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Year of first isolation: |
1987 |
| Formula: | C29H46O7 |
| Molecular weight: | 506 |
| Occurence in plants: |
Silene otites [Caryophyllaceae] »  ![Wikipedia: Silene otites [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(=O)OC(CCC(C)(C)O)C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)O)C)C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)OC(=O)C)O)O)C)C » 
| | IUPAC Name | [(2R,3R)-2-[(3S,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2,6-dihydroxy-6-methylheptan-3-yl] acetate | | CAS-RN | | | PubChem CID | 70684795 | InChiKey
[ ChemIDPlus: search ] | SEDXWBHJLQPYQW-OHTZXPRASA-N | | InChI | InChI=1S/C29H46O7/c1-17(30)36-24(10-11-25(2,3)33)28(6,34)23-9-14-29(35)20-16-22(32)21-15-18(31)7-12-26(21,4)19(20)8-13-27(23,29)5/h16,18-19,21,23-24,31,33-35H,7-15H2,1-6H3/t18-,19-,21-,23-,24+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 507 (M+H)+,489, 473, 471 (M+H - 2x18)+, 447, 429, 413, 411, 347, 329. | | EI-MS m/z (relative intensity %) | | | FAB-HR-MS | 507.3320 [M+H]+ (C29H47O7 requires 507.3321) |
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| C5D5N | | 01 | | | 02 | | | 03 | | | 04 | | | 05 | | | 06 | | | 07 | | | 08 | | | 09 | | | 10 | | | 11 | | | 12 | | | 13 | | | 14 | | | 15 | | | 16 | | | 17 | | | 18 | | | 19 | | | 20 | | | 21 | | | 22 | | | 23 | | | 24 | | | 25 | | | 26 | | | 27 | |
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| CD3OD | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 02-He | | | 03-He | 3.98 (m, w1/2=12) | | 04-Ha | | | 04-He | | | 05-H | 2.38 (dd, 12, 4) | | 07-H | 5.81 (d, 2.5) | | 09-Ha | 3.20 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.39 (m ) | | 18-Me | 0.87 (s ) | | 19-Me | 0.95 (s ) | | 21-Me | 1.28 (s ) | | 22-H | 4.87 (d ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.15 (s ) | | 27-Me | 1.16 (s ) | | O-Ac | 2.08 (s ) |
| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | | | 02-He | | | 03-He | 4.12 (br, s) | | 04-Ha | | | 04-He | | | 05-H | 2.98 (m) | | 07-H | 6.24 (d, 1.8) | | 09-Ha | 3.53 (m) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.01 (t, 8.8) | | 18-Me | 1.18 (s ) | | 19-Me | 1.04 (s ) | | 21-Me | 1.63 (s ) | | 22-H | 5.50 (dd, 10.6, 2.1) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.33 (s ) | | 27-Me | 1.34 (s ) | | O-Ac | 2.02 (s ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3414, 2964, 1715, 1651, 1378, 1249, 1043, 949 | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | Rf 0.40 (EtOAc-MeOH-NH4OH, 85:10:5) (20E 0.18); Rf 0.51 (CH2Cl2-EtOH, 85:15) (20E 0.15) | | GLC | | | HPLC | NP-HPLC, Retention time 6.4 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O (125:40:3 v/v/v), flow-rate 1 ml.min-1] (20E : 16.8 min); Retention time 10.1 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O (125:25:2 v/v/v), flow-rate 1 ml.min-1] (20E 37.4 min) |
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Drosophila melanogaster BII cell assay: EC50 = 2.4 x 10-5M |
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| First isolation | LAFONT, R. et al. (1987) In: Insects-Plants (eds., Labeyrie, V., Fabres, G., Lachaise, D.), Dr W. Junk Publishers, Dordrecht, Netherlands, p. 400 |
 | | General | BATHORI, M. et al. (1988) Chromatographia 25, 627-630 |
| | General | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
| | General | SUKSAMRARN, A. et al. (1996) Tetrahedron 52, 12623-12630 |
| | Bioactivities | RAVI, M. et al. (2001) J. Chem. Inf. Comput. Sci. 41, 1587-1604 |
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Permanent link to this datasheet: 2-DEOXY-20-HYDROXYECDYSONE 22-ACETATE
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