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callophycoic acid E

Go to external page http://purl.obolibrary.org/obo/CHEBI_65561

A dibenzooxepine diterpenoid that is hexahydrodibenzo[b,e]oxepine-2-carboxylic acid with an isolated double bond between positions 6 and 6a and is substituted by a bromo, a 2-[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]ethyl and a methyl group at positions 9, 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 E

Synonyms
  • (9S,10S,10aR)-9-bromo-10-{2-[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-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-{2-[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-10-methyl-7,8,9,10,10a,11-hexahydrodibenzo[b,e]oxepine-2-carboxylic acid [ IUPAC ]

charge

0

formula

C27H34Br2O3

has obo namespace

chebi_ontology

id

CHEBI:65561

inchi

InChI=1S/C27H34Br2O3/c1-16-5-9-23(28)26(2,3)20(16)11-12-27(4)21-14-19-13-17(25(30)31)6-8-22(19)32-15-18(21)7-10-24(27)29/h6,8,13,15,20-21,23-24H,1,5,7,9-12,14H2,2-4H3,(H,30,31)/t20-,21-,23+,24+,27+/m1/s1

inchikey

PSYSMHVCBGMCIW-FBHGCBBZSA-N

mass

566.36500

monoisotopicmass

564.08747

smiles

[H][C@@]12Cc3cc(ccc3OC=C1CC[C@H](Br)[C@@]2(C)CC[C@@H]1C(=C)CC[C@H](Br)C1(C)C)C(O)=O