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callophycoic acid A

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A dibenzooxepine diterpenoid that is hexahydrodibenzo[b,e]oxepine with an isolated double bond between positions 6a and 7 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). It is isolated from the Fijian red alga Callophycus serratus and exhibits antibacterial, antimalarial and anticancer activities.

Term info

Label

callophycoic acid A

Synonyms
  • (9S,10S,10aR)-9-bromo-10-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-10-methyl-6,8,9,10,10a,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-6,8,9,10,10a,11-hexahydrodibenzo[b,e]oxepine-2-carboxylic acid [ IUPAC ]

charge

0

formula

C27H35BrO3

has obo namespace

chebi_ontology

id

CHEBI:65557

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/h7,9-12,15,23,25H,5-6,8,13-14,16-17H2,1-4H3,(H,29,30)/b19-9+/t23-,25+,27+/m1/s1

inchikey

UWOQPCLHJDMFFV-FXSXARLRSA-N

mass

487.46900

monoisotopicmass

486.17696

smiles

[H][C@@]12Cc3cc(ccc3OCC1=CC[C@H](Br)[C@@]2(C)CC\C=C(/C)CCC=C(C)C)C(O)=O