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Year of first isolation: |
1991 |
| Formula: | C27H44O8 |
| Molecular weight: | 496 |
| Occurence in plants: |
Rhaponticum uniflorum [Asteraceae] »  ![Wikipedia: Rhaponticum uniflorum [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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![RHAPONTISTERONE [= PUNISTERONE]](images/ecdy/277.gif)
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| Canonical SMILES | CC(C)C(CC(C(C)(C1CCC2(C1(CC(C3C2=CC(=O)C4C3(CC(C(C4)O)O)C)O)C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | CC(C)[C@H](C[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(C[C@H]([C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)O)C)O)O)O)O » 
| | IUPAC Name | (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R,5S)-2,3,5-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 137476-71-2 | | PubChem CID | 11799446 | InChiKey
[ ChemIDPlus: search ] | PJHYXCVCRWJEMV-XYFSXPBDSA-N | | InChI | 1S/C27H44O8/c1-13(2)16(28)10-22(33)26(5,34)21-6-7-27(35)15-9-17(29)14-8-18(30)19(31)11-24(14,3)23(15)20(32)12-25(21,27)4/h9,13-14,16,18-23,28,30-35H,6-8,10-12H2,1-5H3/t14-,16-,18+,19-,20+,21-,22+,23+,24-,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 496 (M+H+NH3-H2O)+, 479, 461, 443, 425, 407, 391, 362 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| D2O* | | 01 | 36.9 | | 02 | 66.9 | | 03 | 66.9 | | 04 | 31.4 | | 05 | 51.1 | | 06 | 206.4 | | 07 | 121.5 | | 08 | 164.9 | | 09 | 41.1 | | 10 | 38.2 | | 11 | 68.1 | | 12 | 41.5 | | 13 | 47.1 | | 14 | 84.3 | | 15 | 30.2 | | 16 | 19.9 | | 17 | 48.5 | | 18 | 17.4 | | 19 | 22.9 | | 20 | 77.6 | | 21 | 18.9 | | 22 | 75.2 | | 23 | 34.7 | | 24 | 75.5 | | 25 | 31.2 | | 26 | 15.1 | | 27 | 18.5 |
| C5D5N | | 01 | 39.5 | | 02 | 68.1 | | 03 | 67.9 | | 04 | 32.5 | | 05 | 52.2 | | 06 | 203.6 | | 07 | 121.3 | | 08 | 163.9 | | 09 | 42.5 | | 10 | 39.3 | | 11 | 68.6 | | 12 | 43.8 | | 13 | 47.9 | | 14 | 83.9 | | 15 | 31.7 | | 16 | 21.3 | | 17 | 49.6 | | 18 | 18.7 | | 19 | 24.7 | | 20 | 76.4 | | 21 | 21.3 | | 22 | 77.4 | | 23 | 35.4 | | 24 | 76.6 | | 25 | 33.8 | | 26 | 16.9 | | 27 | 19.4 |
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| D2O | | 01-Ha | 1.39 (t, 13) | | 01-He | 2.48 (dd, 13, 3.5) | | 02-Ha | 4.09 (m, w1/2 = 12) | | 03-He | 4.09 (m, w1/2 = 12) | | 04-Ha | 1.75* | | 04-He | 1.75* | | 05-H | 2.32 | | 07-H | 5.98 (d, 2) | | 09-Ha | 3.12 (dd, 9, 2) | | 11-Ha | 4.22 (m, w1/2 = 24) | | 12-Ha | 2.05* | | 12-He | 2.72 (dd, 12, 5.6) | | 15-Ha | 2.06* | | 15-Hb | 1.66* | | 16-Ha | 1.9* | | 16-Hb | 1.8* | | 17-H | 2.3 | | 18-Me | 0.86 (s) | | 19-Me | 1.09 (s) | | 21-Me | 1.27 (s) | | 22-H | 3.61 (d, 10) | | 23-Ha | 1.47 (ddd, 13, 10, 7) | | 23-Hb | 1.8* | | 24-Ha | 3.71 (m, w1/2 = 12) | | 25-H | 1.78 | | 26-Me | 0.89 (d, 6.8) | | 27-Me | 0.96 (d, 6.8) |
| C5D5N | | 01-Ha | 2.25 * | | 01-He | 2.5 * | | 02-Ha | 4.15 (m ) | | 03-He | 4.21 (m ) | | 04-Ha | 2.05 * | | 04-He | 1.8 * | | 05-H | 3.05* | | 07-H | 6.32 (d, 2.5) | | 09-Ha | 3.87 (dd, 8.7,2.5) | | 11-Ha | 4.59 (m, w1/2=26) | | 12-Ha | 3.05 * | | 12-He | 2.27 (dd, 12, 5.6) | | 15-Ha | 2.5 * | | 15-Hb | 1.95 * | | 16-Ha | 1.9 * | | 16-Hb | 2.2* | | 17-H | 3.05* | | 18-Me | 1.33 (s ) | | 19-Me | 1.27 (s ) | | 21-Me | 1.59 (s ) | | 22-H | 4.13 (db, 10) | | 23-Ha | 1.80* | | 23-Hb | 2.00 * | | 24-Ha | 3.94 (m, w1/2=22) | | 25-H | 1.70 * | | 26-Me | 1.003 (d, 6.8) | | 27-Me | 1.006 (d, 6.8) |
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| M.P. | 234-236 °C (decomp) | | [α]D20 | | | IR (KBr) ν max (cm-1) | 1650, 997, 952, 909 | | UV (EtOH) λ max (log ε) | 241.4 (4.08) |
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| HPTLC | | | TLC | | | GLC | | | HPLC | RP-HPLC, column Spherisorb-5ODS2 (250x4.6 mm), flow-rate 1 ml.min-1, eluted with a gradient 30 to 100% MeOH over 30 min, ret 15.6 min (20E 16.4 min) |
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Drosophila melanogaster BII cell assay: EC50 = 8.3 x 10-7M |
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Permanent link to this datasheet: RHAPONTISTERONE [= PUNISTERONE]
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