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Year of first isolation: |
1984 |
| Formula: | C29H47O11P |
| Molecular weight: | 602 |
| Occurence in plants: |
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| Occurence in animals: |
Schistocerca gregaria [Orthoptera] »  ![Wikipedia: Schistocerca gregaria [Orthoptera]](/images/wikipedia.png)
Locusta migratoria [Orthoptera] »
Labidura riparia [Dermaptera] »
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| Canonical SMILES | | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1OP(=O)([O-])[O-])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)-3-acetoxy-14-hydroxy-10,13-dimethyl-6-oxo-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl phosphate | | CAS-RN | | | PubChem CID | | InChiKey
[ ChemIDPlus: search ] | ZOBGNTMEECHANU-FORVDKSSSA-L | | InChI | InChI=1S/C29H47O11P/c1-16(30)39-21-14-19-20(31)13-18-17(26(19,4)15-22(21)40-41(36,37)38)7-11-27(5)23(8-12-29(18,27)35)28(6,34)24(32)9-10-25(2,3)33/h13,17,19,21-24,32-35H,7-12,14-15H2,1-6H3,(H2,36,37,38)/p-2/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1 |
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| EI-MS m/z (relative intensity %) | | | FAB-MS m/z | 623 (M-H+Na)-, 601 (M-H)-, 585, 583, 569, 541, 483, 467, 439, 396, 371, 319, 215, 183, 181, 149, 123, 97, 79 | | HR-MS | |
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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 | | | 28 | | | 29 | |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 03-He | | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | | | 09-Ha | | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 14-H | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.885 (s ) | | 19-Me | 0.995 (s ) | | 21-Me | 1.19 (s ) | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 25-H | | | 26-Me | 1.19 (s ) | | 27-Me | 1.20 (s ) | | O-Ac | 2.09 (s ) |
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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 | | | GLC | | | HPLC | RP-HPLC with ion suppression, Retention volume 22 ml (Waters column Resolve 15 cm x 4.6 mm i.d. eluted with MeOH-20 mM sodium citrate pH 6.5, 3:7 v/v, flow-rate 1 ml.min-1). |
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| First isolation | ISAAC, R.E. et al. (1984) Biochem. J. 231, 459-464 |
 | | First isolation | MODDE, J.-F. et al. (1984) Int. J. Invertebr. Reprod. Develop. 7, 161-183 |
| | General | DIEHL, P.A. et al. (1985) Methods Enzymol. 111, 377-410 |
| | General | HETRU, C. et al. (1985) Methods Enzymol. 111, 411-419 |
| | General | SAYAH, F. et al. (1995) Netherl. J. Zool. 45, 89-92 |
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Permanent link to this datasheet: 20-HYDROXYECDYSONE 3-ACETATE 2-PHOSPHATE
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