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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 08:36:25 UTC
Update Date2019-07-23 09:50:42 UTC
HMDB IDHMDB0128877
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-({11,15-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-17-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Description6-({11,15-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-17-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 17-hydroxy-11,15-dimethoxy-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. It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an aromatic-OH-glucuronidation reaction. This aromatic-OH-glucuronidation occurs in humans.
Structure
Data?1563875442
Synonyms
ValueSource
6-({11,15-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-17-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC25H22O13
Average Molecular Weight530.438
Monoisotopic Molecular Weight530.106040768
IUPAC Name6-({11,15-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),4,10,14,16,18-heptaen-17-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-({11,15-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),4,10,14,16,18-heptaen-17-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(OC)C=C(OC3OC(C(O)C(O)C3O)C(O)=O)C=C1O2
InChI Identifier
InChI=1S/C25H22O13/c1-32-10-5-8(35-25-20(29)18(27)19(28)22(38-25)23(30)31)6-12-15(10)17(26)16-11(33-2)7-13-14(21(16)36-12)9-3-4-34-24(9)37-13/h3-7,9,18-20,22,24-25,27-29H,1-2H3,(H,30,31)
InChI KeyPRVRNUCOEXDUFU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Phenolic glycoside
  • Dibenzopyran
  • 1-o-glucuronide
  • O-glucuronide
  • Xanthene
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Pyranone
  • Pyran
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Hydroxy acid
  • Vinylogous ester
  • Dihydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.13ALOGPS
logP0.34ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area179.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.18 m³·mol⁻¹ChemAxon
Polarizability50.28 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-5302139000-8205f61909f8f822cb44JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nmi-9203850000-85723b0a00b162e398eeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bu0-0009170000-4cb0269fdaea56616753JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-0039000000-2f99964a80855c62119aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-0239000000-f970eae65b17cdf317c1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fb9-1206490000-72f79920c9f87ed8a7ddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1109310000-b9983733fce245f429c1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-3119000000-233c6aa5f0aafb823a8fJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.