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Search using Accession Number, Compound type, Seaweed Binomial name, IUPAC name, SMILES notation or InChI

 

Accession Number

 

RL282

Compound type

 

Prevezol B

PubChem Compound ID

   

ChemSpider ID

 

9124635 

Molecular Formula

 

C 20 H 33 BrO 3

Molecular Weight [g/mol]

 

401.37822

Monoisotopic Mass [Da]

 

400.16130

Binomial name

 

Laurencia obtusa

Geographical Origin

 

Preveza, Ionean Sea, Greece

Extraction

 

Dichloromethane/Methanol (2:1)

Biological activity

 

Cytotoxic - MCF7(IC 50 =135.6然); PC3(IC 50 =80.4然); HeLa(IC 50 =78.0然); A431(IC 50 =65.2然); K562(IC 50 =76.4然)

Structure Information

 

        

 

IUPAC name

  (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

  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
InChI   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
Predicted Properties    
ALOGPS   3.52   # of Rule of 5 Violations   0
#H-Bond Donor   3   Molar Refractivity [cm3]   101.890
#H-Bond Acceptor   3   Polar Surface Area [2]   60.69
# Freely Rotating Bonds   4   Van der Waals surface area [2]   570.67
Reference   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.
 

 

PMID: 14510540