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CHEBI:66611 - nardoperoxide

ChEBI IDCHEBI:66611
ChEBI Namenardoperoxide
Stars
DefinitionA 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,7R,8R stereoisomer). Isolated from Nardostachys chinensis, it exhibits antimalarial activity.
Last Modified15 April 2013
DownloadsMolfile
FormulaC15H22O4
Net Charge0
Average Mass266.337
Monoisotopic Mass266.15181
SMILESCC(C)[C@@]12CC[C@@](C)(OO1)C1=C([C@H](C)CC1=O)[C@H]2O
InChIInChI=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
InChIKeyBDBRZURCDWHOCK-SEWBAHNZSA-N
Species of MetaboliteComponentSourceComments
Nardostachys chinensis (ncbitaxon:179860) root (BTO:0001188) DOI (10.1016/S0040-4039(97)10844-9)
Roles Classification
Chemical Role:
oxidising agent  A substance that removes electrons from another reactant in a redox reaction.
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)
nardoperoxide (CHEBI:66611) has role antimalarial (CHEBI:38068)
nardoperoxide (CHEBI:66611) has role metabolite (CHEBI:25212)
nardoperoxide (CHEBI:66611) is a azulenes (CHEBI:38096)
nardoperoxide (CHEBI:66611) is a enone (CHEBI:51689)
nardoperoxide (CHEBI:66611) is a organic peroxide (CHEBI:25702)
nardoperoxide (CHEBI:66611) is a secondary alcohol (CHEBI:35681)
nardoperoxide (CHEBI:66611) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
(1R,4R,7R,8R)-8-hydroxy-1,4-dimethyl-7-(propan-2-yl)-1,4,5,6,7,8-hexahydro-4,7-epidioxyazulen-3(2H)-one
Registry NumbersSources
Reaxys:8039841Reaxys