Compound: STERIGMATOCYSTIN
SMILES: O=c1c2c(oc3c1c(O)ccc3)c4c(O[C@@H]5[C@H]4C=CO5)cc2OC
InChIKey: UTSVPXMQSFGQTM-DCXZOGHSSA-N
Synonyms: STERIGMATOCYSTIN, 10048-13-2, DTXSID2021280, CHEBI:18227, 7H-Furo[3',2':4,5]furo[2,3-c]xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3aR,12cS)-, 5F95211S5Z, NSC-201423, NSC-204985, 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3aR-cis)-, 3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one, 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3aR,12cS)-, (3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo(10.8.0.02,9.03,7.014,19)icosa-1,4,9,11,14,16,18-heptaen-13-one, RefChem:185686, DTXCID901280, 15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo(10.8.0.02,9.03,7.014,19)icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one, 233-158-6, NSC 201423, NSC 204985, (3aR,12cS)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one, (3aR,12cS)-8-hydroxy-6-methoxy-3a,12c-dihydro-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one, NSC204985, CCRIS 561, 3a,2':4,5]furo[2,3-c]xanthen-7-one, HSDB 3540, EINECS 233-158-6, WLN: T E6 C6 B655 DO KV PO RO SU&&&TTJ IQ MO1, Sterigmacocystin, UNII-5F95211S5Z, 7H-Furo[3',5]furo[2,3-c]xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, 7H-Furo[3',5]furo[2,3-c]xanthen-7-one, 3a,12c-dihydro-8-hydroxy-6-methoxy-, (3aR-cis)-, UTSVPXMQSFGQTM-DCXZOGHSSA-N, Epitope ID:922750, NCIMech_000632, Sterigmatocystine (Standard), MLS004257378, SCHEMBL620489, STERIGMATOCYSTIN [HSDB], STERIGMATOCYSTIN [IARC], CHEMBL524291, orb1706597, SCHEMBL31622300, HY-N6725R, MSK7239, GLXC-07055, HY-N6725, CCG-35887, EX-A16370, LMPK10000001, MSK7239-100A, NSC201423, AKOS040742652, AS58249, (3AR-cis)3a,12c-dihydro-8-hydroxy-6-methoxy-7H-furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 8-Hydroxy-6-methoxy-3a,12c-dihydro-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one, NCI60_001723, SMR003082510, CS-0034157, NS00021429, ST50826206, C00961, F86359, Q2777979, Sterigmatocystin solution in Acetonitrile, 100ug/mL, 3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furol[3',2':4,5]furo[2,3-c]xanthen-7-one, (12cS,3aR)-8-hydroxy-6-methoxy-12c,3a-dihydroxantheno[4',3'-5,4]furano[2,3-b]f uran-7-one
Theoretical properties:
molecular_formula: C18H12O6
molecular_weight: 324.3 g/mol
exact_mass: 324.06338810 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 1
heavy_atom_count: 24
topological_polar_surface_area: 74.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Pale-yellow crystals
color: Pale-yellow crystals
melting_point: 246 °C with decomp
solubility: Insol in strong aq alkali; sparingly sol in most organic solvents; readily sol in dimethylsulfoxide, chloroform, pyridine
Descriptions:
pubchem: Sterigmatocystin can cause cancer according to an independent committee of scientific and health experts.
chebi: An organic heteropentacyclic compound whose skeleton comprises a xanthene ring system <em>ortho</em>-fused to a dihydrofuranofuran moiety. The parent of the class of sterigmatocystins.
chembl: STERIGMATOCYSTIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses.
Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins as it is the penultimate precursor of aflatoxins B1 and G1. It contains a xanthone nucleus attached to a bifuran structure. Sterigmatocystin is mainly produced by the fungi Aspergillus nidulans and A. versicolor.
It has been reported in mouldy grain, green coffee beans and cheese although information on its occurrence in foods is limited. It appears to occur much less frequently than the aflatoxins, although analytical methods for its determination have not been as sensitive, and so it is possible that small concentrations in food commodities may not always have been detected. Although it is a potent liver carcinogen similar to aflatoxin B1, current knowledge suggests that it is nowhere near as widespread in its occurrence. If this is the true situation it would be justified to consider sterigmatocystin as no more than a risk to consumers in special or unusual circumstances. A number of closely related compounds such as o-methyl sterigmatocystin are known, and some may also occur naturally.