CHEBI:66612 - isonordoperoxide

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ChEBI Name isonordoperoxide
ChEBI ID CHEBI:66612
Definition A sesquiterpenoid that is 1,4,5,6,7,8-hexahydro-4,7-epidioxyazulen-3(2H)-one substituted by a hydroxy group at position 8, methyl groups at positions 1 and 4 and an isopropyl group at position 7 (the (1R,4R,7S,8S stereoisomer). Isolated from Nardostachys chinensis, it exhibits antimalarial activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C15H22O4
Net Charge 0
Average Mass 266.33280
Monoisotopic Mass 266.15181
InChI InChI=1S/C15H22O4/c1-8(2)15-6-5-14(4,18-19-15)12-10(16)7-9(3)11(12)13(15)17/h8-9,13,17H,5-7H2,1-4H3/t9-,13+,14+,15+/m1/s1
InChIKey BDBRZURCDWHOCK-GBALPHGKSA-N
SMILES CC(C)[C@]12CC[C@](C)(OO1)C1=C([C@H](C)CC1=O)[C@@H]2O
Metabolite of Species Details
Nardostachys chinensis (NCBI:txid179860) Found in root (BTO:0001188). See: DOI
Roles Classification
Chemical Role(s): oxidising agent
A substance that removes electrons from another reactant in a redox reaction.
(via peroxides )
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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing isonordoperoxide (CHEBI:66612) has role antimalarial (CHEBI:38068)
isonordoperoxide (CHEBI:66612) has role metabolite (CHEBI:25212)
isonordoperoxide (CHEBI:66612) is a azulenes (CHEBI:38096)
isonordoperoxide (CHEBI:66612) is a enone (CHEBI:51689)
isonordoperoxide (CHEBI:66612) is a organic peroxide (CHEBI:25702)
isonordoperoxide (CHEBI:66612) is a secondary alcohol (CHEBI:35681)
isonordoperoxide (CHEBI:66612) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name
(1R,4S,7S,8S)-8-hydroxy-1,4-dimethyl-7-(propan-2-yl)-1,4,5,6,7,8-hexahydro-4,7-epidioxyazulen-3(2H)-one
Registry Number Type Source
8039842 Reaxys Registry Number Reaxys
Last Modified
24 April 2013
General Comment
2013-04-15 Tetrahedron Lett. (1998), 39, 1361 - 1364.