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Year of first isolation: |
2003 |
| Formula: | C27H44O6 |
| Molecular weight: | 480 |
| Occurence in plants: |
Diploclisia glaucescens [Menispermaceae] »  ![Wikipedia: Diploclisia glaucescens [Menispermaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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![2-DEOXY-5,20-DIHYDROXYECDYSONE [= 2-DEOXY-POLYPODINE B]](images/ecdy/371.gif)
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| Canonical SMILES | CC12CCC(CC1(C(=O)C=C3C2CCC4(C3(CCC4C(C)(C(CCC(C)(C)O)O)O)O)C)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](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)O)O)O)C)O)C » 
| | IUPAC Name | (3S,5S,9R,10R,13R,14S,17S)-3,5,14-trihydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101249756 | InChiKey
[ ChemIDPlus: search ] | BOTCUEKLRNYPOQ-UOTSDXBQSA-N | | InChI | InChI=1S/C27H44O7/c1-22(2,31)10-9-20(29)25(5,32)19-8-13-26(33)18-14-21(30)27(34)15-16(28)6-11-23(27,3)17(18)7-12-24(19,26)4/h14,16-17,19-20,28-29,31-34H,6-13,15H2,1-5H3/t16-,17-,19-,20+,23+,24+,25+,26+,27+/m0/s1 |
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| EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | | | HR-FABMS (+) m/z | 481.3124 [M+H]+, C27H45O6 requires 481.3165 |
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| C5D5N | | 01 | 24.94 | | 02 | 29.11 | | 03 | 65.81 | | 04 | 36.48 | | 05 | 80.23 | | 06 | 209.31 | | 07 | 119.66 | | 08 | 167.33 | | 09 | 37.03 | | 10 | 42.37 | | 11 | 21.76 | | 12 | 32.02 | | 13 | 48.09 | | 14 | 84.01 | | 15 | 31.60 | | 16 | 21.32 | | 17 | 49.95 | | 18 | 17.80 | | 19 | 17.24 | | 20 | 76.76 | | 21 | 21.62 | | 22 | 77.50 | | 23 | 27.41 | | 24 | 42.57 | | 25 | 69.47 | | 26 | 29.92 | | 27 | 30.07 |
| CD3OD | | 01 | 26.23 | | 02 | 29.92 | | 03 | 67.89 | | 04 | 37.50 | | 05 | 81.68 | | 06 | | | 07 | 121.35 | | 08 | 168.85 | | 09 | 38.71 | | 10 | 43.20 | | 11 | 23.09 | | 12 | 33.45 | | 13 | | | 14 | 85.94 | | 15 | 32.54 | | 16 | 22.27 | | 17 | 52.06 | | 18 | 18.84 | | 19 | 17.92 | | 20 | 78.70 | | 21 | 21.83 | | 22 | 79.24 | | 23 | 23.16 | | 24 | 44.04 | | 25 | 72.10 | | 26 | 29.76 | | 27 | 30.50 |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | | | 02-He | | | 03-He | 4.06 (m) | | 04-Ha | | | 04-He | | | 05-H | | | 07-H | 5.79 (d, 2.2) | | 09-H | 3.28-3.33 | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | | | 18-Me | 0.89 (s) | | 19-Me | 1.18 (s) | | 21-Me | 1.18 (s) | | 22-H | 3.28-3.33 | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-Me | 1.18 (s) | | 27-Me | 1.19 (s) |
| C5D5N | | 01-Ha | 1.57 (brd, 14.1) | | 01-He | 2.17 (m) | | 02-Ha | 1.87 (m) | | 02-He | 1.87 (m) ?? | | 03-He | 4.02 (m, w1/2 = 14.2) | | 04-Ha | 1.75 (brd, 14.4) | | 04-He | 1.97 (brd, 14.4) | | 05-H | - | | 07-H | 6.27 (d, 2.5) | | 09-H | 3.60 (m) | | 11-Ha | 1.79 (m) | | 11-He | 1.88 (m) | | 12-Ha | 2.61 (m) | | 12-He | 2.07 (m) | | 15-Ha | 2.17 (m) | | 15-Hb | 1.90 (m) | | 16-Ha | 2.47 (m) | | 16-Hb | 2.07 (m) | | 17-H | 3.00 (t, 9.0) | | 18-Me | 1.22 (s) | | 19-Me | 1.11 (s) | | 21-Me | 1.60 (s) | | 22-H | 3.88 (brd, 8.5) | | 23-Ha | 1.87 (m) | | 23-Hb | 2.17 (m) | | 24-Ha | 1.82 (m) | | 24-Hb | 2.28 (m) | | 26-Me | 1.37 (s) | | 27-Me | 1.37 (s) |
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| M.P. | 128-130 °C ; | | [α]D25 | + 62.4 ° (c 0.34; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 241 nm (-) ; |
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| HPLC | RP HPLC column STR Prep-ODS 20 mm x 250 mm, 60% H2O-MeOH | | GLC | | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 2-DEOXY-5,20-DIHYDROXYECDYSONE [= 2-DEOXY-POLYPODINE B]
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