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Year of first isolation: |
1971 |
| Formula: | C39H62O13 |
| Molecular weight: | 738 |
| Occurence in plants: |
Polypodium vulgare [Polypodiaceae] »  ![Wikipedia: Polypodium vulgare [Polypodiaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC1CCC(OC1O)C(C)C2CCC3C2(CCC4C3=CC(=O)C5C4(CCC(C5)OC6C(C(C(C(O6)CO)O)O)OC7C(C(C(C(O7)C)O)O)O)C)C | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@H](C[C@H](C1)O[C@H]1C(C([C@@H](C(O1)CO)O)O)O[C@H]1C(C([C@H](C(O1)C)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H]([C@H]1CC[C@@H]([C@H](O1)O)C)C)C)C » 
| | IUPAC Name | (3S,5S,9R,10R,13R,14R,17R)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-17-[(1S)-1-(6-hydroxy-5-methyloxan-2-yl)ethyl]-10,13-dimethyl-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 101306874 | InChiKey
[ ChemIDPlus: search ] | MLAYKJNHCRIBKC-KUGLUBNCSA-N | | InChI | InChI=1S/C39H62O13/c1-17-6-9-27(50-35(17)47)18(2)22-7-8-23-21-15-26(41)25-14-20(10-12-39(25,5)24(21)11-13-38(22,23)4)49-37-34(32(45)30(43)28(16-40)51-37)52-36-33(46)31(44)29(42)19(3)48-36/h15,17-20,22-25,27-37,40,42-47H,6-14,16H2,1-5H3/t17?,18-,19-,20-,22+,23-,24-,25+,27?,28+,29-,30+,31+,32-,33+,34+,35?,36-,37+,38+,39+/m0/s1 |
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| ESI-MS m/z (relative intensity %) | 658 (2) [M-H+D+Na-C4H8O3]+, 642 (3) [M-H+D+Na-C4H8O4]+, 616 (100), 331 (2) [C12H20O9Na]+ | | HR-ESI-MS | [M+H]+ 739.4236 (calculated for C39H63O13, 739.4263, delta: 3.6 ppm) |
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| CD3OD | | 01 | 37.9 | | 02 | 29.9 | | 03 | 77.6 | | 04 | 27.3 | | 05 | 54.4 | | 06 | 202.6 | | 07 | 123.6 | | 08 | 167.2 | | 09 | 51.4 | | 10 | 39.6 | | 11 | 23.0 | | 12 | 40.1 | | 13 | 46.1 | | 14 | 56.5 | | 15 | 23.8 | | 16 | 28.2 | | 17 | 54.3 | | 18 | 12.8 | | 19 | 13.6 | | 20 | 41.6 | | 21 | 14.4 | | 22 | | | 23 | 25.1 | | 24 | 32.5 | | 25 | 38.9 | | 26 | 102.6 | | 27 | 17.3 | | Glu 1' | 101.1 | | Glu 2' | 79.3 | | Glu 3' | | | Glu 4' | 72.0 | | Glu 5' | 77.9 | | Glu 6' | 63.0 | | Rha 1'' | 102.4 | | Rha 2'' | 72.4 | | Rha 3'' | 72.5 | | Rha 4'' | 74.2 | | Rha 5'' | 70.0 | | Rha 6'' | 18.2 |
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| CD3OD | | 01-Ha; 01-Hb | 1.42; 1.86 | | 02-Ha; 02-Hb | 1.46; 1.90 | | 03-He | 3.80 (tt,11.3, 4.3) | | 04-Ha; 04-Hb | 1.39; 2.33 | | 05-H | 2.35 | | 07-H | 5.67 (t, 2.1) | | 09-Ha | 2.31 | | 11-Ha | 1.69 | | 11-Hb | 1.86 | | 12-Ha | 1.49 | | 12-Hb | 2.17 | | 14-H | 2.18 | | 15-Ha | 1.56 | | 15-Hb | 1.68 | | 16-Ha | 1.47 | | 16-Hb | 1.89 | | 17-H | 1.43 | | 18-Me | 0.67 (s) | | 19-Me | 0.88 (s) | | 20-H | 1.78 | | 21-Me | 1.01 (d, 6.8) | | 22-H | 3.48 | | 23-Ha | 1.32 | | 23-Hb | 1.43 | | 24-Ha; 24-Hb | 1.19; 1.82 | | 25-H | 1.31 | | 26-H | 4.24 (d, 8.3) | | 27-Me | 0.92 (d, 6.5) | | glu H-1' | 4.55 (d, 7.7) | | glu H-2' | 3.37 (dd, 9.3, 7.8) | | glu H-3' | 3.48 (t, 9.1) | | glu H-4' | 3.26 | | glu H-5' | 3.26 | | glu H-6a';H-6b' | 3.65; 3.85 | | rha H-1'' | 5.19 (d, 1.6) | | rha H-2'' | 3.94 (dd, 93.1, 1.8) | | rha H-3'' | 3.73 (dd, 9.5, 3.3) | | rha H-4'' | 3.37 | | rha H-5'' | 4.13 | | rha Me-6'' | 1.24 (d, 6.3) |
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| M.P. | 198-201 °C | | [α]D28 | - 37 ° (c 0.1; MeOH) | | IR (Nujol) ν max (cm-1) | 3450 (OH), 1711 (CO), 1675 (cyclohexenone), 1624 | | UV (EtOH) λ max (log ε) | 246 (4.06) |
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Permanent link to this datasheet: POLYPODOSAPONIN
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