CHEBI:65560 - callophycoic acid D

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ChEBI Name callophycoic acid D
ChEBI ID CHEBI:65560
Definition 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, 2-[(1S,3S,6S)-3-bromo-6-hydroxy-2,2,6-trimethylcyclohexyl]ethyl and a methyl group at positions 9, 10 and 10 respectively (the 9S,10S,10aR stereoisomer). An isomer of callophycoic acid C, it is isolated from the Fijian red alga Callophycus serratus and exhibits antibacterial, antimalarial and anticancer activities.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H36Br2O4
Net Charge 0
Average Mass 584.38000
Monoisotopic Mass 582.09804
InChI InChI=1S/C27H36Br2O4/c1-25(2)21(27(4,32)12-10-22(25)28)9-11-26(3)19-14-18-13-16(24(30)31)5-7-20(18)33-15-17(19)6-8-23(26)29/h5,7,13,15,19,21-23,32H,6,8-12,14H2,1-4H3,(H,30,31)/t19-,21+,22+,23+,26+,27+/m1/s1
InChIKey JTJHSEFMUWUYLU-KXSKSBKOSA-N
SMILES [H][C@@]12Cc3cc(ccc3OC=C1CC[C@H](Br)[C@@]2(C)CC[C@@H]1[C@@](C)(O)CC[C@H](Br)C1(C)C)C(O)=O
Metabolite of Species Details
Callophycus serratus (NCBI:txid632897) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
Application(s): antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing callophycoic acid D (CHEBI:65560) has role antibacterial agent (CHEBI:33282)
callophycoic acid D (CHEBI:65560) has role antimalarial (CHEBI:38068)
callophycoic acid D (CHEBI:65560) has role antineoplastic agent (CHEBI:35610)
callophycoic acid D (CHEBI:65560) has role metabolite (CHEBI:25212)
callophycoic acid D (CHEBI:65560) is a benzoic acids (CHEBI:22723)
callophycoic acid D (CHEBI:65560) is a cyclic ether (CHEBI:37407)
callophycoic acid D (CHEBI:65560) is a dibenzooxepine (CHEBI:38926)
callophycoic acid D (CHEBI:65560) is a diterpenoid (CHEBI:23849)
callophycoic acid D (CHEBI:65560) is a organobromine compound (CHEBI:37141)
callophycoic acid D (CHEBI:65560) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(9S,10S,10aR)-9-bromo-10-{2-[(1S,3S,6S)-3-bromo-6-hydroxy-2,2,6-trimethylcyclohexyl]ethyl}-10-methyl-7,8,9,10,10a,11-hexahydrodibenzo[b,e]oxepine-2-carboxylic acid
Manual Xref Database
27023090 ChemSpider
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Registry Number Type Source
11167774 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17715978 PubMed citation Europe PMC
Last Modified
03 December 2012