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Year of first isolation: |
2002 |
| Formula: | C33H52O11 |
| Molecular weight: | 626 |
| Occurence in plants: |
Silene italica ssp. nemoralis [Caryophyllaceae] »  ![Wikipedia: Silene italica ssp. nemoralis [Caryophyllaceae]](/images/wikipedia.png)
Silene nutans [Caryophyllaceae] »
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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)O)OC5C(C(C(C(O5)CO)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)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O)O)O)C)C » 
| | IUPAC Name | (3S,10R,13R,14S,17S)-17-[(2S,3R)-2,6-dihydroxy-6-methyl-3-[(2R,3R,4S,5R,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 | 11215771 | InChiKey
[ ChemIDPlus: search ] | SVAMEQJUINOPMT-QMZHFZPDSA-N | | InChI | InChI=1S/C33H54O11/c1-29(2,40)10-9-24(44-28-27(39)26(38)25(37)22(16-34)43-28)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 | 627.3744 (C33H53O11 gives 627.3740), 609.3639 (C33H51O10 gives 609.3643) | | CI-MS (NH3) m/z | 644 (M+H+NH3) +, 627 (M+H) +, 609, 591, 497, 479, 461, 447, 429, 411, 393, 375, 347, 329 |
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| D2O | | 01 | 29.3 | | 02 | 28.0 | | 03 | 65.7 | | 04 | 27.5 | | 05 | 52.3 | | 06 | nd | | 07 | 121.8 | | 08 | ND | | 09 | 37.6 | | 10 | 37.6 | | 11 | 21.2 | | 12 | 32.4 | | 13 | 49.3 | | 14 | 86.4 | | 15 | 31.1 | | 16 | 21.4 | | 17 | 50.7 | | 18 | 18.0 | | 19 | 24.1 | | 20 | 78.4 | | 21 | 21.9 | | 22 | 89.1 | | 23 | 26.8 | | 24 | 40.8 | | 25 | 72.7 | | 26 | 28.5 | | 27 | 29.3 | | [glc] 01' | 104.3 | | [glc] 02' | 74.6 | | [glc] 03' | 76.9 | | [glc] 04' | 70.8 | | [glc] 05' | 77.0 | | [glc] 06' | 61.5 |
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| D2O | | 01-Ha | 1.38 | | 01-He | 1.85 | | 02-Ha | 1.38* | | 02-He | 1.65* | | 03-He | 4.12 (m, w1/2 = 24) | | 04-Ha | 1.62 | | 04-He | 1.77 | | 05-H | 2.41 (dd, 12, 2.5) | | 07-H | 5.97 (d, 2.2) | | 09-H | 3.71 (m, w1/2 = 26) | | 11-Ha | 1.71 | | 11-He | 1.85 | | 12-Ha | 1.97 | | 12-He | 1.70 | | 15-Ha | 2.08 (m) | | 15-Hb | 1.65 | | 16-Ha | 1.94 | | 16-Hb | 1.79 | | 17-H | 2.29 (t, 9.5) | | 18-Me | 0.88 (s) | | 19-Me | 0.98 (s) | | 21-Me | 1.29 (s) | | 22-H | 3.65 (br d, 7) | | 23-Ha | 1.55 | | 23-Hb | 1.75 | | 24-Ha | 1.55 | | 24-Hb | 1.97 | | 26-Me | 1.24 (s) | | 27-Me | 1.25 (s) | | [glc] 1´ | 4.54 (d, 7.8) | | [glc] 2´ | 3.38 (dd, 9, 7.8) | | [glc] 3´ | 3.52 (t, 9) | | [glc] 4´ | 3.46 (m) | | [glc] 5´ | 3.46 (m) | | [glc] 6´ | 3.93 (d, 12.5) | | [glc] 6´´ | 3.76 (dd, 12.5, 5) |
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| M.P. | - °C ; | | [α]D20 | ? ° (c ; MeOH) | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | - (-) ; |
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| HPLC | NP-HPLC (Zorbax-SIL, solvent CH2Cl2-iPrOH-H2O 125:40:3), Ret 28 min (2d20E : 8.3 min, 20E 15.6 min)RP-HPLC (Supelco C18, solvent CH3CN-H2O 16.5:83.5), Ret 14.6 min (2d20E 26.2 min, 20E, 7.3 min) | | HPTLC | | | TLC | |
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Permanent link to this datasheet: 2-DEOXY-20-HYDROXYECDYSONE-22-GLUCOSIDE
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