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Year of first isolation: |
1995 |
| Formula: | C28H44O8 |
| Molecular weight: | 508 |
| Occurence in plants: |
Paxillus atrotomentosus [Fungi] »  ![Wikipedia: Paxillus atrotomentosus [Fungi]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CC(C3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CC(=C)C(C)(C)O)O)O)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]2[C@@H](C[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC(=C)C(C)(C)O)O)O)O)C)O)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methyl-5-methylideneheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 15839579 | InChiKey
[ ChemIDPlus: search ] | NDWGRONXKHTPNQ-VCSIHVNPSA-N | | InChI | InChI=1S/C28H44O8/c1-14(24(2,3)34)9-22(33)27(6,35)21-7-8-28(36)16-11-17(29)15-10-18(30)19(31)12-25(15,4)23(16)20(32)13-26(21,28)5/h11,15,18-23,30-36H,1,7-10,12-13H2,2-6H3/t15-,18+,19-,20+,21-,22+,23+,25-,26+,27+,28+/m0/s1 |
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| EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 531 (M+Na)+ (3), 509 (M+H)+ (1), 491 (2), 473 (3), 455 (4), 437 (2), 345 (5), 317 (7), 299 (12), 239 (18), 121 (49), 105 (51), 91 (87), 81 (63), 69 (70), 55 (100) |
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| CD3OD | | 01 | 39.08 | | 02 | 68.96 | | 03 | 68.59 | | 04 | 33.28 | | 05 | 52.78 | | 06 | 206.72 | | 07 | 122.77 | | 08 | 165.71 | | 09 | 42.94 | | 10 | 39.90 | | 11 | 69.51 | | 12 | 43.77 | | 13 | a | | 14 | 84.93 | | 15 | 31.85 | | 16 | 21.56 | | 17 | 50.30 | | 18 | 18.89 | | 19 | 24.60 | | 20 | 77.72 | | 21 | 20.98 | | 22 | 78.02 | | 23 | 34.59 | | 24 | 155.34 | | 25 | 73.63 | | 26 | 30.21 | | 27 | 29.76 | | 28 | 110.42 |
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| CD3OD | | 01-Ha | 1.38 (dd, 12.8, 12.0) | | 01-He | 2.59 (dd, 12.8, 4.2) | | 02-Ha | 4.01 (ddd, 12.0, 4.2, 3.3) | | 03-He | 3.95 (q ) | | 04-Ha | 1.78 (ddd, 14.0, 13.0, 2.5) | | 04-He | 1.69 (ddd, 14.0, 3.8, 3.0) | | 05-H | 2.34 (dd, 13.0, 3.8) | | 07-H | 5.81 (bd, 2.7) | | 09-H | 3.15 (dd, 2.7, 9.0) | | 11-Ha | 4.11 (ddd, 10.5, 9.0, 6.0) | | 12-Ha | 2.23 (dd, 12.0, 10.5) | | 12-He | 2.17 (dd, 12.0, 6.0) | | 15-Ha | 1.97 (m ) | | 15-Hb | 1.59 (m ) | | 16-Ha | 2.04 (m ) | | 16-Hb | 1.82 (m ) | | 17-H | 2.46 (dd, 9.5, 8.7) | | 18-Me | 0.885 (s ) | | 19-Me | 1.060 (s ) | | 21-Me | 1.256 (s ) | | 22-H | 3.58 (dd, 10.6, 1.8) | | 23-Ha | 2.39 (bdd, 14.5, 1.8) | | 23-Hb | 2.14 (dd, 14.5, 10.6) | | 26-Me | 1.376 (s ) | | 27-Me | 1.323 (s ) | | 28-CH2= | 5.14 (bs), 4.96 (bs) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3406 (OH), 1657 (cyclohexenone), 1051, 1073 (C-O) | | UV (EtOH) λ max (log ε) | |
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| NP-HPLC | column Silasorb 600 (4 x 250 mm), flow-rate 0.8 ml.min-1, solvent Et2O-CH3CN-H2O (780:190: 30), Ret 42.6 min (20E 31.7 min) | | HPTLC | | | TLC | | | GLC | | | RP-HPLC | column Separon SIX C18 (4 x 250 mm), solvent MeOH-H2O, linear gradient 10 to 70 % MeOH in 50 min, flow-rate 0.6 ml.min-1, Ret 41.1 min (20E 42.7 min). |
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Drosophila melanogaster BII cell assay: EC50 = 3.0 x 10-6M |
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Permanent link to this datasheet: ATROTOSTERONE C
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