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Year of first isolation: |
2007 |
| Formula: | C34H56O12 |
| Molecular weight: | 656 |
| Occurence in plants: |
Fibraurea tinctoria [Menispermaceae] »  ![Wikipedia: Fibraurea tinctoria [Menispermaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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![FIBRAURECDYSIDE [= MAKISTERONE A 3-β-D-GLUCOSIDE]](images/ecdy/412.gif)
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| Canonical SMILES | CC(CC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC5C(C(C(C(O5)CO)O)O)O)O)C)C)O)O)O)C(C)(C)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C[C@H](C[C@H]([C@@](C)([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)C)C)O)O)O)C(C)(C)O » 
| | IUPAC Name | (2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-17-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | 960506-35-8 | | PubChem CID | 44445723 | InChiKey
[ ChemIDPlus: search ] | MQWJGLSZBHVGLN-VBSSPFTJSA-N | | InChI | InChI=1S/C34H56O12/c1-16(30(2,3)42)11-25(38)33(6,43)24-8-10-34(44)18-12-20(36)19-13-22(45-29-28(41)27(40)26(39)23(15-35)46-29)21(37)14-31(19,4)17(18)7-9-32(24,34)5/h12,16-17,19,21-29,35,37-44H,7-11,13-15H2,1-6H3/t16-,17+,19+,21+,22-,23-,24+,25-,26-,27+,28-,29-,31-,32-,33-,34-/m1/s1 |
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| EI-MS m/z (relative intensity %) | | | HR-FAB-MS | 657.3853 [M+H]+ (calculated for C34H56O12, 657.3850) | | FAB-MS m/z | 657 [M+H]+ |
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| C5D5N | | 01 | 39.0 | | 02 | 67.5 | | 03 | 77.7 | | 04 | 30.6 | | 05 | 51.4 | | 06 | 203.0 | | 07 | 121.6 | | 08 | 166.3 | | 09 | 34.2 | | 10 | 38.7 | | 11 | 21.1 | | 12 | 32.0 | | 13 | 48.1 | | 14 | 84.2 | | 15 | 31.9 | | 16 | 21.4 | | 17 | 50.0 | | 18 | 18.0 | | 19 | 24.1 | | 20 | 77.0 | | 21 | 21.6 | | 22 | 74.7 | | 23 | 34.6 | | 24 | 41.9 | | 25 | 72.1 | | 26 | 26/5 | | 27 | 28.2 | | 28 | 15.5 | | [Glu] 1' | 104.2 | | [Glu] 2' | 74.7 | | [Glu] 3' | 76.6 | | [Glu] 4' | 71.6 | | [Glu] 5' | 78.5 | | [Glu] 6' | 62.6 |
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| C5D5N | | 01-Ha | 1.71 (dd, 12.9, 12.8) | | 01-He | 2.04 (dd, 12.9, 3.7) | | 02-Ha | 4.07 (dd, 12.8, 3.7) | | 03-He | 4.26 | | 04-Ha | 1.68 (m) | | 04-He | 2.16 (m) | | 05-H | 2.90 (m) | | 07-H | 6.18 (d, 3.9) | | 09-H | 3.53 (m) | | 11-Ha | 1.64 (m) | | 11-He | 1.78 (m) | | 12-Ha | 2.50 (ddd, 12.7, 12.6, 4.6) | | 12-He | 2.13 (m) | | 15-Ha | 1.93 | | 15-Hb | 1.93 | | 16-Ha | 2.41 (dd, 9.4, 9.2) | | 16-Hb | 2.09 (m) | | 17-H | 2.89 (m) | | 18-Me | 1.16 (s) | | 19-Me | 0.85 (s) | | 21-Me | 1.54 (s) | | 22-H | 3.94 (d, 10.8) | | 23-Ha | 1.55 (m) | | 23-Hb | 1.55 (m) | | 24-H | 2.25 (m) | | 26-Me | 1.28 (s) | | 27-Me | 1.31 (s) | | 28-Me | 1.05 (d, 6.8) | | [Glu] 1' | 4.85 (d, 7.8) | | [Glu] 2' | 3.99 (dd, 8.3, 7.8) | | [Glu] 3' | 4.16 (dd, 9.1, 8.3) | | [Glu] 4' | 3.12 (dd, 9.1, 8.1) | | [Glu] 5' | 3.86 (dd, 9.1, 5.4) | | [Glu] 6' | 4.48 (dd, 11.6, 1.8) | | [Glu] 6'' | 4.24 (dd, 11.6, 5.4) |
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| M.P. | > 300 °C ; | | [α]D25 | + 128.8 ° (c 0.07; MeOH) | | IR (KBr) ν max (cm-1) | 3380, 2962, 2882, 1648, 1442 | | UV (EtOH) λ max (log ε) | 243 (3.32) |
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Permanent link to this datasheet: FIBRAURECDYSIDE [= MAKISTERONE A 3-β-D-GLUCOSIDE]
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