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Year of first isolation: |
1996 |
| Formula: | C24H32O6 |
| Molecular weight: | 416 |
| Occurence in plants: |
Silene dioica [Caryophyllaceae] »  ![Wikipedia: Silene dioica [Caryophyllaceae]](/images/wikipedia.png)
Silene otites [Caryophyllaceae] »
Briza maxima [Poaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1(CCC2C5(C=CC(=O)O5)C)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]2C1(C)OC(=O)C=C1)O)C)C » 
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@@]1(C)OC(=O)C=C1)O)C)C »
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@]1(C)OC(=O)C=C1)O)C)C »
| | IUPAC Name | (5S)-5-methyl-5-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]furan-2-one | | CAS-RN | 176391-32-5 | | PubChem CID | 56601999 | InChiKey
[ ChemIDPlus: search ] | NWSCKDFQLPIHHX-PCSJRHQKSA-N | | InChI | InChI=1S/C24H32O6/c1-21-12-18(27)17(26)11-15(21)16(25)10-14-13(21)4-7-22(2)19(5-9-24(14,22)29)23(3)8-6-20(28)30-23/h6,8,10,13,15,17-19,26-27,29H,4-5,7,9,11-12H2,1-3H3/t13-,15-,17+,18-,19-,21+,22+,23-,24+/m0/s1 |
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| CI-MS (NH3) m/z | 434 (M+H+NH3)+, 417 (M+H)+, 399 (MH - 18)+ | | HR-MS | HR-EIMS: 416.21978 (M)+ C24H32O6 requires 416.21988 |
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| CD3OD | | 01 | 37.38 | | 02 | 68.70 | | 03 | 68.49 | | 04 | 32.85 | | 05 | 51.80 | | 06 | 206.20 | | 07 | 122.32 | | 08 | 167.10 | | 09 | 35.07 | | 10 | 39.20 | | 11 | 21.46 | | 12 | 31.92 | | 13 | 48.30 | | 14 | 85.00 | | 15 | 31.56 | | 16 | 22.56 | | 17 | 52.20 | | 18 | 18.16 | | 19 | 24.37 | | 20 | 92.80 | | 21 | 25.17 | | 22 | 163.92 | | 23 | 120.05 | | 24 | 175.50 |
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| CD3OD | | 01-Ha | 1.43 (t, 12) | | 01-He | 1.78 | | 02-Ha | 3.82 (ddd, 12, 3.5, 3) | | 03-He | 3.94 (q, b, w1/2 = 9) | | 04-Ha | 1.65 | | 04-He | 1.75 | | 05-H | 2.38 (dd, 11.3, 5.4) | | 07-H | 5.78 (d, 2.5) | | 09-Ha | 3.14 (m, w1/2 = 22) | | 11-Ha | 1.65 | | 11-He | 1.8 | | 12-Ha | 2.19 (dt, 13, 5) | | 12-He | 1.85 | | 15-Ha | 1.95 | | 15-Hb | 1.65 | | 16-Ha | 1.8 | | 16-Hb | 1.45 | | 17-H | 2.77 (t, 9.2) | | 18-Me | 0.76 (s ) | | 19-Me | 0.95 (s ) | | 21-Me | 1.52 (s ) | | 22-H | 7.76 (d, 5.4) | | 23-H | 6.01 (d, 5.4) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 1749 (CO of an ethylenic ?-lactone), 1643 (cyclohexenone). | | UV (EtOH) λ max (log ε) | 240 (4.12) |
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| HPTLC | | | TLC | | | GLC | ) | | HPLC | NP-HPLC : Zorbax-Sil (250 mm long, 9.4 mm i.d.) Ret 14.0 min (solvent CH2Cl2-iPrOH-H2O 125:25:2, flow-rate 4 ml.min-1); Ret 26.0 min (solvent cyclohexane-iPrOH-H2O 100:40:3) |
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Drosophila melanogaster BII cell assay: EC50 = 4.3 x 10-6M |
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| First isolation | GIRAULT, J.-P. et al. (1996) J. Nat. Prod. 59, 522-524 |
 | | General | SAVCHENKO, T. et al. (1998) Biochem. Syst. Ecol. 26, 781-791 |
| | Bioactivities | DINAN, L. et al. (2005) In: Comprehensive Molecular Insect Science (eds. L. I. Gilbert, C. Iatrou, S. Gill), Elsevier, Oxford, III, 197-242 |
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Permanent link to this datasheet: SIDISTERONE
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