1.0 2010-04-08 22:11:25 UTC 2015-07-20 23:10:29 UTC FDB014707 8,9-Epoxyaflatoxin B1 Prob. ultimate carcinogen of Aflatoxin B1 2,3-Epoxyaflatoxin B1 is formed due to the metabolism of aflatoxin B1 (AFB1) by ; CYP2A13, an enzyme predominantly expressed in human respiratory tract, but there is no detectable AFB1 epoxide formation by CYP2A6, which was also reported to be involved in the metabolic activation of AFB1. (PMID: 16385575). Aflatoxins are naturally occurring mycotoxins that are produced by many species of Aspergillus, a fungus, most notably Aspergillus flavus and Aspergillus parasiticus. At least 13 different types of aflatoxin are produced in nature. Aflatoxin B1 is considered the most toxic and is produced by both Aspergillus flavus and Aspergillus parasiticus. The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favorable for its growth. Favorable conditions include high moisture content (at least 7%) and high temperature. Aflatoxins B1 (AFB1) are contaminants of improperly stored foods; they are potent genotoxic and carcinogenic compounds, exerting their effects through damage to DNA. They can also induce mutations that increase oxidative damage. (PMID: 17214555). Crops which are frequently affected by Aspergillus contamination include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut). (-)-Aflatoxin B1 15a,16a-epoxide (6AS,7as,8ar,8br)-2,3,6a,7a,8a,8b-hexahydro-4-methoxy-cyclopent[c]oxireno[4',5']furo[3',2':4,5]furo[2,3-H][1]benzopyran-1,10-dione [6AS-(6aa,7ab,8ab,8ba)]-2,3,6a,7a,8a,8b-hexahydro-4-methoxy-cyclopent[c]oxireno[4',5']furo[3',2':4,5]furo[2,3-H][1]benzopyran-1,10-dione 2,3-Epoxyaflatoxin B1 8,9-Epoxy-aflatoxin b1 8,9-Epoxyaflatoxin B1 Aflatoxin B1 2,3-epoxide Aflatoxin B1 8,9-epoxide Aflatoxin B1 8,9-oxide Aflatoxin B1 epoxide Aflatoxin B1 exo-8,9-epoxide Aflatoxin B1 exo-8,9-oxide Aflatoxin B1-2,3-oxide Aflatoxin B1-8,9-epoxide Aflatoxin b1, 2,3-oxide exo-Aflatoxin B1-8,9-epoxide C17H12O7 328.273 328.058302738 12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione 12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione 42583-46-0 COC1=CC2=C(C3C4OC4OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2 InChI=1S/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3 KHBXRZGALJGBPA-UHFFFAOYSA-N belongs to the class of organic compounds known as difurocoumarocyclopentenones. These are polycyclic aromatic compounds containing a cyclopenten-2-one ring fused to the coumarin moiety of the difurocoumarin skeleton. Difurocoumarocyclopentenones Organic compounds Phenylpropanoids and polyketides Coumarins and derivatives Furanocoumarins Aromatic heteropolycyclic compounds 1,3-dioxanes 1-benzopyrans Acetals Alkyl aryl ethers Anisoles Aryl alkyl ketones Coumarans Difurocoumarins Epoxides Heteroaromatic compounds Hydrocarbon derivatives Lactones Organic oxides Oxacyclic compounds Pyranones and derivatives Tetrahydrofurans 1-benzopyran Acetal Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Coumaran Difurocoumarin Difurocoumarocyclopentenone Ether Heteroaromatic compound Hydrocarbon derivative Ketone Lactone Meta-dioxane Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane Pyran Pyranone Tetrahydrofuran Solid logp 1.33 ALOGPS logs -2.32 ALOGPS solubility 1.56e+00 g/l ALOGPS melting_point Mp 300° (phase transition at 230°) logp 1.56 ChemAxon pka_strongest_acidic 17.79 ChemAxon pka_strongest_basic -4 ChemAxon iupac 12-methoxy-5,7,9,20-tetraoxahexacyclo[11.7.0.0^{2,10}.0^{3,8}.0^{4,6}.0^{14,18}]icosa-1(13),2(10),11,14(18)-tetraene-17,19-dione ChemAxon average_mass 328.273 ChemAxon mono_mass 328.058302738 ChemAxon smiles COC1=CC2=C(C3C4OC4OC3O2)C2=C1C1=C(C(=O)CC1)C(=O)O2 ChemAxon formula C17H12O7 ChemAxon inchi InChI=1S/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3 ChemAxon inchikey KHBXRZGALJGBPA-UHFFFAOYSA-N ChemAxon polar_surface_area 83.59 ChemAxon refractivity 77.01 ChemAxon polarizability 31.07 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 72155 Specdb::MsMs 95400 Specdb::MsMs 95401 Specdb::MsMs 95402 Specdb::MsMs 159657 Specdb::MsMs 159658 Specdb::MsMs 159659 HMDB06558 #<Reference:0x000055ce324832e8> #<Reference:0x000055ce32483130> Epoxide hydrolase 1 P07099 EPHX1 Glutathione S-transferase A1 P08263 GSTA1 Glutathione S-transferase A2 P09210 GSTA2 Glutathione S-transferase A3 Q16772 GSTA3 Glutathione S-transferase A4 O15217 GSTA4 Glutathione S-transferase A5 Q7RTV2 GSTA5 Glutathione S-transferase Mu 1 P09488 GSTM1 Glutathione S-transferase Mu 2 P28161 GSTM2 Glutathione S-transferase Mu 3 P21266 GSTM3 Glutathione S-transferase Mu 4 Q03013 GSTM4 Glutathione S-transferase Mu 5 P46439 GSTM5 Glutathione S-transferase omega-1 P78417 GSTO1 Glutathione S-transferase omega-2 Q9H4Y5 GSTO2 Glutathione S-transferase P P09211 GSTP1 Microsomal glutathione S-transferase 1 P10620 MGST1 Microsomal glutathione S-transferase 2 Q99735 MGST2 Microsomal glutathione S-transferase 3 O14880 MGST3