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Year of first isolation: |
2008 |
| Formula: | C33H54O9 |
| Molecular weight: | 594 |
| Occurence in plants: |
Microsorum membranifolium [Polypodiaceae] »  ![Wikipedia: Microsorum membranifolium [Polypodiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1C(C(C(C(O1)OC(C)(C)CCC(C(C)C2CCC3(C2(CCC4C3=CC(=O)C5C4(CCC(C5)O)C)C)O)O)O)O)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@H](C)[C@@H](CCC(C)(C)O[C@H]1OC([C@@H](C(C1O)O)O)C)O)O)C)C » 
| | IUPAC Name | (3S,5R,9R,10R,13R,14S,17R)-3,14-dihydroxy-17-[(2S,3R)-3-hydroxy-6-methyl-6-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyheptan-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101838355 | InChiKey
[ ChemIDPlus: search ] | BDKGGTGFHVGEHI-RKJBTMRNSA-N | | InChI | InChI=1S/C33H54O9/c1-17(24(35)10-11-30(3,4)42-29-28(39)27(38)26(37)18(2)41-29)20-9-14-33(40)22-16-25(36)23-15-19(34)7-12-31(23,5)21(22)8-13-32(20,33)6/h16-21,23-24,26-29,34-35,37-40H,7-15H2,1-6H3/t17-,18-,19-,20+,21-,23-,24+,26-,27+,28+,29-,31+,32+,33+/m0/s1 |
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| HR-MS | | | EI-MS m/z (relative intensity %) | | | CI-MS (NH3) m/z | 612 [M+NH4] +, 595 [M+H]+, 594 [M]+, 577 [MH-H2O]+, 559 [MH-2H2O]+, 448 [M+NH4-sugar]+, 431 [MH-sugar]+, 413 [MH-sugar-H2O]+, 395 [MH-sugar-2H2O]+, 164 [sugar]+ |
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| CD3OD | | 01 | 29.3 | | 02 | 28.9 | | 03 | 65.2 | | 04 | 32.8 | | 05 | 52.1 | | 06 | 206.3 | | 07 | 121.5 | | 08 | 168.6 | | 09 | 37.5 | | 10 | 37.5 | | 11 | 21.8 | | 12 | 32.4 | | 13 | 48.2 | | 14 | 84.9 | | 15 | 31.5 | | 16 | 27.0 | | 17 | 49.1 | | 18 | 15.9 | | 19 | 24.2 | | 20 | 43.3 | | 21 | 13.0 | | 22 | 75.3 | | 23 | 24.8 | | 24 | 40.5 | | 25 | 77.9 | | 26 | 26.4 | | 27 | 26.7 | | [sugar] 1' | 97.1 | | [sugar] 2' | 73.8 | | [sugar] 3' | 72.6 | | [sugar] 4' | 74.2 | | [sugar] 5' | 69.7 | | [sugar] 6' | 17.7 |
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| CD3OD | | 01-Ha | 1.46 | | 01-He | 1.64 | | 02-Ha | 1.66 | | 02-He | 1.82 | | 03-He | 3.98 (m, w1/2 = 23) | | 04-Ha | 1.57 | | 04-He | 1.79 | | 05-H | 2.42 (dd, 12.3, 4.0) | | 07-H | 5.81 (d, br, 2.4) | | 09-H | 3.22 (m, w1/2 = 26) | | 11-Ha | 1.64 | | 11-He | 1.74 | | 12-Ha | 2.09 (m) | | 12-He | 1.77 | | 15-Ha | 1.98 | | 15-Hb | 1.64 | | 16-Ha | 1.96 | | 16-Hb | 1.51 | | 17-H | 2.03 | | 18-Me | 0.73 (s) | | 19-Me | 0.97 (s) | | 20-H | 1.76 | | 21-Me | 0.94 (d, 6.6) | | 22-H | 3.59 (d, br, 10.6) | | 23-Ha | 1.31 | | 23-Hb | 1.58 | | 24-Ha | 1.84 | | 24-Hb | 1.50 | | 26-Me | 1.23 (s) | | 27-Me | 1.25 (s) | | [sugar] 1' | 4.95 (dbr, 1.5)Y | | [sugar] 2' | 3.68 (m) ABXY | | [sugar] 3' | 3.69 (m) ABXY | | [sugar] 4' | 3.34 (t, 9.3) X | | [sugar] 5' | 3.77 (dq, 9.3, 6.3) | | [sugar] 6'-Me | 1.235 (d, 6.3) |
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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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| HPLC | RP-HPLC column ACE C18 (15x0.46 cm) eluted with a linear gradient (15 to 35% acetonitrile/isopropanol (5/2) in 0.1% TFA over 40 min, flow rate 1 mL/min, Ret 28.2 min (20E 9.8 min, 2dE 25.8 min)NP-HPLC column Zorbax-SIL (25x0.46 cm), eluted with cyclohexane/isopropanol/water (100/50/3), flow-rate 1 mL/min, Ret 12.3 min (20E 17.1 min, 2dE 8.5 min) | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 2-DEOXYECDYSONE 25-RHAMNOSIDE
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