caribenol B (CHEBI:65581)

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CHEBI:65581 - caribenol B

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ChEBI ID	CHEBI:65581
ChEBI Name	caribenol B
Stars
Definition	A cyclic terpene ketone that is 2a,3,4,5,5a,6,7,8-octahydroacenaphthylen-1(2H)-one substituted by hydroxy groups at positions 2 and 2a, methyl groups at positions 2, 5 and 8 and a 2-methylprop-1-en-1-yl group at position 3. It is isolated from the the West Indian gorgonian octocoral Pseudopterogorgia elisabethae and exhibits antitubercular and antimalarial activity.
Last Modified	7 February 2018
Downloads	Molfile

Formula	C19H28O3
Net Charge	0
Average Mass	304.430
Monoisotopic Mass	304.20384
SMILES	[H][C@]12CC[C@H](C)C3=C1[C@](O)([C@H](C=C(C)C)C[C@@H]2C)[C@](C)(O)C3=O
InChI	InChI=1S/C19H28O3/c1-10(2)8-13-9-12(4)14-7-6-11(3)15-16(14)19(13,22)18(5,21)17(15)20/h8,11-14,21-22H,6-7,9H2,1-5H3/t11-,12-,13+,14+,18+,19+/m0/s1
InChIKey	UZKZXPWGNRCNCM-NDNLJYSTSA-N

Species of Metabolite	Component	Source	Comments
Pseudopterogorgia elisabethae (ncbitaxon:204377)	-	PubMed (17715964)

Roles Classification

Biological Roles:	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.
Application:	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)
	caribenol B (CHEBI:65581) has role antimalarial (CHEBI:38068)
	caribenol B (CHEBI:65581) has role metabolite (CHEBI:25212)
	caribenol B (CHEBI:65581) is a carbotricyclic compound (CHEBI:38032)
	caribenol B (CHEBI:65581) is a cyclic terpene ketone (CHEBI:36130)
	caribenol B (CHEBI:65581) is a diol (CHEBI:23824)
	caribenol B (CHEBI:65581) is a enone (CHEBI:51689)
	caribenol B (CHEBI:65581) is a tertiary alcohol (CHEBI:26878)
	caribenol B (CHEBI:65581) is a tertiary α-hydroxy ketone (CHEBI:139592)

IUPAC Name
(2S,2aR,3S,5S,5aR,8S)-2,2a-dihydroxy-2,5,8-trimethyl-3-(2-methylprop-1-en-1-yl)-2a,3,4,5,5a,6,7,8-octahydroacenaphthylen-1(2H)-one

Manual Xrefs	Databases
23076462	ChemSpider

Registry Numbers	Sources
Reaxys:11167805	Reaxys

Citations