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)(CCC(C(C)(C)O)OC(=O)c1ccc[nH]1)O)O)C)C » 
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)(CC[C@@H](C(C)(C)O)OC(=O)c1ccc[nH]1)O)O)C)C »
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)(CC[C@H](C(C)(C)O)OC(=O)c1ccc[nH]1)O)O)C)C »
| | IUPAC Name | [(6S)-2,6-dihydroxy-2-methyl-6-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptan-3-yl] 1H-pyrrole-2-carboxylate | | CAS-RN | | | PubChem CID | 10438055 | InChiKey
[ ChemIDPlus: search ] | AVXVGYYNQOOFRN-WBKALDGLSA-N | | InChI | InChI=1S/C32H47NO8/c1-28(2,38)26(41-27(37)21-7-6-14-33-21)10-12-31(5,39)25-9-13-32(40)19-15-22(34)20-16-23(35)24(36)17-29(20,3)18(19)8-11-30(25,32)4/h6-7,14-15,18,20,23-26,33,35-36,38-40H,8-13,16-17H2,1-5H3/t18-,20-,23+,24-,25-,26?,29+,30+,31-,32+/m0/s1 |
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| HR-MS | | | EI-MS m/z (relative intensity %) | 444 [M+H-COC4H4N-2H2O]+ (2), 426 (2), 411 (3), 393 (2), 363 (1), 345 (3), 327 (5), 309 (1), 391 (1), 211 (6), 210 (6), 209 (5), 193 (4), 192 (1), 191 (4), 183 (4), 182 (1), 143 (81), 125 (100), 111 (88), 109 (15), 107 (26), 94 (72), 93 (82), 67 (21), 66 (19), 65 (23) | | EI-MS m/z | | | ES-MS m/z (relative intensity %) | 597 [M+H+Na]+ (8), 596 [M+Na]+ (25) |
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| C5D5N | | 01 | 37.9 | | 02 | 68.1 a | | 03 | 68.0 a | | 04 | 32.4 | | 05 | 51.3 | | 06 | 203.5 | | 07 | 121.5 | | 08 | 166.1 | | 09 | 34.3 | | 10 | 38.5 | | 11 | 20.9 b | | 12 | 31.7 c | | 13 | 47.3 | | 14 | 84.3 | | 15 | 31.4 c | | 16 | 21.9 b | | 17 | 53.0 | | 18 | 17.8 | | 19 | 24.3 | | 20 | 74.0 d | | 21 | 25.6 | | 22 | 41.7 | | 23 | 25.0 | | 24 | 80.6 | | 25 | 71.7 d | | 26 | 27.3 | | 27 | 26.9 | | COO | 161.9 | | p-2' | 123.9 | | p-3' | 115.9 e | | p-4' | 110.2 e | | p-5' | 124.1 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 4.15 (br d, 8.6) | | 03-He | 4.23 (br s ) | | 04-Ha | | | 04-He | | | 05-H | 3.00 (dd, 13.4, 3.8) | | 07-H | 6.19 (d, 2) | | 09-Ha | 3.53 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.90 (t, 9.4) | | 18-Me | 1.04 (s ) | | 19-Me | 1.02 (s ) | | 21-Me | 1.50 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-H | 5.58 (br d, 8.9) | | 26-Me | 1.42 (s ) | | 27-Me | 1.44 (s ) | | p-1' | 13.30 (br s) | | p-3' | 7.28 (m ) | | p-4' | 6.40 (m ) | | p-5' | 7.28 (m ) |
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| M.P. | 152-153 °C | | [α]D26 | + 18.8 ° (c 0.09; MeOH) | | IR (KBr) ν max (cm-1) | 3412 (OH), 1683 (CO), 1643 (cyclohexenone) | | UV (EtOH) λ max (log ε) | 240 sh (4.10), 259 (4.18) |
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Drosophila melanogaster BII cell assay: EC50 = 5.3 x 10-10M | Musca assay: 84% (20-hydroxyecdysone = 100%) |
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Permanent link to this datasheet: CANESCENSTERONE
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