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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:48 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030588
Secondary Accession Numbers
  • HMDB30588
Metabolite Identification
Common NameSterigmatocystin
DescriptionSterigmatocystin is a mycotoxin of Aspergillus versicolor and Chaetomium species Sterigmatocystin is a poison of the type dermatoxin, from the fungi genus Aspergillus. It appears on crusts of cheese with mold. Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins (compare general fact sheet number 2), and consists of 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 until recently, 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. Sterigmatocystin is a number of closely related compounds such o-methyl sterigmatocystin are known and some may also occur naturally. The IARC-classification of sterigmatocystin is group 2B, which means it is possibly carcinogenic to humans. In practice, the risk is quite low however, because this substance only appears on cheese crusts with mold, and because of that the chance of daily exposure is very low. Sterigmatocystin is a molded crust is best not to be consumed in whole, but after removing the crust, the cheese can still be consumed. Sterigmatocystin is a different kind of mold than that which appears on cheese itself, which can simply be removed before further consumption
Structure
Data?1563862008
Synonyms
ValueSource
3a,12C-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one, 9ciHMDB
SterigmatocystineHMDB
SterigmatocystinMeSH
Chemical FormulaC18H12O6
Average Molecular Weight324.2843
Monoisotopic Molecular Weight324.063388116
IUPAC Name15-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
Traditional Name15-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
CAS Registry Number10048-13-2
SMILES
COC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2
InChI Identifier
InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3
InChI KeyUTSVPXMQSFGQTM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassSterigmatocystins
Sub ClassNot Available
Direct ParentSterigmatocystins
Alternative Parents
Substituents
  • Sterigmatocystin backbone
  • Xanthone
  • Dibenzopyran
  • Xanthene
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Dihydrofuran
  • Vinylogous ester
  • Vinylogous acid
  • Ether
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point246 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.73ALOGPS
logP3.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.38ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity83.7 m³·mol⁻¹ChemAxon
Polarizability31.51 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.98231661259
DarkChem[M-H]-171.54531661259
DeepCCS[M+H]+176.45130932474
DeepCCS[M-H]-174.09330932474
DeepCCS[M-2H]-208.3230932474
DeepCCS[M+Na]+183.85930932474
AllCCS[M+H]+174.032859911
AllCCS[M+H-H2O]+170.532859911
AllCCS[M+NH4]+177.332859911
AllCCS[M+Na]+178.332859911
AllCCS[M-H]-178.532859911
AllCCS[M+Na-2H]-177.532859911
AllCCS[M+HCOO]-176.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SterigmatocystinCOC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O24389.9Standard polar33892256
SterigmatocystinCOC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O22924.6Standard non polar33892256
SterigmatocystinCOC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O22945.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sterigmatocystin,1TMS,isomer #1COC1=CC2=C(C3=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O3)C1C=COC1O23154.2Semi standard non polar33892256
Sterigmatocystin,1TBDMS,isomer #1COC1=CC2=C(C3=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1O3)C1C=COC1O23362.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sterigmatocystin GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-1191000000-0a6fb0c05d0662b97bac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sterigmatocystin GC-MS (1 TMS) - 70eV, Positivesplash10-0fer-2019000000-7b902eddc1918abd0dfd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sterigmatocystin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 10V, Positive-QTOFsplash10-004i-0009000000-57d3fd838ffa3cafae4e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 20V, Positive-QTOFsplash10-004i-0029000000-a3b6c07cd97d495b36412015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 40V, Positive-QTOFsplash10-054o-1492000000-fa083bd25b5fbd8206152015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 10V, Negative-QTOFsplash10-00di-0009000000-46e1583b9996ec69f9ae2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 20V, Negative-QTOFsplash10-00di-0019000000-b69f8ae4547345c5a2ba2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 40V, Negative-QTOFsplash10-0aor-4595000000-461228ac7946dfc708932015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 10V, Positive-QTOFsplash10-004i-0009000000-3ccf9c8a3e8c981e7a462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 20V, Positive-QTOFsplash10-004i-0009000000-3ccf9c8a3e8c981e7a462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 40V, Positive-QTOFsplash10-053r-0392000000-400e743e9316fb4b68482021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 10V, Negative-QTOFsplash10-00di-0009000000-1e58a8f96c64172c0c0f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 20V, Negative-QTOFsplash10-00di-0039000000-91dca4d1af8ba1704d022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sterigmatocystin 40V, Negative-QTOFsplash10-014l-2792000000-0293fe4b2f7e8ea52e842021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002481
KNApSAcK IDC00000563
Chemspider ID4447522
KEGG Compound IDC00961
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSterigmatocystin
METLIN IDNot Available
PubChem Compound5284457
PDB IDNot Available
ChEBI ID18227
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Sterigmatocystin → 3,4,5-trihydroxy-6-({11-methoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-15-yl}oxy)oxane-2-carboxylic aciddetails