Compound: Alternariol
SMILES: O=c1oc2c(c(cc(c2)O)C)c3c1c(O)cc(O)c3
InChIKey: CEBXXEKPIIDJHL-UHFFFAOYSA-N
Synonyms: Alternariol, 641-38-3, 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one, CHEBI:64983, 3,7,9-trihydroxy-1-methylbenzo[c]chromen-6-one, KN9L4260JW, DTXSID80214305, 3,4,4'-Trihydroxy-6'-methyl-2-biphenylcarboxylic acid, gamma lactone, 3,7,9-trihydroxy-1-methylbenzo(c)chromen-6-one, 3,7,9-Trihydroxy-1-methyl-6H-benzo(c)chromen-6-one, RefChem:111529, DTXCID40136796, 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one, AOH, MFCD00133068, NSC638263, 6H-DIBENZO(b,d)PYRAN-6-ONE, 1-METHYL-3,7,9-TRIHYDROXY-, CCRIS 6734, 3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,d)pyran-6-one, BRN 0244839, UNII-KN9L4260JW, Alternariol from Alternaria sp., Alternariol/AOH, CEBXXEKPIIDJHL-UHFFFAOYSA-N, Alternariol (6CI,7CI); 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one; NSC 638263, Epitope ID:886616, 5-18-04-00516 (Beilstein Handbook Reference), CHEMBL519982, MEGxm0_000137, orb1707683, orb3025930, SCHEMBL1096830, Alternariol, analytical standard, SCHEMBL29423320, ACon0_000598, ACon1_001301, 6H-Dibenzo[b,d]pyran-6-one, 3,7,9-trihydroxy-1-methyl-, MSK7256, HY-N6714, BDBM50479267, EX-A16389, MSK7256-100A, MSK7256-100M, AKOS015916292, CS-W020863, FA17330, NSC-638263, Alternariol from Alternaria sp., ~96%, NCGC00180653-01, DA-70737, LS-14270, NCI60_012751, Alternariol solution in Methanol, 100ug/mL, NS00015374, 3,4',5-Trihydroxy-6'-methyldibenzo-a-pyrone, Alternariol solution in Acetonitrile, 100ug/mL, F85636, 3,4',5-trihydroxy-6'-methyldibenzo-alpha-pyrone, 3,7,9-trihydroxy-1-methyl-benzo[c]chromen-6-one, Q410677, BRD-K62196712-001-01-3, 1-Methyl-3,7,9-trihydroxy-6H-Dibenzo(b,D)pyran-6-one, 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one #, Alternariol 3,4',5-Trihydroxy-6'-methyl-dibenzo[a]pyrone, 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one, 9CI, 3,4,4'-trihydroxy-6'-methyl-2-biphenylcarboxylic acid gamma-lactone
Theoretical properties:
molecular_formula: C14H10O5
molecular_weight: 258.23 g/mol
exact_mass: 258.05282342 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 0
heavy_atom_count: 19
topological_polar_surface_area: 87 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 350 °C
Descriptions:
pubchem: Alternariol is a benzochromenone that is 6H-benzo[c]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould Alternaria species, which are the most common mycoflora infecting small grain cereals worldwide. It has a role as a metabolite, a mycotoxin and an EC 3.1.1.8 (cholinesterase) inhibitor. It is a member of phenols and a benzochromenone.
chebi: A benzochromenone that is 6<em>H</em>-benzo[<em>c</em>]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould <em>Alternaria</em> species, which are the most common mycoflora infecting small grain cereals worldwide.
chembl: ALTERNARIOL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Alternariol (commonly abbreviated as AOH) is a toxic metabolite of Alternaria fungi. It is an important contaminant in cereals and fruits.
Alternariol exhibits antifungal and phytotoxic activity. It is reported to  inhibit cholinesterase enzymes. It is also a mycoestrogen.
A 2017 in vitro assay study reported alternariol to be a full androgen agonist.
The acute toxicity of AOH and AME is low, but in vitro the substances show a strong mutagenic and teratogenic effect. The substances are associated with the development of esophageal cancer.