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Year of first isolation: |
1988 |
| Formula: | C27H44O6 |
| Molecular weight: | 464 |
| Occurence in plants: |
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| Occurence in animals: |
Gryllus bimaculatus [Orthoptera] »  ![Wikipedia: Gryllus bimaculatus [Orthoptera]](/images/wikipedia.png)
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4C3(CC(C(C4)O)O)C)C1CCC2C(C)(C(CCC(C)(C)O)O)O | 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@](C)([C@@H](CCC(C)(C)O)O)O)C)C » 
C[C@]12CC[C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@H]1CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O »
C[C@]12CC[C@H]3C(=CC(=O)[C@@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@H]1CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O »
| | IUPAC Name | (2S,3R,5R,9R,10R,13S,14R,17S)-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one (2S,3R,5S,9R,10R,13S,14S,17S)-2,3-dihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 11213440 11271239 | InChiKey
[ ChemIDPlus: search ] | KBDUJCBPMFPAJU-JGXAIIDDSA-N
KBDUJCBPMFPAJU-RWRGXFHWSA-N | | InChI | InChI=1S/C27H44O6/c1-24(2,32)10-9-23(31)27(5,33)22-7-6-16-15-12-19(28)18-13-20(29)21(30)14-26(18,4)17(15)8-11-25(16,22)3/h12,16-18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,17-,18-,20+,21-,22-,23+,25-,26+,27+/m0/s1
InChI=1S/C27H44O6/c1-24(2,32)10-9-23(31)27(5,33)22-7-6-16-15-12-19(28)18-13-20(29)21(30)14-26(18,4)17(15)8-11-25(16,22)3/h12,16-18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,17+,18-,20-,21+,22+,23-,25+,26-,27-/m1/s1 |
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| CI-MS (NH3) m/z | 482 (M+NH4)+, 465 (MH)+, 447, 429, 411, 364, 347 (M- (C22-C27))+, 329, 313, 311 | | EI-MS m/z (relative intensity %) | | | R-MS | | | FAB-MS m/z | 465 [M+H] (100), 447 [M+H-H2O] (10), 429 [M+H-2H2O] (11), 347 (14), 329 (9), 301 (16), 227 (14) |
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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 | |
| CD3OD | | 01 | 37.32 | | 02 | 68.65 | | 03 | 68.51 | | 04 | 33.11 | | 05 | 51.68 | | 06 | 205.90 | | 07 | 122.28 | | 08 | 168.52 | | 09 | 39.27 | | 10 | 39.16 | | 11 | 22.90 | | 12 | 40.54 | | 13 | 46.73 | | 14 | 56.99 | | 15 | 23.47 | | 16 | 22.67 | | 17 | 56.26 | | 18 | 14.66 | | 19 | 24.68 | | 20 | 77.72 | | 21 | 20.97 | | 22 | 78.20 | | 23 | 27.26 | | 24 | 42.32 | | 25 | 71.25 | | 26 | 28.87 | | 27 | 29.89 |
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| CD3OD | | 01-Ha | 1.43 | | 01-He | 1.76 | | 02-Ha | 3.84 | | 03-He | 3.94 | | 04-Ha | 1.68 | | 04-He | 1.68 | | 05-H | 2.38 | | 07-H | 5.63 | | 09-H | 2.67 | | 11-Ha | 1.78 | | 11-He | 1.91 | | 12-Ha | 2.30 | | 12-He | 1.60 | | 14-H | 2.22 | | 15-Ha | 1.67 | | 15-Hb | 1.59 | | 16-Ha | 1.99 | | 16-Hb | 1.70 | | 17-H | 1.83 | | 18-Me | 0.83 | | 19-Me | 0.97 | | 20-H | - | | 21-Me | 1.23 | | 22-H | 3.31 | | 23-Ha | 1.60 | | 23-Hb | 1.22 | | 24-Ha | 1.80 | | 24-Hb | 1.43 | | 25-H | - | | 26-Me | 1.19 | | 27-Me | 1.21 |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3375 (OH), 1653 (C=O), 1058 (C-O), | | UV (EtOH) λ max (log ε) | |
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| HPTLC | | | TLC | | | GLC | | | HPLC | Retention volume 21.3 ml (column Zorbax-SIL, 250 mm long, 4.6 mm i.d., solvent dichloromethane-isopropanol-water 125: 20: 1.5 v/v/v, flow-rate 1 ml.min-1) |
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Drosophila melanogaster BII cell assay: EC50 = 3.0 x 10-8M (14a-H); EC50 = 8.3 x 10-7M (14b-H) | Drosophila melanogaster BII cell assay: EC50 = 2.2 x 10-8M (14a-H) |
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| General | CANONICA, L. et al. (1976) In: B. Marini-Bettolo, Elsevier, Amsterdam, pp. 211-224 |
 | | General | CANONICA, L. et al. (1980) 12th International Symp. on the Chem. of Nat. Products, Tenerife, |
| | First isolation | THIRY, E. et al. (1988) Dissertation thesis, University of Ulm, |
| | General | HOFFMANN, K.H. et al. (1990) Z. Naturforsch. 45C, 703-708 |
| | Bioactivities | DINAN, L. et al. (1999) J. Computer-aided Mol. Design 13, 185-207 |
| | Bioactivities | HARMATHA, J. et al. (2002) Insect Biochem. Molec. Biol. 32, 181-185 |
| | Identification | HARMATHA, J. et al. (2002) Steroids 67, 127-135 |
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Permanent link to this datasheet: 14-DEOXY-20-HYDROXYECDYSONE
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