|
|
|
|
Year of first isolation: |
1995 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Rhaponticum carthamoides [Asteraceae] »  ![Wikipedia: Rhaponticum carthamoides [Asteraceae]](/images/wikipedia.png)
|
| Occurence in animals: |
|
|
|
| |
| Canonical SMILES | CC12CCC3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](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](O)CCC(C)(C)O)O)O)C)O)C » 
| | IUPAC Name | (2R,3S,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 40884438 | InChiKey
[ ChemIDPlus: search ] | GMFLGNRCCFYOKL-RMHPOYOUSA-N | | InChI | InChI=1S/C27H44O8/c1-22(2,32)9-8-20(30)25(5,33)19-7-11-26(34)16-12-21(31)27(35)14-18(29)17(28)13-24(27,4)15(16)6-10-23(19,26)3/h12,15,17-20,28-30,32-35H,6-11,13-14H2,1-5H3/t15-,17+,18-,19-,20+,23+,24+,25+,26+,27+/m0/s1 |
| |
| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 478 (M-18)+, 463, 445, 427, 409, 391, 379 (M-117)+, 361, 325, 301, 99, 81 | | HR-MS | |
|
|
| C5D5N | | 01 | 36.0 | | 02 | 69.8 | | 03 | 67.9 | | 04 | 34.8 | | 05 | 79.8 | | 06 | 200.9 | | 07 | 119.8 | | 08 | 166.8 | | 09 | 38.2 | | 10 | 44.7 | | 11 | 21.3 | | 12 | 31.6 | | 13 | 48.1 | | 14 | 84.0 | | 15 | 32.0 | | 16 | 22.0 | | 17 | 50.0 | | 18 | 17.1 | | 19 | 17.8 | | 20 | 76.8 | | 21 | 21.6 | | 22 | 77.5 | | 23 | 27.4 | | 24 | 42.6 | | 25 | 69.6 | | 26 | 29.9 | | 27 | 30.1 |
|
| C5D5N | | 01-Ha | | | 01-He | | | 02-He | 4.14 (k, w1/2= 8.5) | | 03-Ha | 4.25 (dt, w1/2 = 22)) | | 04-Ha | 2.08* | | 04-He | 2.15* | | 07-H | 6.24 (br s ) | | 09-H | 3.61 (m ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.95 (t ) | | 18-Me | 1.12 (s ) | | 19-Me | 1.18 (s ) | | 21-Me | 1.56 (s ) | | 22-H | 3.83 (dd ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.35 (s ) | | 27-Me | 1.35 (s ) |
|
| |
| M.P. | 246-248 °C | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3370-3490 (OH), 1690 (cyclohexenone) | | UV (EtOH) λ max (log ε) | |
| |
| HPTLC | | | TLC | | | GLC | | | HPLC | | | LC | Silica column eluted with CHCl3-MeOH (20:1). |
| |
Drosophila melanogaster BII cell assay: EC50 = 1.0 x 10-9M | Galleria mellonella in vivo assay: ED50 = 7.8 ug/g | Sarcophaga bullata in vivo assay: ED50 = 7.8 ug/g |
| |
| |
Permanent link to this datasheet: RAPISTERONE D
|
|
