caribenol B (CHEBI:65581)

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ChEBI Name	caribenol B

ChEBI ID	CHEBI:65581

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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C19H28O3

Net Charge

Average Mass

304.42380

Monoisotopic Mass

304.20384

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

SMILES

[H][C@]12CC[C@H](C)C3=C1[C@](O)([C@@H](C[C@@H]2C)C=C(C)C)[C@](C)(O)C3=O

Metabolite of Species	Details
Pseudopterogorgia elisabethae (NCBI:txid204377)	See: PubMed

Roles Classification
Biological Role(s):	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(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.

ChEBI Ontology
Outgoing	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 α-hydroxy ketone (CHEBI:139592) caribenol B (CHEBI:65581) is a tertiary alcohol (CHEBI:26878)

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

Registry Number	Type	Source
11167805	Reaxys Registry Number	Reaxys

Citation	Type	Source
17715964	PubMed citation	Europe PMC

Last Modified

07 February 2018