|
|
|
|
Year of first isolation: |
1997 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Vitex canescens [Lamiaceae (alt. Labiatae)] »  ![Wikipedia: Vitex canescens [Lamiaceae (alt. Labiatae)]](/images/wikipedia.png)
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CC(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]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](C[C@H](C(C)(C)O)O)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R,3R,5R)-2,3,5,6-tetrahydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 11103069 | InChiKey
[ ChemIDPlus: search ] | NXKBQUXBPMOHPK-ZHMUISTKSA-N | | InChI | InChI=1S/C27H44O8/c1-23(2,33)21(31)12-22(32)26(5,34)20-7-9-27(35)15-10-17(28)16-11-18(29)19(30)13-24(16,3)14(15)6-8-25(20,27)4/h10,14,16,18-22,29-35H,6-9,11-13H2,1-5H3/t14-,16-,18+,19-,20-,21+,22+,24+,25+,26+,27+/m0/s1 |
| |
| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | | | HR-FAB-MS | 497.3123 [M+H]+, calculated for C27H45O8: 497.3114 |
|
|
| C5D5N | | 01 | 37.9 | | 02 | 68.1a | | 03 | 68.0a | | 04 | 32.3 | | 05 | 51.3 | | 06 | 203.4 | | 07 | 121.6 | | 08 | 166.1 | | 09 | 34.4 | | 10 | 38.6 | | 11 | 21.1 | | 12 | 31.7 | | 13 | 48.1 | | 14 | 84.2 | | 15 | 31.9 | | 16 | 21.3 | | 17 | 50.0 | | 18 | 17.9 | | 19 | 24.4 | | 20 | 76.8 | | 21 | 21.7 | | 22 | 73.7b | | 23 | 35.2 | | 24 | 75.9b | | 25 | 72.6 | | 26 | 26.1 | | 27 | 26.0 |
|
| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | 4.18 (m) | | 03-He | 4.23 (br, s) | | 04-Ha | | | 04-He | | | 05-H | 3.01 (dd, 13.1, 3.6) | | 07-H | 6.26 (d, 2.7) | | 09-H | 3.57 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.08 (t, 9.1) | | 18-Me | 1.22 (s) | | 19-Me | 1.06 (s) | | 21-Me | 1.63 (s) | | 22-H | 4.51 (dd, 9.6, 2.3) a | | 23-Ha | | | 23-Hb | | | 24-H | 4.37 (dd, 9.0, 2.7) a | | 26-Me | 1.46 (s) | | 27-Me | 1.47 (s) |
|
| |
| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3408, 2962, 1651, 1444, 1383, 1303, 1057, 950, 877 | | UV (EtOH) λ max (log ε) | |
| |
| HPTLC | | | TLC | Silica, CHCl3-MeOH 5:1 | | GLC | | | HPLC | Column Spherisorb ODS2 5?m (250x4.6 mm), solvent MeOH-H2O (1:3) |
| |
Drosophila melanogaster BII cell assay: EC50 = 1.2 x 10-6M |
| |
| |
Permanent link to this datasheet: 24-EPI-ABUTASTERONE
|
|
