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Year of first isolation: |
1997 |
| Formula: | C33H54O12 |
| Molecular weight: | 642 |
| Occurence in plants: |
Xerophyllum tenax [Melanthiaceae] »  ![Wikipedia: Xerophyllum tenax [Melanthiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)OC5C(C(C(C(O5)CO)O)O)O)C)C1(CCC2C(C)(C(CCC(C)(C)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)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 | (2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-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 | | | PubChem CID | 102210228 | InChiKey
[ ChemIDPlus: search ] | KUHPYTJXVKKPHR-RVRQMSSNSA-N | | InChI | InChI=1S/C33H54O12/c1-29(2,41)9-8-24(37)32(5,42)23-7-11-33(43)17-12-19(35)18-13-20(36)21(14-30(18,3)16(17)6-10-31(23,33)4)44-28-27(40)26(39)25(38)22(15-34)45-28/h12,16,18,20-28,34,36-43H,6-11,13-15H2,1-5H3/t16-,18-,20+,21-,22+,23-,24+,25+,26-,27+,28+,30+,31+,32+,33+/m0/s1 |
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| CI-MS (NH3) m/z | | | EI-MS m/z (relative intensity %) | 463 [M-C6H11O6], 462, 446, 444, 443, 428, 427, 426, 408, 376, 368, 346, 345, 344, 330, 329, 328, 327, 326, 302, 301, 300, 285, 284, 267, 266, 189, 188, 179 [C6H11O6], 178, 177, 163, 159, 113, 99, 69, 55. | | FAB-MS (negative mode, in glycerol) | 641 [M-H] ? |
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| C5D5N | | 01 | 35.9 | | 02 | 75.8 | | 03 | 64.6 | | 04 | 31.3 | | 05 | 51.3 | | 06 | 202.9 | | 07 | 121.7 | | 08 | 133.0 | | 09 | 34.4 | | 10 | 38.6 | | 11 | 20.9 | | 12 | 31.9 | | 13 | 48.0 | | 14 | 84.1 | | 15 | 31.6 | | 16 | 21.4 | | 17 | 50.0 | | 18 | 17.8 | | 19 | 24.2 | | 20 | 76.8 | | 21 | 21.6 | | 22 | 77.5 | | 23 | 27.6 | | 24 | 42.6 | | 25 | 69.5 | | 26 | 30.0 | | 27 | 30.1 | | glu-1' | 101.7 | | glu-2' | 75.4 | | glu-3' | 78.7 | | glu-4' | 71.6 | | glu-5' | 78.6 | | glu-6' | 62.7 |
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| C5D5N | | 01-Ha | 1.94 | | 01-He | 2.16 | | 02-Ha | 4.29 (M) | | 03-He | 4.36 (m) | | 04-Ha | 2.04 | | 04-He | 1.80 | | 05-H | 2.96 | | 07-H | 6.23 (d, 2.3) | | 11-Ha | 1.72 | | 11-He | 1.89 | | 12-Ha | 2.46 (ddd 13, 13, 5) | | 12-He | 1.92 | | 15-Ha | 2.14 | | 15-Hb | 1.90 | | 16-Ha | 2.43 | | 16-Hb | 2.04 | | 17-H | 2.94 | | 18-Me | 1.19 (s) | | 19-Me | 1.03 (s) | | 21-Me | 1.58 (s) | | 22-H | 3.87 (br d, 10) | | 23-Ha | 2.12 | | 23-Hb | 1.85 | | 24-Ha | 2.28 | | 24-Hb | 1.83 | | 26-Me | 1.39 (s) | | 27-Me | 1.39 (s) | | glu-H1' | 5.02 (d, 7.9) | | glu-H2' | 4.05 (t, 8.0) | | glu-H3' | 4.32 | | glu-H4' | 4.25 (t, 9.0) | | glu-H5' | 4.0 (m) | | glu-H6',6" | 4.36, 4.54 (d, 11.8) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 244 (4.09), 320 (3.15) |
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| HPTLC | | | TLC | | | RP-HPLC | column Spherisorb 5ODS2 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with 18% ACN-iPrOH (5:2) in 0.1% TFA in H2O, Ret 10.2 min (20E 13.9 min); column Separon SGX-C18 25 cm long, 8 mm i.d., flow-rate 4 ml.min-1, eluted with 40% MeOH in water, Ret 13.5 min. | | NP-HPLC | NP-HPLC, column Zorbax-SIL 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with cyclohexane-iPrOH-H2O (125:50:5), Ret 50.4 min (20E 10.1 min), NP-HPLC, column Zorbax-SIL 25 cm long, 4.6 mm i.d., flow-rate 1 ml.min-1, eluted with cyclohexane-iPrOH-H2O (80:40:3), Ret 31.1 min (20E 12.3 min). |
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Drosophila melanogaster BII cell assay: EC50 = 2.0 x 10-5M |
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| General | PIS, J. et al. (1994) Tetrahedron 50, 9679-9690 |
 | | General | PIS, J. et al. (1995) Eur. J. Entomol. 92, 41-50 |
| | Bioactivities | HARMATHA, J. et al. (1997) Arch. Insect Biochem. Physiol. 35, 219-225 |
| | First isolation | ALISON, B. et al. (1997) Biochem. Syst. Ecol. 25, 255-261 |
| | General | SARKER, S.D. et al. (1997) Phytochemistry 44, 513-521 |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 2-β-D-GLUCO-PYRANOSIDE
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