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Year of first isolation: |
1988 |
| Formula: | C27H44O5 |
| Molecular weight: | 448 |
| Occurence in plants: |
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| Occurence in animals: |
Mus musculus [Muridae] »  ![Wikipedia: Mus musculus [Muridae]](/images/wikipedia.png)
Gryllus bimaculatus [Orthoptera] »
metabolite of exogenous ecdysone »
Locusta migratoria [Orthoptera] »
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| Canonical SMILES | | 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(C1CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)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@H]1CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)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@@H]1CC[C@@H]2[C@H](C)[C@@H](CCC(C)(C)O)O)C)C »
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,17R)-17-((2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl)-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,9,10,11,12,13,14,15,16,17-tetradecahydro-6H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | GWHYLAWOMCRKRC-GVGVEOICSA-N | | InChI | InChI=1S/C27H44O5/c1-15(21(28)9-10-25(2,3)32)17-6-7-18-16-12-22(29)20-13-23(30)24(31)14-27(20,5)19(16)8-11-26(17,18)4/h12,15,17-21,23-24,28,30-32H,6-11,13-14H2,1-5H3/t15-,17+,18-,19-,20-,21+,23+,24-,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 466 (M+H+NH3)+, 449, 431, 413, 333, 315, 279 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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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 | 1.43 | | 01-He | 1.78 | | 02-Ha | 3.84 (m, w1/2=22) | | 03-He | 3.94 (m, w1/2=8) | | 04-Ha | 1.65 | | 04-He | 1.75 | | 05-H | 2.38 (dd, 13,4) | | 07-H | 5.63 (t, ~2) | | 09-Ha | 2.69 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | 1.55 | | 12-He | 2.22 | | 14-H | 2.2 (m ) | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 1.48 | | 18-Me | 0.68 (s ) | | 19-Me | 0.97 (s ) | | 21-Me | 0.99 (d, 6.5) | | 22-H | 3.58 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.19 (s ) | | 27-Me | 1.20 (s ) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | NP-HPLC [ Zorbax-Sil 250 mm x 4.6 mm i.d., flow-rate 1 ml.min-1] 1-Ret 9.6 min [solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v] (E : 26 min); 2-Ret 11.6 min [solvent CH2Cl2-iPrOH-H2O 125:20:1.5 v/v/v] (E : 33.8 min); 3-Ret24.4 min [solvent isoC8-iPrOH-H2O 100:30:2 v/v/v] (E 31.2 min)RP-HPLC [Zorbax-ODS 250 mm x 4.6 mm i.d., solvent linear gradient 18% to 40% (in 30 min) of ACN in 0.1% TFA in H2O, flow-rate 1 ml. min-1] Ret 21.2 min (E : 14.8 min) |
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Calliphora assay: 7% (20-hydroxyecdysone = 100%) |
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| General | KERB, U. et al. (1966) Helv. Chim. Acta 49, 1601-1606 |
 | | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | HAAG, T. et al. (1987) Insect Biochem. 17, 291-301 |
| | First isolation | GIRAULT, J.-P. et al. (1988) Drug Metab. Dispos. 16, 716-720 |
| | General | THIRY, E. et al. (1988) Dissertation thesis, University of Ulm, |
| | General | LAFONT, R. et al. (1988) Biochem. Pharmacol. 37, 1174-1177 |
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Permanent link to this datasheet: 14-DEOXYECDYSONE
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