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Year of first isolation: |
2009 |
| Formula: | C33H52O11 |
| Molecular weight: | 626 |
| Occurence in plants: |
Silene gigantea [Caryophyllaceae] »  ![Wikipedia: Silene gigantea [Caryophyllaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC(CC1C(=O)C=C3C2CCC4(C3(CCC4C(C)(C(CCC(C)(C)OC5C(C(C(C(O5)CO)O)O)O)O)O)O)C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H](C1)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)O)O)O)C)C » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14S,17S)-17-[(2R,3R)-2,3-dihydroxy-6-methyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-3,14-dihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 70691110 | InChiKey
[ ChemIDPlus: search ] | ZQUAYJIBFWBUBH-MEVFBLRLSA-N | | InChI | InChI=1S/C33H54O11/c1-29(2,44-28-27(40)26(39)25(38)22(16-34)43-28)10-9-24(37)32(5,41)23-8-13-33(42)19-15-21(36)20-14-17(35)6-11-30(20,3)18(19)7-12-31(23,33)4/h15,17-18,20,22-28,34-35,37-42H,6-14,16H2,1-5H3/t17-,18-,20-,22+,23-,24+,25+,26-,27+,28-,30+,31+,32+,33+/m0/s1 |
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| HR-MS | | | EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | 644 [M+NH4]+, 626 [M]+, 610, 592, 492, 465, 447, 429, 411, 346, 329 |
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| D2O | | 01 | 29.3 | | 02 | 28.1 | | 03 | 65.8 | | 04 | 32.7 | | 05 | 52.3 | | 06 | n.d. n.d. | | 07 | 122.0 | | 08 | n.d. n.d. | | 09 | 36.7 | | 10 | 37.7 | | 11 | 21.3 | | 12 | 32.3 | | 13 | 48.9 | | 14 | 86.8 | | 15 | 31.3 | | 16 | 21.3 | | 17 | 50.3 | | 18 | 18.2 | | 19 | 24.2 | | 20 | 78.2 | | 21 | 20.6 | | 22 | 78.2 | | 23 | 26.8 | | 24 | 39.7 | | 25 | 80.9 | | 26 | 26.9 | | 27 | 26.9 | | C1' | 97.8 | | C2' | 74.6 | | C3' | 77.1 | | C4' | 71.2 | | C5' | 77.1 | | C6' | 62.3 |
| CD3OD | | 01 | 29.5 | | 02 | 28.7 | | 03 | 65.3 | | 04 | 33.0 | | 05 | 52.2 | | 06 | | | 07 | 121.9 | | 08 | | | 09 | 37.6 | | 10 | 37.6 | | 11 | 21.4 | | 12 | 32.6 | | 13 | 49.1 | | 14 | 85.6 | | 15 | 32.6 | | 16 | 21.4 | | 17 | 50.3 | | 18 | 17.8 | | 19 | 24.2 | | 20 | 77.6 | | 21 | 20.8 | | 22 | 78.5 | | 23 | 26.5 | | 24 | 39.8 | | 25 | 78.6 | | 26 | 27.2 | | 27 | 27.2 | | C1' | 98.5 | | C2' | 75.0 | | C3' | 78.0 | | C4' | 71.7 | | C5' | 77.6 | | C6' | 92.8 |
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| D2O | | 01-Ha | 1.35 | | 01-He | 1.68 | | 02-Ha | 1.87 | | 02-He | 1.69 | | 03-He | 4.14 (m, br, w1/2 = 18) | | 04-Ha | 1.63 | | 04-He | 1.76 | | 05-H | 2.42 (d, br, 12) | | 07-H | 5.99 (d, 2.4) | | 09-H | 3.18 (m, br, w1/2 = 26) | | 11-Ha | 1.69 | | 11-He | 1.82 | | 12-Ha | 1.97 | | 12-He | 1.91 | | 15-Ha | 1.67 | | 15-Hb | 2.09 | | 16-Ha | 1.81* | | 16-Hb | 1.91* | | 17-H | 2.35 (t, 9.5) | | 18-Me | 0.88 (s) | | 19-Me | 1.00 (s) | | 21-Me | 1.25 (s) | | 22-H | 3.44 (d, 9.7) | | 23-Ha | 1.73 | | 23-Hb | 1.39 | | 24-Ha | 1.86 | | 24-Hb | 1.61 | | 26-Me | 1.30 (s) | | 27-Me | 1.30 (s) | | H-1' | 4.67 (d, 8.1) | | H-2' | 3.23 (dd, 9.3, 8.1) | | H-3' | 3.53 (t, 9.3) | | H-4' | 3.37 (t, 9.3) | | H-5' | 3.48 (m) | | H-6" | 3.70 (dd, 12.5, 6.6) | | H-6' | 3.92 (dd, 12.5, 2.3) |
| CD3OD | | 01-Ha | 1.36 | | 01-He | 1.61 | | 02-Ha | 1.83 | | 02-He | 1.70 | | 03-He | 3.99 | | 04-Ha | 1.59 | | 04-He | 1.85 | | 05-H | 2.43 (dd, 12.5, 4.2) | | 07-H | 5.81 (d, 2.1) | | 09-H | 3.15 (m) | | 11-Ha | 1.70 | | 11-He | 1.74 | | 12-Ha | 2.12 | | 12-He | 1.82 | | 15-Ha | 1.61 | | 15-Hb | 1.98 | | 16-Ha | 1.76* | | 16-Hb | 1.98* | | 17-H | 2.40 (m) | | 18-Me | 0.89 (s) | | 19-Me | 0.96 (s) | | 21-Me | 1.19 (s) | | 22-H | 3.36 (d) | | 23-Ha | 1.75 | | 23-Hb | 1.46 | | 24-Ha | 1.96 | | 24-Hb | 1.51 | | 26-Me | 1.27 (s) | | 27-Me | 1.28 (s) | | H-1' | 4.46 (d, 7.9) | | H-2' | 3.17 (dd, 9.5, 8.1) | | H-3' | 3.36 | | H-4' | 3.24 | | H-5' | 3.26 | | H-6" | 3.65 | | H-6' | 3.88 (dd, 11.6, 1.8) |
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| M.P. | °C ; | | [α]D20 | ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 242 () ; |
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Permanent link to this datasheet: 2-DEOXY-20-HYDROXYECDYSONE 25-GLUCOSIDE
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