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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:24:39 UTC
Update Date2022-03-07 02:53:48 UTC
HMDB IDHMDB0033659
Secondary Accession Numbers
  • HMDB33659
Metabolite Identification
Common NameDihydrohydroxy-O-methylsterigmatocystin
DescriptionDihydrohydroxy-O-methylsterigmatocystin 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. Dihydrohydroxy-O-methylsterigmatocystin is an extremely weak basic (essentially neutral) compound (based on its pKa). Mycotoxin production by Aspergillus parasiticus.
Structure
Data?1563862440
SynonymsNot Available
Chemical FormulaC19H16O7
Average Molecular Weight356.3261
Monoisotopic Molecular Weight356.089602866
IUPAC Name5-hydroxy-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one
Traditional Name5-hydroxy-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one
CAS Registry Number30099-66-2
SMILES
COC1=CC2=C(C3CC(O)OC3O2)C2=C1C(=O)C1=C(OC)C=CC=C1O2
InChI Identifier
InChI=1S/C19H16O7/c1-22-9-4-3-5-10-15(9)17(21)16-11(23-2)7-12-14(18(16)24-10)8-6-13(20)26-19(8)25-12/h3-5,7-8,13,19-20H,6H2,1-2H3
InChI KeyATDWDHGTLHHXNU-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP1.43ALOGPS
logP1.99ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.38ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.23 m³·mol⁻¹ChemAxon
Polarizability35.51 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]+180.8431661259
DarkChem[M-H]-180.16731661259
DeepCCS[M+H]+179.33930932474
DeepCCS[M-H]-176.98130932474
DeepCCS[M-2H]-210.92530932474
DeepCCS[M+Na]+186.15330932474
AllCCS[M+H]+182.332859911
AllCCS[M+H-H2O]+179.132859911
AllCCS[M+NH4]+185.232859911
AllCCS[M+Na]+186.132859911
AllCCS[M-H]-187.332859911
AllCCS[M+Na-2H]-186.732859911
AllCCS[M+HCOO]-186.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dihydrohydroxy-O-methylsterigmatocystinCOC1=CC2=C(C3CC(O)OC3O2)C2=C1C(=O)C1=C(OC)C=CC=C1O24467.0Standard polar33892256
Dihydrohydroxy-O-methylsterigmatocystinCOC1=CC2=C(C3CC(O)OC3O2)C2=C1C(=O)C1=C(OC)C=CC=C1O23117.5Standard non polar33892256
Dihydrohydroxy-O-methylsterigmatocystinCOC1=CC2=C(C3CC(O)OC3O2)C2=C1C(=O)C1=C(OC)C=CC=C1O23397.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrohydroxy-O-methylsterigmatocystin,1TMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(OC)C=C3OC4OC(O[Si](C)(C)C)CC4C3=C1O23270.3Semi standard non polar33892256
Dihydrohydroxy-O-methylsterigmatocystin,1TBDMS,isomer #1COC1=CC=CC2=C1C(=O)C1=C(OC)C=C3OC4OC(O[Si](C)(C)C(C)(C)C)CC4C3=C1O23499.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0039000000-4c780c0b2c30d04832032017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin GC-MS (1 TMS) - 70eV, Positivesplash10-01w0-9428300000-d45c7f607ac09be7c1802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 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 - Dihydrohydroxy-O-methylsterigmatocystin 10V, Positive-QTOFsplash10-0a4i-0009000000-6324360793e1e64471042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 20V, Positive-QTOFsplash10-0a4r-0019000000-9d0602e4c794692167832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 40V, Positive-QTOFsplash10-053u-8496000000-55ab00f5a6c8f71c26972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 10V, Negative-QTOFsplash10-0a4i-0009000000-073a9b7d4220a6f804c82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 20V, Negative-QTOFsplash10-0a4r-0019000000-3e603a437a9b2a78799a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 40V, Negative-QTOFsplash10-054p-4093000000-d51bb5066bf99eb5d4ea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 10V, Negative-QTOFsplash10-0a4i-0009000000-076d596c97286a62538b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 20V, Negative-QTOFsplash10-0a4i-0019000000-5042da06204ee0553c2b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 40V, Negative-QTOFsplash10-0ke9-1279000000-a7deba511de553f84a7b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 10V, Positive-QTOFsplash10-0a4i-0009000000-f8475e51a9c84fdc7e762021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 20V, Positive-QTOFsplash10-0a4i-0009000000-3a4e7893aa56931735c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrohydroxy-O-methylsterigmatocystin 40V, Positive-QTOFsplash10-0bt9-0169000000-e030bacd335ff38ac4f02021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB011761
KNApSAcK IDNot Available
Chemspider ID8936022
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10760703
PDB IDNot Available
ChEBI IDNot Available
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.. .