CHEBI:68981 - longirostrerone B

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name longirostrerone B
ChEBI ID CHEBI:68981
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:68772
Supplier Information
Download Molfile XML SDF
Formula C31H42O6
Net Charge 0
Average Mass 510.66160
Monoisotopic Mass 510.29814
InChI InChI=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
InChIKey PZWVXQVKPAZYRZ-GIIUFEGQSA-N
SMILES CCC(C)CC(C)\C=C(C)\C=C\C(=O)C[C@H]1C2=COC(=CC2=CC(=O)[C@]1(C)O)[C@@H]1[C@@H](C)C[C@@H](O)CC1=O
Metabolite of Species Details
Chaetomium longirostre (NCBI:txid669026) Ethyl acetate extract of dried fungal biomass See: PubMed
Chaetomium longirostre (NCBI:txid669026) 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.
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.
(via azaphilone )
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.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-dione ChEBI
Registry Number Type Source
22123574 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22004007 PubMed citation Europe PMC
Last Modified
07 February 2018