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Year of first isolation: |
1969 |
| Formula: | C27H42O6 |
| Molecular weight: | 462 |
| Occurence in plants: |
Podocarpus elatus [Podocarpaceae] »  ![Wikipedia: Podocarpus elatus [Podocarpaceae]](/images/wikipedia.png)
Pfaffia iresinoides [Amaranthaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3=C(C1=CCC2C(C)(C(CCC(C)(C)O)O)O)CC(=O)C4C3(CC(C(C4)O)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)CC1=C2CC[C@]2(C1=CC[C@@H]2[C@@]([C@@H](CCC(C)(C)O)O)(C)O)C)C » 
| | IUPAC Name | (2S,3R,5R,10S,13R,17S)-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | 22612-27-7 | | PubChem CID | 441831 | InChiKey
[ ChemIDPlus: search ] | AEFMTBQZWMUASH-IILZZRPCSA-N | | InChI | InChI=1S/C27H42O6/c1-24(2,32)10-9-23(31)27(5,33)22-7-6-16-15-12-19(28)18-13-20(29)21(30)14-26(18,4)17(15)8-11-25(16,22)3/h6,18,20-23,29-33H,7-14H2,1-5H3/t18-,20+,21-,22-,23+,25-,26+,27+/m0/s1 |
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| EI-MS m/z (relative intensity %) | 444 (M -18)+, 344, 327, 300, 99, 81 | | FAB-MS m/z | 463 (M+H)+ | | HR-MS | |
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| C5D5N | | 01 | 38.6 | | 02 | 69.6 | | 03 | 68.3 | | 04 | 32.9 | | 05 | 53.6 | | 06 | 212.4 | | 07 | 39.4 | | 08 | 122.9 | | 09 | 136.4 | | 10 | 43.6 | | 11 | 23.0 | | 12 | 37.5 | | 13 | 46.6 | | 14 | 148.9 | | 15 | 119.5 | | 16 | 31.5 | | 17 | 57.0 | | 18 | 18.7 | | 19 | 29.6 | | 20 | 76.2 | | 21 | 20.8 | | 22 | 77.7 | | 23 | 27.4 | | 24 | 42.7 | | 25 | 69.7 | | 26 | 30.0 | | 27 | 30.7 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | 3.92 (br dt, 12.4, 3.0) | | 03-He | 4.46 (br s ) | | 04-Ha | | | 04-He | | | 05-H | 3.04 (dd, 12.4, 4.0) | | 07-Ha | 2.90 (br d, 21) | | 07-Hb | 3.44 (br d, 21) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-H | 5.43 (br s ) | | 16-Ha | 3.01 (br dd, 16.0, 10.6) | | 16-Hb | | | 17-H | | | 18-Me | 1.35 (s ) | | 19-Me | 1.07 (s ) | | 21-Me | 1.55 (s ) | | 22-H | 3.86 (br d, 8.2) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.43 (s ) | | 27-Me | 1.44 (s ) |
| CD3OD | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-Ha | | | 07-Hb | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-H | 5.38 | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.04 | | 19-Me | 0.98 | | 21-Me | 1.23 | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.17 | | 27-Me | 1.17 |
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| M.P. | 125-127 °C | | [α]D15 | -15.7 ° (c 1.1; MeOH) | | IR (KBr) ν max (cm-1) | 3400 (OH), 1710 (CO), 1650 | | UV (EtOH) λ max (log ε) | 244 (4.14) |
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| HPTLC | NP-TLC on silica gel : Rf 0.45 (CHCl3-EtOH 4:1) | | TLC | | | GLC | | | HPLC | |
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Drosophila melanogaster BII cell assay: EC50 = 1.2 x 10-5M | Calliphora assay: 20% (20-hydroxyecdysone = 100%) |
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Permanent link to this datasheet: PODECDYSONE B
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