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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-04-03 14:10:34 UTC
Update Date2021-10-13 05:41:11 UTC
HMDB IDHMDB0013696
Secondary Accession Numbers
  • HMDB13696
Metabolite Identification
Common NameUrolithin B
DescriptionUrolithin B belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Based on a literature review a significant number of articles have been published on Urolithin B.
Structure
Data?1582753143
Synonyms
ValueSource
3-hydroxy-6H-benzo[c]chromen-6-oneHMDB
3-hydroxy-urolithinHMDB
Chemical FormulaC13H8O3
Average Molecular Weight212.2008
Monoisotopic Molecular Weight212.047344122
IUPAC Name3-hydroxy-6H-benzo[c]chromen-6-one
Traditional Name3-hydroxybenzo[c]chromen-6-one
CAS Registry Number1139-83-9
SMILES
OC1=CC2=C(C=C1)C1=C(C=CC=C1)C(=O)O2
InChI Identifier
InChI=1S/C13H8O3/c14-8-5-6-10-9-3-1-2-4-11(9)13(15)16-12(10)7-8/h1-7,14H
InChI KeyWXUQMTRHPNOXBV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Isocoumarin
  • Benzopyran
  • 1-benzopyran
  • 2-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point432.55 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility576.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.947 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.65ALOGPS
logP2.62ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity58.92 m³·mol⁻¹ChemAxon
Polarizability21.21 ųChemAxon
Number of Rings3ChemAxon
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]+146.14531661259
DarkChem[M-H]-146.04231661259
DeepCCS[M+H]+146.84130932474
DeepCCS[M-H]-144.48330932474
DeepCCS[M-2H]-177.79230932474
DeepCCS[M+Na]+152.93430932474
AllCCS[M+H]+145.132859911
AllCCS[M+H-H2O]+140.832859911
AllCCS[M+NH4]+149.132859911
AllCCS[M+Na]+150.332859911
AllCCS[M-H]-146.732859911
AllCCS[M+Na-2H]-146.132859911
AllCCS[M+HCOO]-145.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Urolithin BOC1=CC2=C(C=C1)C1=C(C=CC=C1)C(=O)O23262.6Standard polar33892256
Urolithin BOC1=CC2=C(C=C1)C1=C(C=CC=C1)C(=O)O22270.5Standard non polar33892256
Urolithin BOC1=CC2=C(C=C1)C1=C(C=CC=C1)C(=O)O22351.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Urolithin B,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=CC=CC=C122450.6Semi standard non polar33892256
Urolithin B,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=CC=CC=C122650.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Urolithin B GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1970000000-fd0fa569b607450a10402017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Urolithin B GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-4290000000-f746cc9bb48d4029b3072017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Urolithin B 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 - Urolithin B 10V, Positive-QTOFsplash10-03di-0090000000-546510672963f873f32b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 20V, Positive-QTOFsplash10-03di-0190000000-171e9d9553181a07d7442015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 40V, Positive-QTOFsplash10-0gbi-2910000000-741662b9391006b4a8af2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 10V, Negative-QTOFsplash10-03di-0190000000-7bf375ca0199318e1ed72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 20V, Negative-QTOFsplash10-03di-0390000000-00a3ce15bb3eb85599112015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 40V, Negative-QTOFsplash10-014i-0910000000-f4f5c2c7d56cb15faa552015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 10V, Negative-QTOFsplash10-03di-0090000000-fa5c46c2572ef8a7bf102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 20V, Negative-QTOFsplash10-03di-0090000000-fa5c46c2572ef8a7bf102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 40V, Negative-QTOFsplash10-00lr-0900000000-3ce29982bbde6664bd6c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 10V, Positive-QTOFsplash10-03di-0090000000-7d2e191c18d3f0b0ca512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 20V, Positive-QTOFsplash10-03di-0090000000-7d2e191c18d3f0b0ca512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Urolithin B 40V, Positive-QTOFsplash10-03di-0190000000-62cb0bc11bbf77eca97b2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1038 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 1038 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030000
KNApSAcK IDC00053885
Chemspider ID4528673
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUrolithin B
METLIN IDNot Available
PubChem Compound5380406
PDB IDNot Available
ChEBI ID1050862
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1661681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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
Urolithin B → 3,4,5-trihydroxy-6-({6-oxo-6H-benzo[c]chromen-3-yl}oxy)oxane-2-carboxylic aciddetails