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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:56:01 UTC
Update Date2022-03-07 02:54:00 UTC
HMDB IDHMDB0034138
Secondary Accession Numbers
  • HMDB34138
Metabolite Identification
Common NameRepensol
DescriptionRepensol 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, repensol is considered to be a flavonoid lipid molecule. Repensol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, repensol has been detected, but not quantified in, a few different foods, such as green vegetables, herbs and spices, and tea. This could make repensol a potential biomarker for the consumption of these foods.
Structure
Data?1563862517
Synonyms
ValueSource
3,7,9-Trihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ciHMDB
7,10,12-TrihydroxycoumestanHMDB
Repensol3,7,9-trihydroxycoumestanHMDB
Chemical FormulaC15H8O6
Average Molecular Weight284.2204
Monoisotopic Molecular Weight284.032087988
IUPAC Name5,12,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Name5,12,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
CAS Registry Number33280-69-2
SMILES
OC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O2
InChI Identifier
InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)21-15(19)13-12-9(18)3-7(17)5-11(12)20-14(8)13/h1-5,16-18H
InChI KeyCFUAZBGEKBTCSH-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
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point346 - 348 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP2.58ALOGPS
logP2.09ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)7.07ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.13 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.6 m³·mol⁻¹ChemAxon
Polarizability27.24 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]+161.7731661259
DarkChem[M-H]-164.11331661259
DeepCCS[M+H]+167.5130932474
DeepCCS[M-H]-165.15230932474
DeepCCS[M-2H]-198.31930932474
DeepCCS[M+Na]+173.60330932474
AllCCS[M+H]+163.032859911
AllCCS[M+H-H2O]+159.232859911
AllCCS[M+NH4]+166.532859911
AllCCS[M+Na]+167.532859911
AllCCS[M-H]-163.332859911
AllCCS[M+Na-2H]-162.232859911
AllCCS[M+HCOO]-161.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RepensolOC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O24598.2Standard polar33892256
RepensolOC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O22534.9Standard non polar33892256
RepensolOC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O23159.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Repensol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC(O)=C213165.9Semi standard non polar33892256
Repensol,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C1=C(O2)C2=CC=C(O)C=C2OC1=O3113.4Semi standard non polar33892256
Repensol,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C213134.2Semi standard non polar33892256
Repensol,2TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC(O)=C213240.0Semi standard non polar33892256
Repensol,2TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC(O[Si](C)(C)C)=C213175.4Semi standard non polar33892256
Repensol,2TMS,isomer #3C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C213147.2Semi standard non polar33892256
Repensol,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C213299.6Semi standard non polar33892256
Repensol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC(O)=C213383.1Semi standard non polar33892256
Repensol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C1=C(O2)C2=CC=C(O)C=C2OC1=O3314.4Semi standard non polar33892256
Repensol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C213350.7Semi standard non polar33892256
Repensol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C213679.9Semi standard non polar33892256
Repensol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C213615.9Semi standard non polar33892256
Repensol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C213579.2Semi standard non polar33892256
Repensol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C213947.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Repensol GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-0090000000-02879d089d9526293c3c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Repensol GC-MS (3 TMS) - 70eV, Positivesplash10-00bi-3001900000-447c045c9fbf2a9b6dab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Repensol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Repensol 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 - Repensol 10V, Positive-QTOFsplash10-000i-0090000000-9be28a959ef0b37d8bc82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 20V, Positive-QTOFsplash10-000i-0090000000-0e33bfa58857dae13e6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 40V, Positive-QTOFsplash10-014l-1190000000-a5b6bb1b5f294453f38d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 10V, Negative-QTOFsplash10-001i-0090000000-91aee8e36c50140836452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 20V, Negative-QTOFsplash10-001i-0090000000-d1f47f392c533df773772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 40V, Negative-QTOFsplash10-000i-0290000000-4a1c98a40450b17a81e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 10V, Positive-QTOFsplash10-000i-0090000000-3896d645ce486a1e32ca2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 20V, Positive-QTOFsplash10-000i-0090000000-3896d645ce486a1e32ca2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 40V, Positive-QTOFsplash10-0a4l-0090000000-86d2b3afdb851de8274a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 10V, Negative-QTOFsplash10-001i-0090000000-279002154c712db975df2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 20V, Negative-QTOFsplash10-001i-0090000000-279002154c712db975df2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Repensol 40V, Negative-QTOFsplash10-03gi-0090000000-8b7db004d7c35df3ff902021-09-25Wishart 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 IDFDB012413
KNApSAcK IDC00009758
Chemspider ID24843113
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257533
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
Repensol → 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-12-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Repensol → 6-({5,12-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Repensol → 6-({12,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails