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Year of first isolation: |
1970 |
| Formula: | C27H46O5 |
| Molecular weight: | 450 |
| Occurence in plants: |
Cheilanthes tenuifolia [Pteridaceae] »  ![Wikipedia: Cheilanthes tenuifolia [Pteridaceae]](/images/wikipedia.png)
Cheilanthes mysurensis [Pteridaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC(C)CCC(C(C)C1CCC2(C1(CCC3C2CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)CC1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)C)O)O)C)C » 
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)C)O)O)C)C »
C1[C@]2([C@@H](C[C@H]([C@H]1O)O)C(=O)C[C@@H]1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@H](C)[C@@H](CCC(C)C)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,8R,9S,10R,13R,14R,17R)-2,3,14-trihydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 26130-75-6 | | PubChem CID | 101297732 | InChiKey
[ ChemIDPlus: search ] | ZQJLJTBAWSHGIA-XHCKOWILSA-N | | InChI | InChI=1S/C27H46O5/c1-15(2)6-7-21(28)16(3)17-9-11-27(32)19-12-22(29)20-13-23(30)24(31)14-25(20,4)18(19)8-10-26(17,27)5/h15-21,23-24,28,30-32H,6-14H2,1-5H3/t16-,17+,18-,19+,20-,21+,23+,24-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 450(M)+ (2.5), 432 (M -18)+(9.5), 417 (1), 414 (M -2x18)+(7), 399 (1.5), 396 (M -3x18)+(1), 381 (0.5), 350 (M - C22-C27)+(3.5), 332 (M-C22-C27-18)+ (21), 302 (M-C20-C27)+ (25), 101 (5.5), 83 (61), 69 (57), 55 (100). | | HR-MS | |
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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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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-Ha | | | 07-Hb | | | 08-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.85 (s ) | | 19-Me | 1.03 (s ) | | 21-Me | 1.24 (d, 6) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.84 (d, 6) | | 27-Me | 0.84 (d, 6) |
| CDCl3 (2,3,22-triOAc) | | 01-Ha | | | 01-Hb | | | 02-Ha | 5.38 (w1/2 = 8) | | 03-He | ~ 4.9 | | 04-Ha | | | 04-He | | | 05-H | | | 07-Ha | | | 07-Hb | | | 08-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.81 | | 19-Me | ~ 0.95 | | 21-Me | ~ 0.95 | | 22-H | ~ 4.9 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.90 (d, 6) | | 27-Me | 0.90 (d, 6) | | acetates | 2.01, 2.05, 2.10 |
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| M.P. | 225-228 °C(or 230°-235°C) | | [α]D20 | -25.9 ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | 3636 (OH), 1684 (or 1704 ?) (carbonyl) | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | NP-TLC on silica, Rf 0.50 (CHCl3 - 96% EtOH 4:1) (ecdysone 0.20) | | GLC | | | HPLC | |
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Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-7M |
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Permanent link to this datasheet: CHEILANTHONE B
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