1.0 2010-05-03 20:06:17 UTC 2026-04-03 01:07:51 UTC T3D3727 Alternariol SmallMolecule Alternariol (C14H10O5) is a solid organic compound with an average molecular weight of 258.23 g/mol. Alternariol belongs to the coumarins and derivatives, a class of phenylpropanoids and polyketides within the organic compounds. Of exogenous origin, it is a biological metabolite and mycotoxin (PMC6539399) that acts as an endocrine disruptor (PMC6539399). It occurs in the mycelium of Alternaria tenuis, which is responsible for fruit spot on Passiflora species and papaya (Carica papaya), as well as alternaria cone disorder in hops. It is an important contaminant in fruits and cereals and is found in mushrooms. The compound serves as a biological and chemical inhibitor of cholinesterase (EC 3.1.1.8). Specifically, alternariol competitively inhibits acetylcholinesterase. It also acts as an agonist at estrogen receptor beta (ESR2) and estrogen receptor (ESR1). Furthermore, alternariol inhibits the activity of DNA-acting enzymes such as topoisomerase 1 (TOP1), DNA topoisomerase 2-alpha (TOP2A), and DNA topoisomerase 2-beta (TOP2B). These effects are attributed to its high affinity for binding to the DNA minor groove, which results in DNA-intercalating, DNA cross-linking, the induction of DNA repair synthesis, the inhibition of DNA replication, and DNA-damaging activities including single-strand and double-strand DNA breaks. Exposure routes include oral, inhalation, and touch. It has been recorded in various sources, including lubricants, medical devices, food packaging, synthetic textiles, carpets and rugs, and electrical and electronic equipment such as batteries, cell phones, printed circuit boards, capacitors, and wires and cables. It is also associated with the preparation of wort and the preparation of wine or sparkling wine. Regarding health effects, alternariol is associated with an increase in esophageal cancer (PMC6539399) and has a therapeutic effect on endometrial cancer (PMC8657677). Fungal Toxin Food Toxin Natural Toxin Organic Compound Ester Food Toxin Mycotoxin Metabolite Fungal Toxin Natural Compound PFAS 1-Methyl-3,7,9-trihydroxy-6H-Dibenzo(b,D)pyran-6-one 3,4',5-Trihydroxy-6'-methyldibenzo-a-pyrone 3,7,9-Trihydroxy-1-methyl-6H-benzo[c]chromen-6-one 3,7,9-Trihydroxy-1-methyl-6H-dibenzo(b,D)pyran-6-one 3,7,9-Trihydroxy-1-methyl-6H-Dibenzo[b,D]pyran-6-one 3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,D]pyran-6-one, 9CI Alternariol 3,4',5-Trihydroxy-6'-methyl-dibenzo[a]pyrone Alternariol from alternaria SP. AOH C14H10O5 258.2262 258.05282343 3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one alternariol 641-38-3 CC1=CC(O)=CC2=C1C1=C(C(=O)O2)C(O)=CC(O)=C1 InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3 CEBXXEKPIIDJHL-UHFFFAOYSA-N Organic compounds Phenylpropanoids and polyketides Coumarins and derivatives Coumarins and derivatives 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Heteroaromatic compounds Hydrocarbon derivatives Isocoumarins and derivatives Lactones Organic oxides Oxacyclic compounds Polyols Pyranones and derivatives Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Aromatic heteropolycyclic compound Benzenoid Benzopyran Coumarin Heteroaromatic compound Hydrocarbon derivative Isocoumarin Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Polyol Pyran Pyranone Vinylogous acid Aromatic heteropolycyclic compounds benzochromenone phenols Detected and Not Quantified Exogenous Cytoplasm Extracellular Membrane Solid White powder. melting_point 350°C logp 2.49 ALOGPS logs -3.05 ALOGPS solubility 2.28e-01 g/l ALOGPS logp 3.18 ChemAxon pka_strongest_acidic 7.63 ChemAxon pka_strongest_basic -4 ChemAxon iupac 3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one ChemAxon average_mass 258.2262 ChemAxon mono_mass 258.05282343 ChemAxon smiles CC1=CC(O)=CC2=C1C1=C(C(=O)O2)C(O)=CC(O)=C1 ChemAxon formula C14H10O5 ChemAxon inchi InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3 ChemAxon inchikey CEBXXEKPIIDJHL-UHFFFAOYSA-N ChemAxon polar_surface_area 86.99 ChemAxon refractivity 67.92 ChemAxon polarizability 25.14 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Alternariol is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. Alternariol is metabolized by microsomes in the liver, preferentially at aromatic positions. The products of aromatic hydroxylation are either catechols or hydroquinones, which may form reactive semiquinones and quinones or undergo redox cycling. (A2981) No indication of carcinogenicity to humans (not listed by IARC). Alternariol is an altertoxin, which is a toxic metabolite of Alternaria fungi. It is an important contaminant in cereals, vegetables, and fruits, as well as in the ground, on wood or walls. (L1957, A2977) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f726c696c30> Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result. If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. HMDB30831 5359485 CHEMBL519982 4514301 C16838 64983 http://en.wikipedia.org/wiki/Alternariol 18727009 16464542 16194592 17340575 11370295 Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC. Wikipedia. Alternariol. Last Updated 12 April 2010.: http://en.wikipedia.org/wiki/Alternariol BE0000971 Alternariol has demonstrated DNA-damaging activities such as single-strand and double-strand DNA breaks, DNA-intercalating, and DNA cross-linking, as well as induction of DNA repair synthesis and inhibition of DNA replication. These effects are thought to be at least partially due to its ability to bind to the DNA minor groove with high affinity, which inhibits the activity of DNA-acting enzymes such as topoisomerase. (A2977, A2978, A2979) BE0004796 Alternariol has demonstrated DNA-damaging activities such as single-strand and double-strand DNA breaks, DNA-intercalating, and DNA cross-linking, as well as induction of DNA repair synthesis and inhibition of DNA replication. These effects are thought to be at least partially due to its ability to bind to the DNA minor groove with high affinity, which inhibits the activity of DNA-acting enzymes such as topoisomerase. (A2977, A2978, A2979) BE0000742 Alternariol has demonstrated DNA-damaging activities such as single-strand and double-strand DNA breaks, DNA-intercalating, and DNA cross-linking, as well as induction of DNA repair synthesis and inhibition of DNA replication. These effects are thought to be at least partially due to its ability to bind to the DNA minor groove with high affinity, which inhibits the activity of DNA-acting enzymes such as topoisomerase. (A2977, A2978, A2979) BE0002425 Alternariol has demonstrated DNA-damaging activities such as single-strand and double-strand DNA breaks, DNA-intercalating, and DNA cross-linking, as well as induction of DNA repair synthesis and inhibition of DNA replication. These effects are thought to be at least partially due to its ability to bind to the DNA minor groove with high affinity, which inhibits the activity of DNA-acting enzymes such as topoisomerase. (A2977, A2978, A2979) BE0000426 Alternariol competitively inhibits acetylcholinesterase. (A2979) BE0000123 Alternariol is able to act as an agonist at estrogen receptors. (A2979) BE0000792 Alternariol is able to act as an agonist at estrogen receptors. (A2979)