Dihydrosterigmatocystin (CHEM024596)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:48:18 UTC
Update Date2016-11-09 01:17:55 UTC
Accession NumberCHEM024596
Identification
Common NameDihydrosterigmatocystin
ClassSmall Molecule
DescriptionDihydrosterigmatocystin is a mycotoxin of Aspergillus versicolo
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,2-Dihydro-6-methoxy-7-hydroxyfuroxanthoneHMDB
5-HydroxydihydrosterigmatocystinHMDB
Chemical FormulaC18H14O6
Average Molecular Mass326.300 g/mol
Monoisotopic Mass326.079 g/mol
CAS Registry Number6795-16-0
IUPAC Name15-hydroxy-11-methoxy-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 Name15-hydroxy-11-methoxy-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
SMILESCOC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2
InChI IdentifierInChI=1S/C18H14O6/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/h2-4,7-8,18-19H,5-6H2,1H3
InChI KeyRHGQIWVTIHZRLI-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
  • Vinylogous ester
  • Vinylogous acid
  • Tetrahydrofuran
  • Ether
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP2.56ALOGPS
logP3.09ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.58ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity83.61 m³·mol⁻¹ChemAxon
Polarizability32.18 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-1191000000-3169260a64a28510a099Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0v5i-2019000000-18bb22e5571b45faf21cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0019000000-26331fd365b17b31be60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0049000000-ce5d50d5caadee2491e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-2690000000-8fd21453b9e79b63ffc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-ac63595de65f6b74b494Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0029000000-fe1061c93c12df43c49fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2491000000-cdb32ce1175da48f2e88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-fdece4c688aa8992d2aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-73afc3fef5344749693eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-055b-0293000000-391354040c44dbd70bc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-eb8469b649b7c5d99242Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0049000000-55ef06ecfac0c9d504a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06xt-1494000000-795297f194352894e731Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030590
FooDB IDFDB002483
Phenol Explorer IDNot Available
KNApSAcK IDC00023633
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4588884
ChEBI IDNot Available
PubChem Compound ID5486173
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.