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Year of first isolation: |
1982 |
| Formula: | C37H56O11N5P |
| Molecular weight: | 776 |
| Occurence in plants: |
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| Occurence in animals: |
Locusta migratoria [Orthoptera] »  ![Wikipedia: Locusta migratoria [Orthoptera]](/images/wikipedia.png)
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| Canonical SMILES | CC(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CCC(C4)O)C)C)O)C(CCC(C)(C)O)OP(=O)(O)OCC5C(C(C(O5)N6C=NC7=C(N=CN=C76)N)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(CC[C@@H](C4)O)C)C)O)[C@@H](CCC(C)(C)O)OP(=O)(O)OC[C@@H]5[C@H]([C@H]([C@@H](O5)N6C=NC7=C(N=CN=C76)N)O)O » 
| | IUPAC Name | [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2S,3R)-2-[(3S,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-6-methylheptan-3-yl] | | CAS-RN | | | PubChem CID | 21724360 | InChiKey
[ ChemIDPlus: search ] | UQJHEPIKTHIJFC-BSQDPGHISA-N | | InChI | InChI=1S/C37H56N5O11P/c1-19(21-8-13-37(48)23-15-25(44)24-14-20(43)6-11-35(24,4)22(23)7-12-36(21,37)5)26(9-10-34(2,3)47)53-54(49,50)51-16-27-29(45)30(46)33(52-27)42-18-41-28-31(38)39-17-40-32(28)42/h15,17-22,24,26-27,29-30,33,43,45-48H,6-14,16H2,1-5H3,(H,49,50)(H2,38,39,40)/t19-,20-,21+,22-,24-,26+,27+,29+,30+,33+,35+,36+,37+/m0/s1 |
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| CI-MS (NH3) m/z | Direct inlet on gold support: fragments of 2dE + specific fragm at m/z 368, 268, 251, 237, 178, 164, 136 (all found in the MS of AMP) | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| D2O | | 01 | 28.9 (t ) | | 02 | 27.9 (t ) | | 03 | 65.5 (d ) | | 04 | 32.4 (t ) | | 05 | 51.7 (d ) | | 06 | 209.5 (s ) | | 07 | 121.0 (d ) | | 08 | 170.0 (s ) | | 09 | 34.5 (d ) | | 10 | 37.1 (s ) | | 11 | 21.3 (s ) | | 12 | 31.3 (t ) | | 13 | 48.1 (s ) | | 14 | 86.3 (s ) | | 15 | 31.6 (t ) | | 16 | 25.8 (t ) | | 17 | 48.5 (d ) | | 18 | 16.2 (q ) | | 19 | 24.0 (q ) | | 20 | 40.2 (d ) | | 21 | 13.4 (q ) | | 22 | 78.5 (d ) | | 23 | 34.4 (t ) | | 24 | 41.7 (t ) | | 25 | 72.8 (s ) | | 26 | 28.8 (q ) | | 27 | 28.6 (q ) | | A-2 | 153.5 | | A-5 | 116.5 | | A-6 | 156.6 | | A-8 | 141.0 | | F-1' | 89.0 | | F-2´ | 74.8 | | F-3´ | 71.6 | | F-4´ | 86.7 | | F-5´ | 67.5 |
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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 | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | | | 19-Me | | | 21-Me | | | 22-H | | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | | | 27-Me | |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | 3400 (OH), 1640 (cyclohexenone), 1050-1100 (P-O-C). | | UV (EtOH) λ max (log ε) | 250 (?) ; |
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| First isolation | TSOUPRAS, G. et al. (1982) Tetrahedron Lett., 2045-2048 |
 | | General | TSOUPRAS, G. et al. (1983) Tetrahedron 39, 1789-1796 |
| | General | HETRU, C. et al. (1984) C. R. Acad. Sci. Paris, Sér. II, 299, 429-432 |
| | General | HETRU, C. et al. (1985) Methods Enzymol. 111, 411-419 |
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Permanent link to this datasheet: 2-DEOXYECDYSONE 22-ADENOSINE-MONOPHOSPHATE
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