CHEBI:68980 - longirostrerone A

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ChEBI Name longirostrerone A
ChEBI ID CHEBI:68980
Definition An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a 4-hydroxy-2-methyl-6-oxocyclohexyl 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:68771
Supplier Information
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Formula C32H40O7
Net Charge 0
Average Mass 536.65580
Monoisotopic Mass 536.27740
InChI InChI=1S/C32H40O7/c1-7-17(2)10-19(4)11-18(3)8-9-24(34)29-30-23-16-38-26(28-20(5)12-22(33)15-25(28)35)13-21(23)14-27(36)32(30,6)39-31(29)37/h8-9,11,13-14,16-17,19-20,22,28-30,33H,7,10,12,15H2,1-6H3/b9-8+,18-11+/t17?,19?,20-,22+,28+,29+,30-,32-/m0/s1
InChIKey IAPUSMZQQSXGDI-QXHNIIHBSA-N
SMILES CCC(C)CC(C)\C=C(C)\C=C\C(=O)[C@@H]1[C@@H]2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)[C@@H]1[C@@H](C)C[C@@H](O)CC1=O
Metabolite of Species Details
Chaetomium longirostre (NCBI:txidtxid669026) Ethyl acetate extract of dried fungal biomass See: PubMed
Chaetomium longirostre (NCBI:txidtxid669026) 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): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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 longirostrerone A (CHEBI:68980) has role Chaetomium metabolite (CHEBI:76960)
longirostrerone A (CHEBI:68980) has role antimalarial (CHEBI:38068)
longirostrerone A (CHEBI:68980) has role antineoplastic agent (CHEBI:35610)
longirostrerone A (CHEBI:68980) is a γ-lactone (CHEBI:37581)
longirostrerone A (CHEBI:68980) is a azaphilone (CHEBI:50941)
longirostrerone A (CHEBI:68980) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name
(6aR,9S,9aR)-3-[(1S,2S,4R)-4-hydroxy-2-methyl-6-oxocyclohexyl]-6a-methyl-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-(4-hydroxy-6-methyl-2-oxocyclohexyl)-18-(4,6,8-trimethyldeca-2,4-dienoyl)-(7R)-7-methyl-8,18-dihydro-7H-furo[2,3-h]isochromene-6,17-dione ChEBI
Registry Number Type Source
22123575 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22004007 PubMed citation Europe PMC
Last Modified
24 October 2013