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CHEBI:68981 - longirostrerone B

ChEBI IDCHEBI:68981
ChEBI Namelongirostrerone B
Stars
DefinitionAn azaphilone that is 7,8-dihydro-6H-isochromen-6-one substituted by a hydroxy group at position 7, a 4-hydroxy-2-methyl-6-oxocyclohexyl group at position 3, a methyl group at position 7 and a 5,7,9-trimethyl-2-oxoundeca-3,5-dien-1-yl group at position 8. Isolated from Chaetomium longirostre, it exhibits cytotoxic and antimalarial activities.
Secondary ChEBI IDCHEBI:68772
Last Modified7 February 2018
DownloadsMolfile
FormulaC31H42O6
Net Charge0
Average Mass510.671
Monoisotopic Mass510.29814
SMILESCCC(C)CC(C)/C=C(C)/C=C/C(=O)C[C@H]1C2=COC([C@H]3C(=O)C[C@H](O)C[C@@H]3C)=CC2=CC(=O)[C@]1(C)O
InChIInChI=1S/C31H42O6/c1-7-18(2)10-20(4)11-19(3)8-9-23(32)15-26-25-17-37-28(13-22(25)14-29(35)31(26,6)36)30-21(5)12-24(33)16-27(30)34/h8-9,11,13-14,17-18,20-21,24,26,30,33,36H,7,10,12,15-16H2,1-6H3/b9-8+,19-11+/t18?,20?,21-,24+,26-,30+,31+/m0/s1
InChIKeyPZWVXQVKPAZYRZ-GIIUFEGQSA-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 B (CHEBI:68981) has role Chaetomium metabolite (CHEBI:76960)
longirostrerone B (CHEBI:68981) has role antimalarial (CHEBI:38068)
longirostrerone B (CHEBI:68981) has role antineoplastic agent (CHEBI:35610)
longirostrerone B (CHEBI:68981) is a azaphilone (CHEBI:50941)
longirostrerone B (CHEBI:68981) is a enone (CHEBI:51689)
longirostrerone B (CHEBI:68981) is a organic heterobicyclic compound (CHEBI:27171)
longirostrerone B (CHEBI:68981) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name 
(7R,8S)-7-hydroxy-3-[(1S,2S,4R)-4-hydroxy-2-methyl-6-oxocyclohexyl]-7-methyl-8-[(3E,5E)-5,7,9-trimethyl-2-oxoundeca-3,5-dien-1-yl]-7,8-dihydro-6H-isochromen-6-one
Synonym  Source
7-hydroxy-3-(4-hydroxy-6-methyl-2-oxocyclohexyl)-8-(5,7,9-trimethylundeca-3,5-dienoyl)-(7R)-7-methyl-8-hydro-7H-furo-[2,3-h]isochromene-6,18-dioneChEBI
Registry NumbersSources
Reaxys:22123574Reaxys
Citations