caribenol A (CHEBI:65580)

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ChEBI Name	caribenol A

ChEBI ID	CHEBI:65580

Definition	A terpene lactone that is 3,4,5,5a,6,7,7a,10,10a,10b-decahydro-2H-1-oxabenzo[cd]cyclopenta[h]azulen-2-one substituted by a hydroxy group at position 10b and methyl groups at positions 3, 6, 9 and 10a. It is isolated from 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

C19H26O3

Net Charge

Average Mass

302.40790

Monoisotopic Mass

302.18819

InChI

InChI=1S/C19H26O3/c1-10-7-13-8-12(3)14-6-5-11(2)15-16(14)19(21,22-17(15)20)18(13,4)9-10/h7,11-14,21H,5-6,8-9H2,1-4H3/t11-,12-,13-,14+,18-,19+/m0/s1

InChIKey

JHCPXISTONUFKB-UUBMZHIOSA-N

SMILES

[H][C@]12CC[C@H](C)C3=C1[C@@](O)(OC3=O)[C@@]1(C)CC(C)=C[C@@]1([H])C[C@@H]2C

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

Roles Classification
Biological Role(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. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.

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. antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.

ChEBI Ontology
Outgoing	caribenol A (CHEBI:65580) has role antimalarial (CHEBI:38068) caribenol A (CHEBI:65580) has role antitubercular agent (CHEBI:33231) caribenol A (CHEBI:65580) has role metabolite (CHEBI:25212) caribenol A (CHEBI:65580) is a organic heterotetracyclic compound (CHEBI:38163) caribenol A (CHEBI:65580) is a terpene lactone (CHEBI:37668) caribenol A (CHEBI:65580) is a tertiary alcohol (CHEBI:26878)

IUPAC Name

(3S,5aR,6S,7aR,10aS,10bS)-10b-hydroxy-3,6,9,10a-tetramethyl-3,4,5,5a,6,7,7a,10,10a,10b-decahydro-2H-1-oxabenzo[cd]cyclopenta[h]azulen-2-one

Registry Number	Type	Source
11167804	Reaxys Registry Number	Reaxys

Last Modified

06 December 2012