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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:24:35 UTC
Update Date2022-03-07 02:53:48 UTC
HMDB IDHMDB0033658
Secondary Accession Numbers
  • HMDB33658
Metabolite Identification
Common NameDe-O-methyldihydrosterigmatocystin
DescriptionDe-O-methyldihydrosterigmatocystin, also known as dihydrodemethylsterigmatocystin, 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. De-O-methyldihydrosterigmatocystin is an extremely weak basic (essentially neutral) compound (based on its pKa). Mycotoxin production by Aspergillus versicolor.
Structure
Data?1563862440
Synonyms
ValueSource
DemethyldihydrosterigmatocystinHMDB
DihydrodemethylsterigmatocystinHMDB
Chemical FormulaC17H12O6
Average Molecular Weight312.2736
Monoisotopic Molecular Weight312.063388116
IUPAC Name11,15-dihydroxy-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 Name11,15-dihydroxy-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 Number30517-66-9
SMILES
OC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2
InChI Identifier
InChI=1S/C17H12O6/c18-8-2-1-3-10-13(8)15(20)14-9(19)6-11-12(16(14)22-10)7-4-5-21-17(7)23-11/h1-3,6-7,17-19H,4-5H2
InChI KeyWUSMTEDKVPWFDN-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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Vinylogous acid
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point202 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP2.42ALOGPS
logP3.59ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.13 m³·mol⁻¹ChemAxon
Polarizability30.12 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]+167.95731661259
DarkChem[M-H]-165.66231661259
DeepCCS[M+H]+169.38130932474
DeepCCS[M-H]-167.02330932474
DeepCCS[M-2H]-200.82330932474
DeepCCS[M+Na]+176.0530932474
AllCCS[M+H]+170.832859911
AllCCS[M+H-H2O]+167.232859911
AllCCS[M+NH4]+174.132859911
AllCCS[M+Na]+175.132859911
AllCCS[M-H]-175.532859911
AllCCS[M+Na-2H]-174.632859911
AllCCS[M+HCOO]-173.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
De-O-methyldihydrosterigmatocystinOC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O24467.7Standard polar33892256
De-O-methyldihydrosterigmatocystinOC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O22922.4Standard non polar33892256
De-O-methyldihydrosterigmatocystinOC1=CC2=C(C3CCOC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O22944.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
De-O-methyldihydrosterigmatocystin,1TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C1=C(O)C=CC=C1O3)C1CCOC1O23121.2Semi standard non polar33892256
De-O-methyldihydrosterigmatocystin,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C3OC4OCCC4C3=C1O23118.2Semi standard non polar33892256
De-O-methyldihydrosterigmatocystin,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C)C=C3OC4OCCC4C3=C1O23199.0Semi standard non polar33892256
De-O-methyldihydrosterigmatocystin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C3=C1C(=O)C1=C(O)C=CC=C1O3)C1CCOC1O23349.7Semi standard non polar33892256
De-O-methyldihydrosterigmatocystin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O)C=C3OC4OCCC4C3=C1O23344.4Semi standard non polar33892256
De-O-methyldihydrosterigmatocystin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C3OC4OCCC4C3=C1O23642.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - De-O-methyldihydrosterigmatocystin GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1190000000-333fc0c025f1a09913402017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - De-O-methyldihydrosterigmatocystin GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-4504900000-8ec5367a9cfefcd1ddae2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - De-O-methyldihydrosterigmatocystin 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 - De-O-methyldihydrosterigmatocystin 10V, Positive-QTOFsplash10-03di-0029000000-68b36ea43dfc30c09a622016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Positive-QTOFsplash10-03di-0089000000-cf4f2b4c6375ec0ef1c12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Positive-QTOFsplash10-01ta-1490000000-30ce98d0cdc6ae50dda82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Negative-QTOFsplash10-03di-0009000000-fdfe47d21a035416c9dc2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Negative-QTOFsplash10-03di-0139000000-f9058f433c1086d6f0ca2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Negative-QTOFsplash10-00ou-1390000000-6148302a8c000974ec2e2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Positive-QTOFsplash10-03di-0009000000-fbd933023572de11abf02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Positive-QTOFsplash10-03di-0009000000-fbd933023572de11abf02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Positive-QTOFsplash10-01ow-0591000000-4fa22d9ff53e113d690c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 10V, Negative-QTOFsplash10-03di-0009000000-b504eaff11e6208b17b12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 20V, Negative-QTOFsplash10-03di-0049000000-3b842f4e2555c65afd0f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - De-O-methyldihydrosterigmatocystin 40V, Negative-QTOFsplash10-029x-1390000000-59c8649686b037aa2c652021-09-25Wishart 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 IDFDB011760
KNApSAcK IDNot Available
Chemspider ID4588953
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5486528
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
De-O-methyldihydrosterigmatocystin → 3,4,5-trihydroxy-6-({11-hydroxy-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
De-O-methyldihydrosterigmatocystin → 3,4,5-trihydroxy-6-({15-hydroxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-11-yl}oxy)oxane-2-carboxylic aciddetails