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callophycoic acid B

Go to external page http://purl.obolibrary.org/obo/CHEBI_65558

A dibenzooxepine diterpenoid that is hexahydrodibenzo[b,e]oxepine with an isolated double bond between positions 6 and 6a and is substituted by a bromo, a carboxy, a 3E-4,8-dimethylnona-3,7-dien-1-yl and a methyl group at positions 9, 2, 10 and 10 respectively (the 9S,10S,10aR stereoisomer). An isomer of callophycoic acid A, it is isolated from the Fijian red alga Callophycus serratus and exhibits antibacterial, antimalarial and anticancer activities.

Term info

Label

callophycoic acid B

Synonyms
  • (9S,10S,10aR)-9-bromo-10-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-10-methyl-7,8,9,10,10a,11-hexahydrodibenzo[b,e]oxepine-2-carboxylic acid
database cross reference
Subsets

3_STAR

IUPAC NAME
(9S,10S,10aR)-9-bromo-10-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-10-methyl-7,8,9,10,10a,11-hexahydrodibenzo[b,e]oxepine-2-carboxylic acid [ IUPAC ]

charge

0

formula

C27H35BrO3

has obo namespace

chebi_ontology

id

CHEBI:65558

inchi

InChI=1S/C27H35BrO3/c1-18(2)7-5-8-19(3)9-6-14-27(4)23-16-22-15-20(26(29)30)10-12-24(22)31-17-21(23)11-13-25(27)28/h7,9-10,12,15,17,23,25H,5-6,8,11,13-14,16H2,1-4H3,(H,29,30)/b19-9+/t23-,25+,27+/m1/s1

inchikey

QVXPDENFBGGWAY-FXSXARLRSA-N

mass

487.46900

monoisotopicmass

486.17696

smiles

[H][C@@]12Cc3cc(ccc3OC=C1CC[C@H](Br)[C@@]2(C)CC\C=C(/C)CCC=C(C)C)C(O)=O