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Year of first isolation: |
2002 |
| Formula: | C29H46O8 |
| Molecular weight: | 522 |
| Occurence in plants: |
Leuzea carthamoides [Asteraceae] »  ![Wikipedia: Leuzea carthamoides [Asteraceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C(C)(C(CC(=CCO)C(C)(C)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(=C/CO)/C(C)(C)O)O)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-[(Z,2R,3R)-2,3,7-trihydroxy-5-(2-hydroxypropan-2-yl)hept-5-en-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 15908338 | InChiKey
[ ChemIDPlus: search ] | OYWZANJFAABISX-MOPAPZMWSA-N | | InChI | InChI=1S/C29H46O8/c1-25(2,35)16(8-11-30)12-24(34)28(5,36)23-7-10-29(37)18-13-20(31)19-14-21(32)22(33)15-26(19,3)17(18)6-9-27(23,29)4/h8,13,17,19,21-24,30,32-37H,6-7,9-12,14-15H2,1-5H3/b16-8-/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1 |
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| FAB-MS m/z (relative intensity %) | 545 (20) [M+Na]+, 523 (26) [M+H]+, 505 (20), 487 (17), 480 (34), 469 (15), 465 (21), 451 (9), 433 (15), 417 (13), 405 (12), 392 (20), 387 (17), 373 (31), 365 (15), 363 (13), 351 (55), 350 (58), 341 (100), 334 (51), 327 (50), 319 (20) | | HR-MS | 523.31771 [M+H]+, required 523.32709 for C29H47O8 | | CI-MS (NH3) m/z | |
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| CD3OD (50°C) | | 01 | 37.54 | | 02 | 68.78 | | 03 | 68.60 | | 04 | 32.84 | | 05 | 51.85 | | 06 | 206.40 | | 07 | 122.20 | | 08 | 167.83 | | 09 | 35.24 | | 10 | 39.31 | | 11 | 21.61 | | 12 | 32.56 | | 13 | ~ 49.0* | | 14 | 85.33 | | 15 | 31.81 | | 16 | 21.61 | | 17 | 50.57 | | 18 | 18.01 | | 19 | 24.38 | | 20 | 77.86 | | 21 | 21.00 | | 22 | 78.20 | | 23 | 38.01 | | 24 | 147.18 | | 25 | 73.94 | | 26 | 30.24 | | 27 | 30.94 | | 28 | 128.78 | | 29 | 60.46 |
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| CD3OD (50°C) | | 01-Ha | 1.80 (dd) | | 01-He | 1.43 (dd) | | 02-Ha | 3.84 (ddd) | | 03-He | 3.95 (bq) | | 04-Ha | ~ 1.73 | | 04-He | ~ 1.73 | | 05-H | 2.39 (dd) | | 07-H | 5.81 (d) | | 09-H | 3.16 (ddd) | | 11-Ha | ~ 1.82 | | 11-He | ~ 1.70 | | 12-Ha | 2.15 (dt) | | 12-He | 1.88 | | 15-Ha | 1.96 | | 15-Hb | 1.61 | | 16-Ha | 1.83 | | 16-Hb | 2.02 | | 17-H | 2.42 (dd) | | 18-Me | 0.90 (s) | | 19-Me | 0.97 (s) | | 21-Me | 1.22 (s) | | 22-H | 3.55 (dd) | | 23-Ha | 2.31 | | 23-Hb | 2.16 | | 26-Me | 1.42 (s) | | 27-Me | 1.36 (s) | | 28-H | 5.43 (bt) | | 29-H | 4.31 (dd), 4.28 (dd) |
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| M.P. | - °C ; | | [α]D20 | ? ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | 3405, 1653 | | UV (EtOH) λ max (log ε) | - (-) ; |
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| HPLC | RP-HPLC, Column Separon SGX C-18 (250x4 mm) eluted with a linear gradient 10 to 70% of MeOH in H2O over 50 min, flow-rate 0.6 mL.min-1, Ret 33.6 min (20E 34.2 min) | | NP-HPLC | Column Silasorb 600 (250x4 mm) eluted with (1) n-hexane-EtOH-H2O (812:180:8), flow-rate 0.8 mL.min-1, Ret. 74.6 min (20E 50.7 min), or (2) Et2O-MeCN-H2O (880:102:18), flow-rate 0.8 mL.min-1, Ret. 129.4 min (20E 75.4 min) | | TLC | |
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Drosophila melanogaster BII cell assay: EC50 = 2.2 x 10-8M |
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Permanent link to this datasheet: 24(241)-DEHYDRO-242-HYDROXYMAKISTERONE C
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