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Year of first isolation: |
1971 |
| Formula: | C27H42O4 |
| Molecular weight: | 430 |
| Occurence in plants: |
Polypodium vulgare [Polypodiaceae] »  ![Wikipedia: Polypodium vulgare [Polypodiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1CCC(OC1O)C(C)C2CCC3C2(CCC4C3=CC(=O)C5C4(CCC(C5)O)C)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H]([C@H]1CC[C@@H]([C@H](O1)O)C)C)C)C » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14R,17R)-3-hydroxy-17-[(1S)-1-(6-hydroxy-5-methyloxan-2-yl)ethyl]-10,13-dimethyl-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101306873 | InChiKey
[ ChemIDPlus: search ] | FCMDISUJEUTJIU-KBBSIBECSA-N | | InChI | InChI=1S/C27H42O4/c1-15-5-8-24(31-25(15)30)16(2)19-6-7-20-18-14-23(29)22-13-17(28)9-11-27(22,4)21(18)10-12-26(19,20)3/h14-17,19-22,24-25,28,30H,5-13H2,1-4H3/t15?,16-,17-,19+,20-,21-,22-,24?,25?,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z | 430 (M)+ | | ES-MS m/z (relative intensity %) | MS of 26-OMe deriv.: 444 (7, M)+, 413 (21, M-OMe), 412 (33, M-MeOH), 384 (21, M-MeOH-CO), 342 (30), 316 (78), 287 (32, M- side chain), 285 (44), 261 (26), 129 (100), 97 (33). |
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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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| DMSO-d6 | | comp. | native 26-Ome | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.7 | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.57 (s ) 0.86 (s ) | | 19-Me | 0.75 (s ) 0.65 (s ) | | 21-Me | 0.98 (d, 7) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-H | | | 27-Me | 0.98 (d, 7) |
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| M.P. | 162-164 °C ; | | [α]D25 | + 6.6 ° (c 0.50; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | | | LC on silica | (elution with CHCl3, then CHCl3-MeOH 50:1) |
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Permanent link to this datasheet: POLYPODOGENIN
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