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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:34:13 UTC
Update Date2022-03-07 02:57:07 UTC
HMDB IDHMDB0041651
Secondary Accession Numbers
  • HMDB41651
Metabolite Identification
Common Name3',4',5,7-Tetrahydroxyisoflavanone
Description3',4',5,7-Tetrahydroxyisoflavanone belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Based on a literature review very few articles have been published on 3',4',5,7-Tetrahydroxyisoflavanone.
Structure
Data?1563863687
SynonymsNot Available
Chemical FormulaC15H12O6
Average Molecular Weight288.2522
Monoisotopic Molecular Weight288.063388116
IUPAC Name3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
OC1=CC(O)=C2C(=O)C(COC2=C1)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H12O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-5,9,16-19H,6H2
InChI KeyDYLLIDCIKLUGBZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct ParentIsoflavanones
Alternative Parents
Substituents
  • Isoflavanol
  • Isoflavanone
  • Hydroxyisoflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Catechol
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP2.1ALOGPS
logP2.42ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.89ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.66 m³·mol⁻¹ChemAxon
Polarizability27.44 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]+167.17131661259
DarkChem[M-H]-163.47731661259
DeepCCS[M+H]+168.55230932474
DeepCCS[M-H]-166.19430932474
DeepCCS[M-2H]-199.62230932474
DeepCCS[M+Na]+174.84930932474
AllCCS[M+H]+165.732859911
AllCCS[M+H-H2O]+162.032859911
AllCCS[M+NH4]+169.132859911
AllCCS[M+Na]+170.132859911
AllCCS[M-H]-165.932859911
AllCCS[M+Na-2H]-165.332859911
AllCCS[M+HCOO]-164.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3',4',5,7-TetrahydroxyisoflavanoneOC1=CC(O)=C2C(=O)C(COC2=C1)C1=CC(O)=C(O)C=C13927.5Standard polar33892256
3',4',5,7-TetrahydroxyisoflavanoneOC1=CC(O)=C2C(=O)C(COC2=C1)C1=CC(O)=C(O)C=C13030.8Standard non polar33892256
3',4',5,7-TetrahydroxyisoflavanoneOC1=CC(O)=C2C(=O)C(COC2=C1)C1=CC(O)=C(O)C=C12965.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3',4',5,7-Tetrahydroxyisoflavanone,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O)=C3)COC2=C13000.9Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C(O)=C1)CO23008.4Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,1TMS,isomer #3C[Si](C)(C)OC1=CC(C2COC3=CC(O)=CC(O)=C3C2=O)=CC=C1O3013.2Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,1TMS,isomer #4C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C=C1O3013.2Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O)C(O)=C3)CO2)C(O[Si](C)(C)C)=C12914.3Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)COC2=C12957.1Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)COC2=C12955.9Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O2965.3Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TMS,isomer #5C[Si](C)(C)OC1=CC(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O2983.5Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C2925.8Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)CO2)C(O[Si](C)(C)C)=C12912.2Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,3TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)CO2)C(O[Si](C)(C)C)=C12893.2Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,3TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)COC2=C12861.9Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C2878.9Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,4TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)CO2)C(O[Si](C)(C)C)=C12893.8Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O)=C3)COC2=C13269.7Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C(O)=C1)CO23274.7Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(C2COC3=CC(O)=CC(O)=C3C2=O)=CC=C1O3289.0Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C=C1O3290.3Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O)C(O)=C3)CO2)C(O[Si](C)(C)C(C)(C)C)=C13454.1Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)COC2=C13483.5Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)COC2=C13462.9Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3483.9Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O3503.2Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3464.0Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)CO2)C(O[Si](C)(C)C(C)(C)C)=C13629.6Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)CO2)C(O[Si](C)(C)C(C)(C)C)=C13610.2Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)COC2=C13597.5Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3610.4Semi standard non polar33892256
3',4',5,7-Tetrahydroxyisoflavanone,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)CO2)C(O[Si](C)(C)C(C)(C)C)=C13748.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-074i-0970000000-b86a48cf4ef8b81ea60d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone GC-MS (4 TMS) - 70eV, Positivesplash10-0ik9-2550090000-b29a30265828b836beeb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 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 - 3',4',5,7-Tetrahydroxyisoflavanone 10V, Positive-QTOFsplash10-000i-0490000000-cacfecf082999edbcc7c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 20V, Positive-QTOFsplash10-0kmr-0960000000-36ed6acdfc71b92c6ac42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 40V, Positive-QTOFsplash10-0ugr-5900000000-24dcd2d82a20cb3e9f122015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 10V, Negative-QTOFsplash10-000i-0090000000-6d81a700ba5b6dd1cd022015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 20V, Negative-QTOFsplash10-002r-0690000000-2867d825aac45e8d14bb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 40V, Negative-QTOFsplash10-0pbi-1930000000-c74734aed47c41ac153b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 10V, Positive-QTOFsplash10-000i-0090000000-c82a5662904c9453e8dd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 20V, Positive-QTOFsplash10-000i-0790000000-7a87efb876ab5a2c47c32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 40V, Positive-QTOFsplash10-0gi0-2930000000-9d30daf8965c31aaae0c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 10V, Negative-QTOFsplash10-000i-0090000000-8718937f43d1bf07c8192021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 20V, Negative-QTOFsplash10-000i-0290000000-a38207bb5cb3e5e93e022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3',4',5,7-Tetrahydroxyisoflavanone 40V, Negative-QTOFsplash10-014i-2590000000-83e9b2ce280c805c8a732021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 900 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029806
KNApSAcK IDNot Available
Chemspider ID35015212
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53785840
PDB IDNot Available
ChEBI ID174746
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. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
3',4',5,7-Tetrahydroxyisoflavanone → 5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-onedetails
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
3',4',5,7-Tetrahydroxyisoflavanone → 6-[5-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3',4',5,7-Tetrahydroxyisoflavanone → 6-{[3-(3,4-dihydroxyphenyl)-7-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3',4',5,7-Tetrahydroxyisoflavanone → 6-{[3-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3',4',5,7-Tetrahydroxyisoflavanone → 6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)-2-hydroxyphenoxy]-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
3',4',5,7-Tetrahydroxyisoflavanone → [5-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)-2-hydroxyphenyl]oxidanesulfonic aciddetails