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Year of first isolation: |
1966 |
| Formula: | C27H44O4 |
| Molecular weight: | 432 |
| Occurence in plants: |
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| Occurence in animals: |
metabolite formed in insects and crustaceans » 
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| Canonical SMILES | CC(C)CCCC(C)C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)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]2[C@H](C)CCCC(C)C)O)C)C » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 11224256 | InChiKey
[ ChemIDPlus: search ] | QPGHAYOKHPQLQO-DXCOFLLLSA-N | | InChI | InChI=1S/C27H44O4/c1-16(2)7-6-8-17(3)18-10-12-27(31)20-13-22(28)21-14-23(29)24(30)15-25(21,4)19(20)9-11-26(18,27)5/h13,16-19,21,23-24,29-31H,6-12,14-15H2,1-5H3/t17-,18-,19+,21+,23-,24+,25-,26-,27-/m1/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 432 (M)+(5), 414 (100), 404 (10), 399 (16), 396 (7), 381 (18), 302 (9), 301 (22), 249 (5), 213 (5) | | HR-MS | |
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| C5D5N | | 01 | 37.9 | | 02 | 68.0 | | 03 | 68.0 | | 04 | 34.4 | | 05 | 51.3 $ | | 06 | 203.4 | | 07 | 121.5 | | 08 | 166.7 | | 09 | 34.5 | | 10 | 38.6 | | 11 | 20.9 | | 12 | 31.7 * | | 13 | 47.2 | | 14 | 84.2 | | 15 | 31.4 * | | 16 | 27.3 | | 17 | 51.1 $ | | 18 | 15.8 | | 19 | 24.3 | | 20 | 36.0 ** | | 21 | 19.2 | | 22 | 36.7 ** | | 23 | 24.3 L | | 24 | 39.7 | | 25 | 28.1 | | 26 | 22.6 L | | 27 | 22.8 L |
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| C5D5N | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.71 0.75 | | 19-Me | 1.07 1.08 | | 21-Me | 1.00 (d, 6) 1.06-0.975 | | 22-Ha | | | 22-Hb | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 0.85 (d, 6) 0.925-0.83 | | 27-Me | 0.85 (d, 6) 0.925-0.83 |
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| M.P. | 207-209 °C ; | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3540, 3380 (OH), 1656 (C=O), 1612 (C=C); | | UV (EtOH) λ max (log ε) | 242 (4.086) ; |
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Drosophila melanogaster BII cell assay: EC50 = ca. 10-6M | Calliphora assay: 10% (20-hydroxyecdysone = 100%) | Musca assay: 17% (20-hydroxyecdysone = 100%) |
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| First isolation | FURLENMEIER, A. et al. (1966) Helv. Chim. Acta 49, 1591-1601 |
 | | General | HORN, D.H.S. et al. (1971) In: Marcel Dekker Inc., New York, pp. 333-459 |
| | General | KAPLANIS, J.N. et al. (1972) Steroids 20, 105-120 |
| | General | HIKINO, H. et al. (1975) Chem. Pharm. Bull. 23, 125-132 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | MEISTER, M.F. et al. (1985) Mol. Cell. Endocrinol. 41, 27-44 |
| | General | LACHAISE, F. et al. (1986) Mol. Cell. Endocrinol. 45, 253-261 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
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Permanent link to this datasheet: 22,25-DIDEOXYECDYSONE
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