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Year of first isolation: |
1984 |
| Formula: | C29H46O8 |
| Molecular weight: | 522 |
| Occurence in plants: |
Lychnis flos-culculi [Caryophyllaceae] »  ![Wikipedia: Lychnis flos-culculi [Caryophyllaceae]](/images/wikipedia.png)
Ajuga reptans var. atropurpurea [Lamiaceae (alt. Labiatae)] »
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| Occurence in animals: |
Locusta migratoria [Orthoptera] »
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| Canonical SMILES | CC(=O)OC1CC2C(=O)C=C3C(C2(CC1O)C)CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)O)O)O)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)OC(=O)C)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)-2,14-dihydroxy-10,13-dimethyl-6-oxo-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-3-yl] acetate | | CAS-RN | | | PubChem CID | 10951463 | InChiKey
[ ChemIDPlus: search ] | UWFCFVQTAHITKV-OQQOFWQASA-N | | InChI | InChI=1S/C29H46O8/c1-16(30)37-22-14-19-20(31)13-18-17(26(19,4)15-21(22)32)7-11-27(5)23(8-12-29(18,27)36)28(6,35)24(33)9-10-25(2,3)34/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21-,22+,23-,24+,26+,27+,28+,29+/m0/s1 |
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| CI-MS (NH3) m/z | 540, 523 (MH)+, 505, 487, 469, 405 (MH - C22 -C27)+, 387, 345, 329 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| C5D5N | | 01 | 38.64 | | 02 | 66.06 | | 03 | 71.20 | | 04 | 29.62 | | 05 | 51.88 | | 06 | 202.24 | | 07 | 121.55 | | 08 | 166.48 | | 09 | 34.25 | | 10 | 38.48 | | 11 | 21.05 | | 12 | 31.85 | | 13 | 47.99 | | 14 | 84.06 | | 15 | 31.65 | | 16 | 21.38 | | 17 | 50.00 | | 18 | 17.81 | | 19 | 24.21 | | 20 | 76.77 | | 21 | 21.63 | | 22 | 77.48 | | 23 | 27.39 | | 24 | 42.56 | | 25 | 69.49 | | 26 | 29.88 | | 27 | 30.06 |
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| CDCl3 | | 01-Ha | 1.3 | | 01-He | 1.9 | | 02-Ha | 4.02 (m, w1/2=22) | | 03-He | 5.21 (m, w1/2=8) | | 04-Ha | 1.6 | | 04-He | 1.85 | | 05-H | 2.3 | | 07-H | 5.85 (d, 2.5) | | 09-Ha | 3.01 (m, w1/2=22) | | 11-Ha | 1.70 | | 11-He | 1.80 | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | 2.0 | | 16-Hb | 1.75 | | 17-H | 2.33 (m ) | | 18-Me | 0.87 (s ) | | 19-Me | 1.01 (s ) | | 21-Me | 1.21 (s ) | | 22-H | 3.44 (d, 10) | | 23-Ha | 1.35 | | 23-Hb | 1.65 | | 24-Ha | | | 24-Hb | | | 26-Me | 1.24 (s ) | | 27-Me | 1.25 (s ) | | O-Ac | 2.12 (s) |
| C5D5N | | 01-Ha | 1.81* | | 01-He | 2.25* | | 02-Ha | 4.30 (w1/2=22) | | 03-He | 5.51 (w1/2=8) | | 04-Ha | 1.80$ | | 04-He | 1.97$ | | 05-H | 2.67 | | 07-H | 6.24 | | 09-Ha | 3.57 | | 11-Ha | | | 11-He | | | 12-Ha | 2.57 | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 3.00 ( t, w1/2=23) | | 18-Me | 1.23 | | 19-Me | 1.08 | | 21-Me | 1.60 | | 22-H | 3.88 (w1/2=14.7) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.37 | | 27-Me | 1.37 | | O-Ac | 1.98 |
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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 | NP-TLC on silica gel, Rf 0.35 (CHCl3-EtOH 4:1). | | GLC | | | HPLC | 1- Retention time 8.7 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)2-Retention time 13.8 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)3-Retention time 10.8 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN- 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 = 4.7 x 10-7M |
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| General | GALBRAITH, M.N. et al. (1969) Aust. J. Chem. 22, 1045-1046 |
 | | First isolation | MODDE, J.-F. et al. (1984) Int. J. Invertebr. Reprod. Develop. 7, 161-183 |
| | General | GIRAULT, J.-P. et al. (1990) J. Nat. Prod. 53, 279-293 |
| | General | CALGANO, M.P. et al. (1995) Eur. J. Entomol. 92, 287-294 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 3-ACETATE
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