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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:43:44 UTC
Update Date2021-09-14 15:48:21 UTC
HMDB IDHMDB0037477
Secondary Accession Numbers
  • HMDB37477
Metabolite Identification
Common Name5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone
Description5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position. 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone has been detected, but not quantified in, herbs and spices. This could make 5,7-dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone.
Structure
Data?1563863037
Synonyms
ValueSource
3'-Hydroxy-3,9-dihydroeucominHMDB
Chemical FormulaC17H16O6
Average Molecular Weight316.3053
Monoisotopic Molecular Weight316.094688244
IUPAC Name5,7-dihydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,7-dihydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]-2,3-dihydro-1-benzopyran-4-one
CAS Registry Number107585-75-1
SMILES
COC1=C(O)C=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1
InChI Identifier
InChI=1S/C17H16O6/c1-22-14-3-2-9(5-12(14)19)4-10-8-23-15-7-11(18)6-13(20)16(15)17(10)21/h2-3,5-7,10,18-20H,4,8H2,1H3
InChI KeyWIBOONWRYQFYQJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassHomoisoflavonoids
Sub ClassHomoisoflavans
Direct ParentHomoisoflavanones
Alternative Parents
Substituents
  • Homoisoflavanone
  • Chromone
  • Methoxyphenol
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 - 142 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.076 g/LALOGPS
logP10(2.67) g/LALOGPS
logP10(3.01) g/LChemAxon
logS10(-3.6) g/LALOGPS
pKa (Strongest Acidic)7.92ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.74 m³·mol⁻¹ChemAxon
Polarizability31.15 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]+175.38731661259
DarkChem[M-H]-177.19331661259
DeepCCS[M+H]+178.09830932474
DeepCCS[M-H]-175.7430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanoneCOC1=C(O)C=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C14359.2Standard polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanoneCOC1=C(O)C=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C13081.3Standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanoneCOC1=C(O)C=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C13116.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,1TMS,isomer #1COC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C2927.6Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,1TMS,isomer #2COC1=CC=C(CC2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O2958.2Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,1TMS,isomer #3COC1=CC=C(CC2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O2983.6Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,2TMS,isomer #1COC1=CC=C(CC2COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C2892.7Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,2TMS,isomer #2COC1=CC=C(CC2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C2912.5Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,2TMS,isomer #3COC1=CC=C(CC2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O2939.7Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,3TMS,isomer #1COC1=CC=C(CC2COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C2911.3Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,1TBDMS,isomer #1COC1=CC=C(CC2COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3203.2Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,1TBDMS,isomer #2COC1=CC=C(CC2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O3229.6Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,1TBDMS,isomer #3COC1=CC=C(CC2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3246.6Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,2TBDMS,isomer #1COC1=CC=C(CC2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3400.2Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,2TBDMS,isomer #2COC1=CC=C(CC2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3417.0Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,2TBDMS,isomer #3COC1=CC=C(CC2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3441.5Semi standard non polar33892256
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone,3TBDMS,isomer #1COC1=CC=C(CC2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3594.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0963000000-2a1edeb0e952652a69c72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone GC-MS (3 TMS) - 70eV, Positivesplash10-02t9-3690770000-72b6a793545746ece3f72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 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 - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 10V, Positive-QTOFsplash10-014i-0529000000-87ceb5329045b17d4eb32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 20V, Positive-QTOFsplash10-0uxr-0922000000-eb96fe3c02f7711318e92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 40V, Positive-QTOFsplash10-0udr-2900000000-3f656bc4c9d7f1d5c32e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 10V, Negative-QTOFsplash10-014i-0219000000-89b2d6081555607352952015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 20V, Negative-QTOFsplash10-014i-0779000000-552904ca86e6820c16ff2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 40V, Negative-QTOFsplash10-0udi-1950000000-3737a5d2a6cb2056648e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 10V, Positive-QTOFsplash10-014i-0009000000-7195ac3ed96f1c08ffd12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 20V, Positive-QTOFsplash10-014i-0904000000-d21483a82a4cebbfd49d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 40V, Positive-QTOFsplash10-0gdl-1920000000-d425754d77f73bf0e1cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 10V, Negative-QTOFsplash10-014i-0009000000-a5811c0f9e3fc0f9d1742021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 20V, Negative-QTOFsplash10-016r-0449000000-8e63a594e26468dd50832021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone 40V, Negative-QTOFsplash10-03di-1943000000-2731db78ee0274f677cf2021-09-25Wishart 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 IDFDB016542
KNApSAcK IDC00056425
Chemspider ID358308
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound404571
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
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone → 3,4,5-trihydroxy-6-({7-hydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl}oxy)oxane-2-carboxylic aciddetails
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone → 3,4,5-trihydroxy-6-({5-hydroxy-3-[(3-hydroxy-4-methoxyphenyl)methyl]-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl}oxy)oxane-2-carboxylic aciddetails
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone → 6-{5-[(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)methyl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
5,7-Dihydroxy-3-(3-hydroxy-4-methoxybenzyl)-4-chromanone → {5-[(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)methyl]-2-methoxyphenyl}oxidanesulfonic aciddetails