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Year of first isolation: |
2007 |
| Formula: | C28H44O6 |
| Molecular weight: | 476 |
| Occurence in plants: |
Polyporus umbellatus [Fungi] »  ![Wikipedia: Polyporus umbellatus [Fungi]](/images/wikipedia.png)
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| Occurence in animals: |
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![23,26-EPOXY-3,14,20,22-TETRAHYDROXY-ERGOST-7-EN-6-ONE [= POLYPORUSTERONE-I]](images/ecdy/420.gif)
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| Canonical SMILES | CC1COC(C1C)C(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CCC(C5)O)C)C)O)O)O | 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@]1(CC[C@@H]2[C@](O)([C@@H]([C@H]1[C@@H]([C@H](CO1)C)C)O)C)O)C)C » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14S,17S)-17-[(1R,2S)-1-[(2R,3R,4R)-3,4-dimethyloxolan-2-yl]-1,2-dihydroxypropan-2-yl]-3,14-dihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 102322637 | InChiKey
[ ChemIDPlus: search ] | FBQJWZJYUOWAOR-UBTGPEGFSA-N | | InChI | InChI=1S/C28H44O6/c1-15-14-34-23(16(15)2)24(31)27(5,32)22-8-11-28(33)19-13-21(30)20-12-17(29)6-9-25(20,3)18(19)7-10-26(22,28)4/h13,15-18,20,22-24,29,31-33H,6-12,14H2,1-5H3/t15-,16+,17-,18-,20-,22-,23+,24+,25+,26+,27-,28+/m0/s1 |
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| EI-MS m/z (relative intensity %) | 476 [M]+ (2), 458 (11), 440 (8), 422 (3), 407 (1), 347 (57), 329 (71), 311 (34), 295 (6), 287 (18), 269 (21), 99 (100), 81 (12) | | CI-MS (NH3) m/z | | | HR-FAB-MS (positive) | 499.3033 [M+Na]+ (calculated for C28H44O6Na : 499.3030) |
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| C5D5N | | 01 | 36.8 | | 02 | 29.2 | | 03 | 64.0 | | 04 | 34.2 | | 05 | 51.6 | | 06 | 203.9 | | 07 | 121.1 | | 08 | 166.6 | | 09 | 33.5 | | 10 | 37.2 | | 11 | 21.5 | | 12 | 32.1 | | 13 | 48.0 | | 14 | 84.1 | | 15 | 31.5 | | 16 | 21.8 | | 17 | 49.8 | | 18 | 18.0 | | 19 | 24.2 | | 20 | 76.7 | | 21 | 22.9 | | 22 | 79.3 | | 23 | 86.9 | | 24 | 46.9 | | 25 | 42.5 | | 26 | 74.3 | | 27 | 15.3 | | 28 | 18.0 |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | 4.12 (br, s) | | 04-Ha | | | 04-He | | | 05-H | 2.98 (m) | | 07-H | 6.26 (br, s) | | 09-H | 3.56 (br, s) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.47 (m) | | 16-Hb | 2.30 (m) | | 17-H | 3.46 (d, 9.1) | | 18-Me | 1.23 (s) | | 19-Me | 1.05 (s) | | 21-Me | 1.70 (s) | | 22-H | 3.89 (m) | | 23-H | 3.89 (m) | | 24-H | 1.94 (m) | | 25-H | 1.70 (m) | | 26-CH2OH | 3.89 (m), 3.38 (m) | | 27-Me | 0.87 (d, 6.6) | | 28-Me | 1.27 (d, 6.5) |
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| M.P. | °C ; | | [α]D20 | + 65.7 ° (c 0.39; MeOH) | | IR (KBr) ν max (cm-1) | 3350 (OH), 1650 (C=O) | | UV (MeOH) λ max (log ε) | 242 (3.98) ; |
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| HPLC | RP-HPLC column Phenomenex ODS (250 x 10 mm), solvent 30% MeCN, Flow-rate 2 ml/min, Ret 42.4 min. | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 23,26-EPOXY-3,14,20,22-TETRAHYDROXY-ERGOST-7-EN-6-ONE [= POLYPORUSTERONE-I]
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