CHEBI:65564 - callophycoic acid H

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ChEBI Name callophycoic acid H
ChEBI ID CHEBI:65564
Definition A monohydroxybenzoic acid that is 3-bromo-4-hydroxybenzoic acid substituted at position 5 by a decahydronaphthalen-1-ylmethyl group which in turn is substituted by a bromo, two methyl groups, a methylidene and a 4-methylpent-3-en-1-yl group at positions 6, 5, 8a, 2 and 5 respectively. A diterpenoid isolated from the Fijian red alga Callophycus serratus, it exhibits antibacterial, antimalarial and anticancer activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H36Br2O3
Net Charge 0
Average Mass 568.38100
Monoisotopic Mass 566.10312
InChI InChI=1S/C27H36Br2O3/c1-16(2)7-6-11-27(5)22-9-8-17(3)20(26(22,4)12-10-23(27)29)14-18-13-19(25(31)32)15-21(28)24(18)30/h7,13,15,20,22-23,30H,3,6,8-12,14H2,1-2,4-5H3,(H,31,32)/t20-,22+,23-,26+,27-/m1/s1
InChIKey JGBUIUFDBKKZNT-WBNSUDINSA-N
SMILES [H][C@]12CCC(=C)[C@@H](Cc3cc(cc(Br)c3O)C(O)=O)[C@]1(C)CC[C@@H](Br)[C@]2(C)CCC=C(C)C
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): 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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 H (CHEBI:65564) has role antibacterial agent (CHEBI:33282)
callophycoic acid H (CHEBI:65564) has role antimalarial (CHEBI:38068)
callophycoic acid H (CHEBI:65564) has role antineoplastic agent (CHEBI:35610)
callophycoic acid H (CHEBI:65564) has role metabolite (CHEBI:25212)
callophycoic acid H (CHEBI:65564) is a carbobicyclic compound (CHEBI:36785)
callophycoic acid H (CHEBI:65564) is a diterpenoid (CHEBI:23849)
callophycoic acid H (CHEBI:65564) is a monohydroxybenzoic acid (CHEBI:25389)
callophycoic acid H (CHEBI:65564) is a organobromine compound (CHEBI:37141)
IUPAC Name
3-bromo-5-{[(1R,4aS,5R,6R,8aS)-6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methyl-3-penten-1-yl)decahydro-1-naphthalenyl]methyl}-4-hydroxybenzoic acid
Manual Xref Database
27023093 ChemSpider
View more database links
Registry Number Type Source
11167778 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17715978 PubMed citation Europe PMC
Last Modified
03 December 2012