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Year of first isolation: |
1990 |
| Formula: | C27H44O9 |
| Molecular weight: | 512 |
| Occurence in plants: |
Lychnis flos-culculi [Caryophyllaceae] »  ![Wikipedia: Lychnis flos-culculi [Caryophyllaceae]](/images/wikipedia.png)
Silene nutans [Caryophyllaceae] »
Silene viridiflora [Caryophyllaceae] »
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| Occurence in animals: |
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| Canonical SMILES | CC12CCC3C(=CC(=O)C4(C3(CC(C(C4)O)O)C)O)C1(CCC2C(C)(C(CCC(C)(CO)O)O)O)O | Isomeric SMILES
[ PubChem: search | XML ]
[ ChemSpider: search ] | C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CCC(CO)(C)O)O)O)O)C)O)C » 
C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC[C@@](CO)(C)O)O)O)O)C)O)C »
C1[C@]2([C@@](C[C@H]([C@H]1O)O)(C(=O)C=C1[C@@H]2CC[C@]2([C@]1(CC[C@@H]2[C@](C)([C@@H](CC[C@](CO)(C)O)O)O)O)C)O)C »
| | IUPAC Name | (2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6,7-tetrahydroxy-6-methylheptan-2-yl]-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one | | CAS-RN | | | PubChem CID | 12148979 | InChiKey
[ ChemIDPlus: search ] | FVXSLSHKONBKBF-HEEVUBGMSA-N | | InChI | InChI=1S/C27H44O9/c1-22(33,14-28)8-7-20(31)25(4,34)19-6-10-26(35)16-11-21(32)27(36)13-18(30)17(29)12-24(27,3)15(16)5-9-23(19,26)2/h11,15,17-20,28-31,33-36H,5-10,12-14H2,1-4H3/t15-,17-,18+,19-,20+,22?,23+,24+,25+,26+,27+/m0/s1 |
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| CI-MS (NH3) m/z | 513 (M+H)+, 495, 477, 459, 441, 396, 379 (M+H - C22--C27)+, 363, 361, 345 | | EI-MS m/z (relative intensity %) | | | HR-MS | |
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| CD3OD | | 01 | 34.4 | | 02 | 68.6 | | 03 | 70.4 | | 04 | 36.3 | | 05 | 80.4 | | 06 | 202.5 | | 07 | 120.7 | | 08 | 167.7 | | 09 | 39.1 | | 10 | 45.6 | | 11 | 22.6 | | 12 | 32.7 | | 13 | 48.9 | | 14 | 85.2 | | 15 | 31.9 | | 16 | 21.6 | | 17 | 50.6 | | 18 | 18.2 | | 19 | 17.1 | | 20 | 78.0 | | 21 | 21.2 | | 22 | 78.6 | | 23 | 26.7 | | 24 | 37.3 | | 25 | 73.8 | | 26 | 70.9 | | 27 | 23.7 |
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| CD3OD | | 01-Ha | | | 01-He | | | 02-Ha | 3.94 (m ) | | 03-He | 3.97 (m ) | | 04-Ha | | | 04-He | | | 07-H | 5.84 (d, 2.5) | | 09-Ha | 3.14 (m, w1/2=22) | | 11-Ha | | | 11-He | | | 12-Ha | | | 12-He | | | 15-Ha | | | 15-Hb | | | 16-Ha | | | 16-Hb | | | 17-H | 2.35 (m ) | | 18-Me | 0.88 (s ) | | 19-Me | 0.90 (s ) | | 21-Me | 1.20 (s ) | | 22-H | 3.33 (d br, 10) | | 23-Ha | | | 23-Hb | | | 24-Ha | | | 24-Hb | | | 26-CH2-OH | 3.35 (s ) | | 27-Me | 1.14, 1.15 (s ) (2 isomers 25R and 25S) |
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| M.P. | | | [α]D20 | | | IR (KBr) ν max (cm-1) | | | UV (EtOH) λ max (log ε) | |
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| TLC on silica | Rf 0.50 (EtOAc-EtOH-H2O, 8:2:1) (20E 0.61); Rf 0.29 (CHCl3-MeOH-Me2CO, 6:2:1) (20E 0.47) | | RP-HPLC | Retention time 4.7 min [Spherisorb-5ODS2 250 mm x 4.6 mm i.d., solvent ACN- 0.1% TFA in H2O 23:77 v/v, flow-rate 1 ml.min-1] (20E 5.5 min) | | NP-HPLC | Retention time 30.9 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:40:3 v/v/v, flow-rate 1 ml.min-1] (20E : 16.8 min); Retention time 77.2 min [Zorbax-Sil 250 mm x 4.6 mm i.d., solvent CH2Cl2-iPrOH-H2O 125:25:2 v/v/v, flow-rate 1 ml.min-1] (20E 37.4 min) |
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Drosophila melanogaster BII cell assay: EC50 = 4.8 x 10-7M |
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Permanent link to this datasheet: 26-HYDROXYPOLYPODINE B
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