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CHEBI:68982 - longirostrerone C

ChEBI IDCHEBI:68982
ChEBI Namelongirostrerone C
Stars
DefinitionAn azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a 6-methyl-2-oxocyclohex-3-en-1-yl group at position 3, a methyl group at position 6a and a 4,6,8-trimethyldeca-2,4-dienoyl group at position 9. Isolated from Chaetomium longirostre, it exhibits cytotoxic and antimalarial activities.
Secondary ChEBI IDCHEBI:68773
Last Modified24 October 2013
DownloadsMolfile
FormulaC32H38O6
Net Charge0
Average Mass518.650
Monoisotopic Mass518.26684
SMILES[H][C@@]12C3=COC([C@H]4C(=O)C=CC[C@@H]4C)=CC3=CC(=O)[C@]1(C)OC(=O)[C@@H]2C(=O)/C=C/C(C)=C/C(C)CC(C)CC
InChIInChI=1S/C32H38O6/c1-7-18(2)13-20(4)14-19(3)11-12-25(34)29-30-23-17-37-26(28-21(5)9-8-10-24(28)33)15-22(23)16-27(35)32(30,6)38-31(29)36/h8,10-12,14-18,20-21,28-30H,7,9,13H2,1-6H3/b12-11+,19-14+/t18?,20?,21-,28+,29+,30-,32-/m0/s1
InChIKeyHOGGEAXXACLKBX-OPYHNVJQSA-N
Species of MetaboliteComponentSourceComments
Chaetomium longirostre (ncbitaxon:669026)
- PubMed (22004007)
- PubMed (22004007) Ethyl acetate extract of dried fungal biomass
Roles Classification
Biological Roles:
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.
Chaetomium metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Chaetomium.
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
Applications:
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
longirostrerone C (CHEBI:68982) has role Chaetomium metabolite (CHEBI:76960)
longirostrerone C (CHEBI:68982) has role antimalarial (CHEBI:38068)
longirostrerone C (CHEBI:68982) has role antineoplastic agent (CHEBI:35610)
longirostrerone C (CHEBI:68982) is a azaphilone (CHEBI:50941)
longirostrerone C (CHEBI:68982) is a organic heterotricyclic compound (CHEBI:26979)
longirostrerone C (CHEBI:68982) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(6aR,9S,9aR)-6a-methyl-3-[(1S,6S)-6-methyl-2-oxocyclohex-3-en-1-yl]-9-[(2E,4E)-4,6,8-trimethyldeca-2,4-dienoyl]-9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione
Synonym  Source
3-(6-methyl-2-oxocyclohex-3-enyl)-18-(4,6,8-trimethyldeca-2,4-dienoyl)-(7R)-7-methyl-8,18-dihydro-7H-furo[2,3-h]isochromene-6,17-dioneChEBI
Registry NumbersSources
Reaxys:22123573Reaxys
Citations