Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:10:48 UTC
Update Date2022-03-07 02:55:33 UTC
HMDB IDHMDB0037921
Secondary Accession Numbers
  • HMDB37921
Metabolite Identification
Common NameAureol
DescriptionAureol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, aureol is considered to be a flavonoid. Aureol has been detected, but not quantified in, several different foods, such as gram beans (Vigna mungo), mung beans (Vigna radiata), pulses, and scarlet beans (Phaseolus coccineus). This could make aureol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Aureol.
Structure
Data?1563863109
Synonyms
ValueSource
1,3,9-Trihydroxy-6H-benzofuro[3,2-c]benzopyran-6-one, 9ciHMDB
Aureol?HMDB
Chemical FormulaC15H8O6
Average Molecular Weight284.2204
Monoisotopic Molecular Weight284.032087988
IUPAC Name3,5,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-9-one
Traditional Nameaureol
CAS Registry Number88478-03-9
SMILES
OC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O
InChI Identifier
InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)20-14-12(8)15(19)21-11-5-7(17)3-9(18)13(11)14/h1-5,16-18H
InChI KeyWIRRQLQRDSREEG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility522 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.8 g/LALOGPS
logP2.64ALOGPS
logP2.09ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.6ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.13 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.6 m³·mol⁻¹ChemAxon
Polarizability27.22 ųChemAxon
Number of Rings4ChemAxon
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]+161.30731661259
DarkChem[M-H]-161.69331661259
DeepCCS[M+H]+167.9630932474
DeepCCS[M-H]-165.60330932474
DeepCCS[M-2H]-198.48930932474
DeepCCS[M+Na]+174.05430932474
AllCCS[M+H]+162.932859911
AllCCS[M+H-H2O]+159.132859911
AllCCS[M+NH4]+166.432859911
AllCCS[M+Na]+167.532859911
AllCCS[M-H]-163.232859911
AllCCS[M+Na-2H]-162.032859911
AllCCS[M+HCOO]-160.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AureolOC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O4560.0Standard polar33892256
AureolOC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O2630.0Standard non polar33892256
AureolOC1=CC2=C(C=C1)C1=C(O2)C2=C(O)C=C(O)C=C2OC1=O3188.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Aureol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC(O)=C213170.5Semi standard non polar33892256
Aureol,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O)C=C2O13128.5Semi standard non polar33892256
Aureol,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C213172.5Semi standard non polar33892256
Aureol,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC(O[Si](C)(C)C)=C213174.9Semi standard non polar33892256
Aureol,2TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC(O)=C213253.2Semi standard non polar33892256
Aureol,2TMS,isomer #3C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C213176.4Semi standard non polar33892256
Aureol,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C213321.9Semi standard non polar33892256
Aureol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC(O)=C213374.4Semi standard non polar33892256
Aureol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O)C=C2O13339.4Semi standard non polar33892256
Aureol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C213380.9Semi standard non polar33892256
Aureol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C213626.5Semi standard non polar33892256
Aureol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C213697.0Semi standard non polar33892256
Aureol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C213623.4Semi standard non polar33892256
Aureol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C213991.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Aureol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0536-0090000000-3a0135632b41aafb912d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aureol GC-MS (3 TMS) - 70eV, Positivesplash10-00g0-3041900000-4e9caaf096a5955551772017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Aureol 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 - Aureol 10V, Positive-QTOFsplash10-000i-0090000000-3486b0a460d7378594452015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 20V, Positive-QTOFsplash10-000i-0090000000-5eab173630209e9ac1722015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 40V, Positive-QTOFsplash10-014i-2290000000-3ffe39b45053ac1c5d392015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 10V, Negative-QTOFsplash10-001i-0090000000-7923569b9bdcb0b46d472015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 20V, Negative-QTOFsplash10-001i-0090000000-068016fc39adcf62bf2f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 40V, Negative-QTOFsplash10-014s-1790000000-d127a211a68b1ba2333a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 10V, Positive-QTOFsplash10-000i-0090000000-3896d645ce486a1e32ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 20V, Positive-QTOFsplash10-000i-0090000000-3896d645ce486a1e32ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 40V, Positive-QTOFsplash10-0ap3-0090000000-7fa7de3ad6d37cc4085f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 10V, Negative-QTOFsplash10-001i-0090000000-279002154c712db975df2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 20V, Negative-QTOFsplash10-001i-0090000000-279002154c712db975df2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Aureol 40V, Negative-QTOFsplash10-0ikc-0090000000-835dab1c475ad6e70fdb2021-09-23Wishart 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 IDFDB017078
KNApSAcK IDC00010048
Chemspider ID4590624
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5491648
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1864221
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
Aureol → 6-({5,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-3-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Aureol → 6-({3,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-14-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Aureol → 6-({3,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11(16),12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails