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Year of first isolation: |
1968 |
Formula: | C27H44O6 |
Molecular weight: | 464 |
Occurence in plants: |
Blechnum minus [Blechnaceae] »
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Occurence in animals: |
Jasus lalandii [Crustaceae] » Schistocerca gregaria [Orthoptera] » Zoanthus sp. [Zoanthidae] »
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Canonical SMILES | CC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)O)O)O)C)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)O)O)O)C)C »
| IUPAC Name | (3S,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | CAS-RN | 17942-08-4 | PubChem CID | 9912297 | InChiKey [ ChemIDPlus: search ] | JNTQSSGVHLUIBL-GLPVALQZSA-N | InChI | InChI=1S/C27H44O6/c1-23(2,31)10-9-22(30)26(5,32)21-8-13-27(33)18-15-20(29)19-14-16(28)6-11-24(19,3)17(18)7-12-25(21,27)4/h15-17,19,21-22,28,30-33H,6-14H2,1-5H3/t16-,17-,19-,21-,22+,24+,25+,26+,27+/m0/s1 |
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CI-MS (isobutane) m/z | 465 (M+H)+ (6%); CI-MS (NH3) m/z 465 (M+H)+, 447, 429, 411, 347, 331, 329, 313 | EI-MS m/z (relative intensity %) | 428 (M-2x18)+ (0.5), 397 (2), 347 (M-C22-C27)+ (9), 284 (M-C20-C27-18)+ (6), 99 (17), 81 (34), 43 (100) | HR-MS | |
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C5D5N | 01 | 29.5 (t) | 02 | 27.5 (t) | 03 | 64.12 (d) | 04 | 33.2 (t) | 05 | 51.75 (d) | 06 | 203.18 (s) | 07 | 121.5 (d) | 08 | 166.7 (s) | 09 | 34.3 (d) | 10 | 37.0 (s) | 11 | 21.7 (t) | 12 | 32.31 (t) | 13 | 48.59 (s) | 14 | 84.42 (s) | 15 | 31.63 (t) | 16 | 21.7 (t) | 17 | 50.17 (d) | 18 | 17.9 (q) | 19 | 24.38 (q) | 20 | 76.9 (s) | 21 | 21.57 (q) | 22 | 77.6 (d) | 23 | 29.12 (t) | 24 | 42.63 (t) | 25 | 69.58 (s) | 26 | 30.1 (q)* | 27 | 30.04 (q)* |
CD3OD | 01 | 28.32 | 02 | 25.66 | 03 | 64.04 | 04 | 31.87 | 05 | 50.60 | 06 | 205.6 | 07 | 120.8 | 08 | 167.0 | 09 | 33.5 | 10 | 36.3 | 11 | 20.14 | 12 | 31.2 | 13 | 49.45 | 14 | 84.3 | 15 | 30.45 | 16 | 20.14 | 17 | 48.88 | 18 | 17.0 | 19 | 23.5 | 20 | 76.56 | 21 | 20.06 | 22 | 76.76 | 23 | 27.5 | 24 | 40.66 | 25 | 70.34 | 26 | 28.61 | 27 | 28.61 |
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C5D5N | 01-Ha | | 01-He | | 02-Ha | | 02-He | | 03-He | 4.12 (br, s) | 04-Ha | | 04-He | | 05-H | 2.97 (m) | 07-H | 6.25 (d, 2.1) | 09-Ha | 3.54 (m) | 11-Ha | | 11-He | | 12-Ha | | 12-He | | 15-Ha | | 15-Hb | | 16-Ha | | 16-Hb | | 17-H | 3.03 (t, 9) | 18-Me | 1.23 (s ) | 19-Me | 1.05 (s ) | 21-Me | 1.60 (s ) | 22-H | 3.88 (br, d, 10.3) | 23-Ha | | 23-Hb | | 24-Ha | | 24-Hb | | 26-Me | 1.36 (s ) | 27-Me | 1.36 (s ) |
CD3OD | 01-Ha | | 01-He | | 02-Ha | | 02-He | | 03-He | 3.96 (m, w1/2=12) | 04-Ha | | 04-He | | 05-H | 2.38 (dd, 12, 5) | 07-H | 5.80 (d, 2.5) | 09-Ha | 3.20 (m, w1/2=22) | 11-Ha | | 11-He | | 12-Ha | 2.13 (ddd, 13, 13, 5) | 12-He | | 15-Ha | | 15-Hb | | 16-Ha | | 16-Hb | | 17-H | 2.39 (m ) | 18-Me | 0.89 (s ) | 19-Me | 0.96 (s ) | 21-Me | 1.19 (s ) | 22-H | 3.33 (dd, 11, 2) | 23-Ha | | 23-Hb | | 24-Ha | | 24-Hb | | 26-Me | 1.19 (s ) | 27-Me | 1.20 (s ) |
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M.P. | 250-252 °C ; | [α]D20 | | IR (KBr) ν max (cm-1) | 3450 (OH), 1645 (cyclohexenone); | UV (EtOH) λ max (log ε) | 243 (4.083) ; |
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TLC | NP-TLC : Rf 0.51 (silica plates, solvent CHCl3-MeOH 4:1 v/v) (E : 0.39); Rf 0.15 (silica plates, solvent CHCl3-96%EtOH 4:1 v/v) (E : 0.21); RP-TLC : Rf 0.28 (C18-bonded silica gel, solvent MeOH-H2O 65:35) (E : 0.35) | GLC | as TMS ethers on 1.5% OV101, 285°C, derivat. 5h at 120°C, Ret 8.5 min (E : 6.5 min) | HPLC | NP-HPLC, Retention time 9.4 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 17.2 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) RP-HPLC, Retention time 12.9 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent CH3CN- 0.1% TFA in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.5 min) |
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Drosophila melanogaster BII cell assay: EC50 = 6.6 x 10-7M | Drosophila melanogaster BII cell assay: EC50 = 1.3 x 10-6M | Drosophila melanogaster Kc-H cell assay: EC50 = 4.7 x 10-7M | Galleria mellonella in vivo assay: ED50 = 12.5 ug/g | Sarcophaga bullata in vivo assay: ED50 = 26.0 ug/g | Calliphora assay: 100% (20-hydroxyecdysone = 100%) |
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First isolation | GALBRAITH, M.N. et al. (1968) J. Chem. Soc., Chem. Commun. 83-85 |
| General | CHONG, Y.K. et al. (1970) J. Chem. Soc., Chem. Commun. 1217-1218 |
| Bioactivities | CHERBAS, L. et al. (1980) W. Roux Arch. Devel. Biol. 189, 1-15 |
| Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| General | ISAAC, R.E. et al. (1981) J. Chem. Soc., Chem. Commun. 418-420 |
| General | WILSON, I.D. et al. (1985) J. Chromatogr. 318, 373-377 |
| General | BIELBY, C.R. et al. (1986) J. Chromatogr. 351, 57-64 |
| General | KAMETANI, T. et al. (1986) J. Org. Chem. 51, 2932-2939 |
| Bioactivities | SLÁMA, K. et al. (1993) Insect Biochem. Molec. Biol. 23, 181-185 |
| General | SUKSAMRARN, A. et al. (1996) Tetrahedron 52, 12623-12630 |
| Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
| General | PARAMESWARAN, P.S. et al. (2001) J. Indian Inst. Sci. 81, 169-173 |
| Bioactivities | DINAN, L. et al. (2003) In: Studies in Natural Products Chemisty (ed. Atta-ur-Rahman), Elsevier, Amsterdam, 29, 3-71 |
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Permanent link to this datasheet: 2-DEOXY-20-HYDROXYECDYSONE
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