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Year of first isolation: |
1968 |
| Formula: | C27H42O6 |
| Molecular weight: | 462 |
| Occurence in plants: |
Blechnum niponicum [Blechnaceae] »  ![Wikipedia: Blechnum niponicum [Blechnaceae]](/images/wikipedia.png)
Stachyurus praecox [Stachyuraceae] »
Vitex canescens [Lamiaceae (alt. Labiatae)] »
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![SHIDASTERONE [= STACHYSTERONE D]](images/ecdy/280.gif)
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| Canonical SMILES | CC1(CCC(O1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)(C5CCC(O5)(C)C)O)O » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-17-[(1R)-1-(5,5-dimethyloxolan-2-yl)-1-hydroxyethyl]-2,3,14-trihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 26361-67-1 | | PubChem CID | 15227299 | InChiKey
[ ChemIDPlus: search ] | JWXMXJQGIRXWDG-SASGHFKCSA-N | | InChI | InChI=1S/C27H42O6/c1-23(2)9-8-22(33-23)26(5,31)21-7-11-27(32)16-12-18(28)17-13-19(29)20(30)14-24(17,3)15(16)6-10-25(21,27)4/h12,15,17,19-22,29-32H,6-11,13-14H2,1-5H3/t15-,17-,19+,20-,21-,22?,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 462 [M]+, 405 (1) 363 (19), 345 (50), 327 (15), 99 (C22-C27; 60), 81 (54), 43 (100). | | FAB-MS m/z | 485 [M+Na]+ (13.7), 463 [M+H]+ (55), 445 (24.2), 123 (100). | | HR-MS | 463.3028 (M+H)+, calculated 463.3059) |
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| C5D5N | | 01 | 37.7 | | 02 | 67.9 | | 03 | 67.9 | | 04 | 32.2 | | 05 | 51.2 | | 06 | 205.5 | | 07 | 121.5 | | 08 | 166.0 | | 09 | 34.2 | | 10 | 38.5 | | 11 | 21.0 | | 12 | 31.5 | | 13 | 47.5 | | 14 | 84.0 | | 15 | 31.5 | | 16 | 21.5 | | 17 | 51.2 | | 18 | 17.8 | | 19 | 24.3 | | 20 | 80.3 | | 21 | 21.0 | | 22 | 84.8 | | 23 | 27.6 | | 24 | 38.8 | | 25 | 75.4 | | 26 | 28.2 | | 27 | 28.7 |
| CD3OD | | 01 | 37.3 | | 02 | 68.6 | | 03 | 68.4 | | 04 | 32.7 | | 05 | 51.7 | | 06 | 206.4 | | 07 | 122.0 | | 08 | 167.9 | | 09 | 35.0 | | 10 | 39.2 | | 11 | 21.6 | | 12 | 32.2 | | 13 | 48.6 | | 14 | 85.2 | | 15 | 31.6 | | 16 | 21.4 | | 17 | 51.7 | | 18 | 18.0 | | 19 | 24.3 | | 20 | 76.9 | | 21 | 20.6 | | 22 | 85.4 | | 23 | 28.4 | | 24 | 39.5 | | 25 | 81.7 | | 26 | 28.3 | | 27 | 28.9 |
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| C5D5N | | 01-Ha | | | 01-Hb | | | 02-Ha | ~ 4.10 (m ) | | 03-He | 4.19 (ddd ) | | 04-Ha | | | 04-He | | | 05-H | 2.95 (dd ) | | 07-H | 6.29 (d ) | | 09-Ha | 3.53 (ddd ) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 1.06 (s ) | | 19-Me | 1.06 (s ) | | 21-Me | 1.39 (s ) | | 22-H | 4.06 (dd ) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.22 (s ) | | 27-Me | 1.22 (s ) |
| CD3OD | | 01-Ha | 1.42 (dd, 13, 12) | | 01-Hb | | | 02-Ha | | | 02-Ha ~ | 3.84 (ddd, 12, 3, 3) | | 03-He | 3.94 (m, w1/2 = 20) | | 04-Ha | | | 04-He | | | 05-H | 2.36 (m, w1/2 = 25) | | 07-H | 5.81 (d, 2.5) | | 09-Ha | 3.15 (ddd, 12, 7.5, 2.5) | | 11-Ha | | | 11-He | | | 12-Ha | 2.15 (ddd, 13, 13, 4) | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.36 (m, w1/2 = 25) | | 18-Me | 0.84 (s ) | | 19-Me | 0.96 (s ) | | 21-Me | 1.21 (s ) | | 22-H | 3.94 (m, w1/2 = 20) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.25 (s ) | | 27-Me | 1.24 (s ) |
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| M.P. | 245-250 °C (decomp.) | | [α]D25 | + 65.0° (c 0.18; CHCl3) | | IR (CHCl3) ν max (cm-1) | 3600 (sharp, free OH), 3400 (broad, bonded OH), 1664 | | UV (EtOH) λ max (log ε) | 243 (4.04) |
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| HPTLC | | | TLC | Rf 0.40 (CHCl3-EtOH 7:1, olive-green spot | | GLC | | | HPLC | RP-HPLC, Column Spherisorb 5ODS2, MeOH-H2O 60:40 (v/v), Ret. 34.0 min |
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Drosophila melanogaster BII cell assay: EC50 = 4.0 x 10-6M | Drosophila melanogaster BII cell assay: EC50 = 1.5 x 10-6M | Chilo dipping test: inactive |
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| First isolation | TAKEMOTO, T. et al. (1968) Tetrahedron Lett. 6095-6098 |
 | | General | TAKEMOTO, T. et al. (1969) Chem. Pharm. Bull. 17, 1973-1974 |
| | First isolation | IMAI, S. et al. (1970) Chem. Commun., 352-353 |
| | General | HIKINO, H. et al. (1975) Tetrahedron 23, 1458-1479 |
| | Bioactivities | BERGAMASCO, R. et al. (1980) In: Progress in Ecdysone Research (Ed. J.A. Hoffmann), Elsevier/North Holland Biomed. Press, Amsterdam 299-324 |
| | General | ROUSSEL, P.G. et al. (1995) J. Chem. Soc., Chem. Commun. 933-934 |
| | General | SUKSAMRARN, A. et al. (1997) Phytochemistry 45, 1149-1152 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
| | 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: SHIDASTERONE [= STACHYSTERONE D]
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