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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-04-03 14:10:31 UTC
Update Date2020-11-09 23:29:18 UTC
HMDB IDHMDB0013679
Secondary Accession Numbers
  • HMDB13679
Metabolite Identification
Common NameBergaptol
DescriptionBergaptol, also known as 5-hydroxypsoralen, belongs to the class of organic compounds known as 5-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C5 position of the psoralen group. Bergaptol has been detected, but not quantified in, several different foods, such as spinaches (Spinacia oleracea), sugar apples (Annona squamosa), biscuit, chicory leaves (Cichorium intybus var. foliosum), and docks (Rumex). This could make bergaptol a potential biomarker for the consumption of these foods. Bergaptol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Bergaptol.
Structure
Data?1582753142
Synonyms
ValueSource
5-HydroxyfuranocoumarinChEBI
5-HydroxypsoralenChEBI
4-Hydroxy-7H-furo(3,2-g)chromen-7-oneMeSH
4-Hydroxy-7H-furo[3,2-g]chromen-7-oneHMDB
4-Hydroxy-7H-furo[3,2-g]chromen-7-one (acd/name 4.0)HMDB
5-HYDROXY-psoralinHMDB
BergaptolsHMDB
Chemical FormulaC11H6O4
Average Molecular Weight202.165
Monoisotopic Molecular Weight202.026608673
IUPAC Name4-hydroxy-7H-furo[3,2-g]chromen-7-one
Traditional Namebergaptol
CAS Registry Number486-60-2
SMILES
OC1=C2C=CC(=O)OC2=CC2=C1C=CO2
InChI Identifier
InChI=1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
InChI KeyGIJHDGJRTUSBJR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5-hydroxypsoralens. These are psoralens containing a hydroxyl group attached at the C5 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent5-hydroxypsoralens
Alternative Parents
Substituents
  • 5-hydroxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.89 g/LALOGPS
logP1.86ALOGPS
logP1.64ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.45ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.67 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity52.37 m³·mol⁻¹ChemAxon
Polarizability18.94 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]+144.54931661259
DarkChem[M-H]-142.06931661259
DeepCCS[M+H]+139.53830932474
DeepCCS[M-H]-137.14230932474
DeepCCS[M-2H]-171.87530932474
DeepCCS[M+Na]+146.1330932474
AllCCS[M+H]+141.732859911
AllCCS[M+H-H2O]+137.332859911
AllCCS[M+NH4]+145.932859911
AllCCS[M+Na]+147.132859911
AllCCS[M-H]-141.232859911
AllCCS[M+Na-2H]-140.832859911
AllCCS[M+HCOO]-140.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BergaptolOC1=C2C=CC(=O)OC2=CC2=C1C=CO23002.3Standard polar33892256
BergaptolOC1=C2C=CC(=O)OC2=CC2=C1C=CO21968.2Standard non polar33892256
BergaptolOC1=C2C=CC(=O)OC2=CC2=C1C=CO22052.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bergaptol,1TMS,isomer #1C[Si](C)(C)OC1=C2C=COC2=CC2=C1C=CC(=O)O22183.9Semi standard non polar33892256
Bergaptol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C2C=COC2=CC2=C1C=CC(=O)O22456.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bergaptol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1910000000-e6a47789c6cb25ff3a462017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bergaptol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4090000000-566be005cc2959d866522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bergaptol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergaptol LC-ESI-qTof , Positive-QTOFsplash10-0002-0910000000-cc054eaed6fc83b4a27a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergaptol , positive-QTOFsplash10-0002-0910000000-cc054eaed6fc83b4a27a2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 10V, Positive-QTOFsplash10-0udi-0190000000-ac460f53d5cb80eb50442015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 20V, Positive-QTOFsplash10-0udi-0490000000-b86689b17be620c214e62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 40V, Positive-QTOFsplash10-03dr-1900000000-6193deca8502dc5323072015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 10V, Negative-QTOFsplash10-0udi-0190000000-f8c060c4143f0fd9068c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 20V, Negative-QTOFsplash10-0udi-0490000000-f83b2cbc9d5dea16671f2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 40V, Negative-QTOFsplash10-053r-1900000000-6a70dde5da85af79bd842015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 10V, Negative-QTOFsplash10-0udi-0090000000-6f70ceb2368baddf4f402021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 20V, Negative-QTOFsplash10-0udi-0090000000-6f70ceb2368baddf4f402021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 40V, Negative-QTOFsplash10-0ab9-0920000000-3f79d1ece069a20ce05b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 10V, Positive-QTOFsplash10-0udi-0090000000-2e5a86e101fa40f235c92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 20V, Positive-QTOFsplash10-0udi-0090000000-2e5a86e101fa40f235c92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergaptol 40V, Positive-QTOFsplash10-0a6r-0910000000-3e2fa866225a62b552632021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002543
KNApSAcK IDC00000581
Chemspider ID4444066
KEGG Compound IDC00758
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBergaptol
METLIN IDNot Available
PubChem Compound5280371
PDB IDNot Available
ChEBI ID17377
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 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
Bergaptol → 3,4,5-trihydroxy-6-({7-oxo-7H-furo[3,2-g]chromen-4-yl}oxy)oxane-2-carboxylic aciddetails