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Accession Number |
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RL282 |
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Compound type |
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Prevezol B |
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PubChem Compound ID |
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ChemSpider ID |
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9124635 |
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Molecular Formula |
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C 20 H 33 BrO 3 |
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Molecular Weight [g/mol] |
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401.37822 |
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Monoisotopic Mass [Da] |
|
400.16130 |
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Binomial name |
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Laurencia obtusa |
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Geographical Origin |
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Preveza, Ionean Sea, Greece |
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Extraction |
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Dichloromethane/Methanol (2:1) |
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Biological activity |
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Cytotoxic - MCF7(IC 50 =135.6µM); PC3(IC 50
=80.4µM); HeLa(IC 50 =78.0µM); A431(IC 50
=65.2µM); K562(IC 50 =76.4µM) |
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Structure Information |
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IUPAC name |
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(1S,2S,3R,4S)-3-{2-[(1R,3R,4S)-3-bromo-4-hydroxy-4-methylcyclohexyl]prop-2-en-1-yl}-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol |
|
SMILES notation |
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C[C@]1(O)CC[C@H](C[C@H]1Br)C(/C[C@@H]2[C@H](CC[C@](C)(O)[C@H]2O)C(=C)C)=C |
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InChI |
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InChI=1/C20H33BrO3/c1-12(2)15-7-9-20(5,24)18(22)16(15)10-13(3)14-6-8-19(4,23)17(21)11-14/h14-18,22-24H,1,3,6-11H2,2,4-5H3/t14-,15-,16-,17-,18+,19+,20+/m1/s1 |
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Predicted Properties |
|
|
|
ALOGPS |
|
3.52 |
|
# of Rule of 5 Violations |
|
0 |
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#H-Bond Donor |
|
3 |
|
Molar Refractivity [cm3] |
|
101.890 |
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#H-Bond Acceptor |
|
3 |
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Polar Surface Area [Å2] |
|
60.69 |
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# Freely Rotating Bonds |
|
4 |
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Van der Waals surface area [Å2] |
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570.67 |
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Reference |
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Novel Cytotoxic Brominated Diterpenes from the Red Alga
Laurencia obtusa. Iliopoulou D, Mihopoulos N, Vagias C,
Papazafiri P, Roussis V. J. Org. Chem. 2003: 68 (20); 7667-74. |
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PMID: 14510540 |
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