callophycoic acid H (CHEBI:65564)

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CHEBI:65564 - callophycoic acid H

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ChEBI ID	CHEBI:65564
ChEBI Name	callophycoic acid H
Stars
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.
Last Modified	3 December 2012
Downloads	Molfile

Formula	C27H36Br2O3
Net Charge	0
Average Mass	568.390
Monoisotopic Mass	566.10312
SMILES	[H][C@]12CCC(=C)[C@@H](Cc3cc(C(=O)O)cc(Br)c3O)[C@]1(C)CC[C@@H](Br)[C@]2(C)CCC=C(C)C
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

Species of Metabolite	Component	Source	Comments
Callophycus serratus (ncbitaxon:632897)	-	PubMed (17715978)

Roles Classification

Chemical Role:	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:	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.
Applications:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. 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.

ChEBI Ontology

Outgoing Relation(s)
	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 Xrefs	Databases
27023093	ChemSpider

Registry Numbers	Sources
Reaxys:11167778	Reaxys

Citations