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Year of first isolation: |
1997 |
| Formula: | C32H52O10 |
| Molecular weight: | 596 |
| Occurence in plants: |
Limnanthes douglasii [Limnanthaceae] »  ![Wikipedia: Limnanthes douglasii [Limnanthaceae]](/images/wikipedia.png)
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| Occurence in animals: |
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| Canonical SMILES | CC(C)CCC(C(C)(C1CCC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)OC5C(C(C(CO5)O)O)O)O)C)C)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@H](C[C@H]([C@H]1O)O[C@H]1C(C([C@@H](CO1)O)O)O)C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@H](O)CCC(C)C)O)O)C)C » 
| | IUPAC Name | (2S,3R,5R,10R,13R,14S)-17-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-2,14-dihydroxy-10,13-dimethyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 24984733 | InChiKey
[ ChemIDPlus: search ] | YVYGCJBVFDRKJN-BDDLOYOMSA-N | | InChI | InChI=1S/C32H52O10/c1-16(2)6-7-25(36)31(5,39)24-9-11-32(40)18-12-20(33)19-13-23(42-28-27(38)26(37)22(35)15-41-28)21(34)14-29(19,3)17(18)8-10-30(24,32)4/h12,16-17,19,21-28,34-40H,6-11,13-15H2,1-5H3/t17?,19-,21-,22+,23+,24?,25+,26-,27+,28-,29+,30+,31+,32+/m0/s1 |
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| CI-MS (NH3) m/z | 614 (M+H+NH3)+, 597 (M+H)+, 579, 561, 543, 481, 465, 447, 429, 363, 345, 191, 166, 150, 116, 102 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| D2O | | 01 | 37.2 | | 02 | 67.6 | | 03 | 75.3 | | 04 | 29.1 | | 05 | 51.3 | | 06 | | | 07 | 122.1 | | 08 | | | 09 | 34.8 | | 10 | 38.9 | | 11 | 21.0 | | 12 | 31.8 | | 13 | 48.3 | | 14 | 86.3 | | 15 | 31.3 | | 16 | 20.9 | | 17 | 50.1 | | 18 | 18.0 | | 19 | 24.0 | | 20 | 78.9 | | 21 | 20.5 | | 22 | 77.9 | | 23 | 29.8 | | 24 | 36.9 | | 25 | 28.4 | | 26 | 22.6 | | 27 | 23.5 | | C-1' | 101.8 | | C-2' | 73.9 | | C-3' | 77.0 | | C-4' | 70.5 | | C-5' | 66.3 |
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| D2O | | 01-Ha | 1.46 (t, 13.0) | | 01-Hb | 1.98 | | 02-Ha | 4.03 (dt, w1/2 = 22) | | 03-He | 4.15 (m, w1/2 = 8) | | 04-Ha | 1.75 | | 04-He | 1.90 | | 05-H | 2.43 (dd, 13.5, 3.5) | | 07-H | 5.98 (d, 2.5) | | 09-Ha | 3.12 (m, w1/2 = 22) | | 11-Ha | 1.75 | | 11-He | 1.86 | | 12-Ha | 1.95 | | 12-He | 1.75 | | 15-Ha | 2.05* | | 15-Hb | 1.65* | | 16-Ha | 1.85** | | 16-Hb | 1.80** | | 17-H | 2.33 (t, 9.6) | | 18-Me | 0.87 (s ) | | 19-Me | 1.00 (s ) | | 21-Me | 1.23 (s ) | | 22-H | 3.45 (dd, 10.7, 1.4) | | 23-Ha | 1.25 | | 23-Hb | 1.60 | | 24-Ha | 1.37 | | 24-Hb | 1.26 | | 25-H | 1.55 | | 26-Me | 0.89 (d, 6.8) | | 27-Me | 0.91 (d, 6.8) | | s1-H' | 4.48 (d, 7.8) | | s2-H' | 3.33 (dd, 7.8, 9.3) | | s3-H' | 3.47 (t, 9.3) | | s4-H' | 3.65 (ddd, 5.5, 9.2, 10.5) | | s5-H" | 3.29 (dd, 10.5, 11.6) | | s5-H' | 3.96 (dd, 5.5, 11.6) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | 242 (4.00) |
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| HPTLC | | | TLC | | | NP-HPLC | column Zorbax-Sil (250x4.6 mm), solvent cyclohexane-iPrOH-H2O (80:40:3), flow-rate 1 ml.min-1, Ret 8.6 min (20E 12.3 min, PoA 5.4 min); solvent CH2Cl2-iPrOH-H2O (125:50:5), flow-rate 1 ml.min-1, Ret 7.2 min (20E 10.1 min, PoA 4.4 min) | | RP-HPLC | column Spherisob 5ODS2 (250x4.6 mm), solvent 18% ACN-iPrOH (5:2) in 0.1% TFA in H2O, flow-rate 1 ml.min-1, Ret 146.3 min (PoA : 155.1 min). |
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Drosophila melanogaster BII cell assay: EC50 = 1.5 x 10-5M |
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Permanent link to this datasheet: LIMNANTHEOSIDE B
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