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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:49 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030590
Secondary Accession Numbers
  • HMDB30590
Metabolite Identification
Common NameDihydrosterigmatocystin
DescriptionDihydrosterigmatocystin 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. Dihydrosterigmatocystin is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrosterigmatocystin is a mycotoxin of Aspergillus versicolo.
Structure
Data?1563862008
Synonyms
ValueSource
1,2-Dihydro-6-methoxy-7-hydroxyfuroxanthoneHMDB
5-HydroxydihydrosterigmatocystinHMDB
Chemical FormulaC18H14O6
Average Molecular Weight326.3002
Monoisotopic Molecular Weight326.07903818
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
CAS Registry Number6795-16-0
SMILES
COC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point230 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+174.31331661259
DarkChem[M-H]-172.88931661259
DeepCCS[M+H]+175.65730932474
DeepCCS[M-H]-173.29930932474
DeepCCS[M-2H]-207.40830932474
DeepCCS[M+Na]+182.90830932474
AllCCS[M+H]+174.332859911
AllCCS[M+H-H2O]+170.932859911
AllCCS[M+NH4]+177.532859911
AllCCS[M+Na]+178.532859911
AllCCS[M-H]-180.432859911
AllCCS[M+Na-2H]-179.632859911
AllCCS[M+HCOO]-178.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydrosterigmatocystinCOC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O24414.3Standard polar33892256
DihydrosterigmatocystinCOC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O22964.3Standard non polar33892256
DihydrosterigmatocystinCOC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O23076.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrosterigmatocystin,1TMS,isomer #1COC1=CC2=C(C3=C1C(=O)C1=C(O[Si](C)(C)C)C=CC=C1O3)C1CCOC1O23154.5Semi standard non polar33892256
Dihydrosterigmatocystin,1TBDMS,isomer #1COC1=CC2=C(C3=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1O3)C1CCOC1O23358.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrosterigmatocystin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-1191000000-3169260a64a28510a0992017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrosterigmatocystin GC-MS (1 TMS) - 70eV, Positivesplash10-0v5i-2019000000-18bb22e5571b45faf21c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrosterigmatocystin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrosterigmatocystin 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 - Dihydrosterigmatocystin 10V, Positive-QTOFsplash10-004i-0019000000-26331fd365b17b31be602015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 20V, Positive-QTOFsplash10-004i-0049000000-ce5d50d5caadee2491e42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 40V, Positive-QTOFsplash10-004r-2690000000-8fd21453b9e79b63ffc82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 10V, Negative-QTOFsplash10-004i-0009000000-ac63595de65f6b74b4942015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 20V, Negative-QTOFsplash10-004i-0029000000-fe1061c93c12df43c49f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 40V, Negative-QTOFsplash10-014i-2491000000-cdb32ce1175da48f2e882015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 10V, Positive-QTOFsplash10-004i-0009000000-fdece4c688aa8992d2ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 20V, Positive-QTOFsplash10-004i-0009000000-73afc3fef5344749693e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 40V, Positive-QTOFsplash10-055b-0293000000-391354040c44dbd70bc82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 10V, Negative-QTOFsplash10-004i-0009000000-eb8469b649b7c5d992422021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 20V, Negative-QTOFsplash10-004i-0049000000-55ef06ecfac0c9d504a92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrosterigmatocystin 40V, Negative-QTOFsplash10-06xt-1494000000-795297f194352894e7312021-09-25Wishart 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 IDFDB002483
KNApSAcK IDC00023633
Chemspider ID4588884
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5486173
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.. .

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
Dihydrosterigmatocystin → 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),10,14(19),15,17-hexaen-15-yl}oxy)oxane-2-carboxylic aciddetails