callophycoic acid G (CHEBI:65563)

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CHEBI:65563 - callophycoic acid G

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ChEBI ID	CHEBI:65563
ChEBI Name	callophycoic acid G
Stars
Definition	A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted at position 3 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	C27H37BrO3
Net Charge	0
Average Mass	489.494
Monoisotopic Mass	488.19261
SMILES	[H][C@]12CCC(=C)[C@@H](Cc3cc(C(=O)O)ccc3O)[C@]1(C)CC[C@@H](Br)[C@]2(C)CCC=C(C)C
InChI	InChI=1S/C27H37BrO3/c1-17(2)7-6-13-27(5)23-11-8-18(3)21(26(23,4)14-12-24(27)28)16-20-15-19(25(30)31)9-10-22(20)29/h7,9-10,15,21,23-24,29H,3,6,8,11-14,16H2,1-2,4-5H3,(H,30,31)/t21-,23+,24-,26+,27-/m1/s1
InChIKey	QCSKWFANIUTEHG-KDIQAUPYSA-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:	antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. 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 G (CHEBI:65563) has role antibacterial agent (CHEBI:33282)
	callophycoic acid G (CHEBI:65563) has role antimalarial (CHEBI:38068)
	callophycoic acid G (CHEBI:65563) has role antineoplastic agent (CHEBI:35610)
	callophycoic acid G (CHEBI:65563) has role metabolite (CHEBI:25212)
	callophycoic acid G (CHEBI:65563) is a carbobicyclic compound (CHEBI:36785)
	callophycoic acid G (CHEBI:65563) is a diterpenoid (CHEBI:23849)
	callophycoic acid G (CHEBI:65563) is a monohydroxybenzoic acid (CHEBI:25389)
	callophycoic acid G (CHEBI:65563) is a organobromine compound (CHEBI:37141)

IUPAC Name
3-{[(1R,4aS,5R,6R,8aS)-6-bromo-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)decahydronaphthalen-1-yl]methyl}-4-hydroxybenzoic acid

Manual Xrefs	Databases
27023092	ChemSpider

Registry Numbers	Sources
Reaxys:11167777	Reaxys

Citations