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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:34:36 UTC
Update Date2022-03-07 02:57:07 UTC
HMDB IDHMDB0041658
Secondary Accession Numbers
  • HMDB41658
Metabolite Identification
Common Name3'-Hydroxygenistein
Description3'-Hydroxygenistein, also known as isoluteolin or norsantal, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 3'-hydroxygenistein is considered to be a flavonoid. 3'-Hydroxygenistein is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3'-Hydroxygenistein.
Structure
Data?1563863688
Synonyms
ValueSource
3',4',5,7-TetrahydroxyisoflavoneChEBI
5,7-Dihydroxy-3-(3,4-dihydroxyphenyl)-4-1H-benzopyran-4-oneChEBI
IsoluteolinChEBI
NorsantalChEBI
SantolChEBI
3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-oneHMDB
3'-HydroxygenisteinChEBI
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
IUPAC Name3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Traditional Namequercitin
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C15H10O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-6,16-19H
InChI KeyIOYHCQBYQJQBSK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflav-2-enes
Direct ParentIsoflavones
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.14 g/LALOGPS
logP2.64ALOGPS
logP2.77ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.6ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.66 m³·mol⁻¹ChemAxon
Polarizability27.53 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
DeepCCS[M+H]+167.67330932474
DeepCCS[M-H]-165.31530932474
DeepCCS[M-2H]-198.80230932474
DeepCCS[M+Na]+174.02930932474
AllCCS[M+H]+164.532859911
AllCCS[M+H-H2O]+160.732859911
AllCCS[M+NH4]+168.032859911
AllCCS[M+Na]+169.032859911
AllCCS[M-H]-164.132859911
AllCCS[M+Na-2H]-163.332859911
AllCCS[M+HCOO]-162.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3'-HydroxygenisteinOC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C14464.2Standard polar33892256
3'-HydroxygenisteinOC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C12974.2Standard non polar33892256
3'-HydroxygenisteinOC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C13085.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3'-Hydroxygenistein,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O)=C3)=COC2=C13243.6Semi standard non polar33892256
3'-Hydroxygenistein,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C(O)=C1)=CO23192.3Semi standard non polar33892256
3'-Hydroxygenistein,1TMS,isomer #3C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O3244.4Semi standard non polar33892256
3'-Hydroxygenistein,1TMS,isomer #4C[Si](C)(C)OC1=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=CC=C1O3237.1Semi standard non polar33892256
3'-Hydroxygenistein,2TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C(O)=C3)=COC2=C13099.1Semi standard non polar33892256
3'-Hydroxygenistein,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=COC2=C13152.0Semi standard non polar33892256
3'-Hydroxygenistein,2TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=COC2=C13115.0Semi standard non polar33892256
3'-Hydroxygenistein,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O3084.5Semi standard non polar33892256
3'-Hydroxygenistein,2TMS,isomer #5C[Si](C)(C)OC1=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O3057.9Semi standard non polar33892256
3'-Hydroxygenistein,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C3041.0Semi standard non polar33892256
3'-Hydroxygenistein,3TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=COC2=C13050.7Semi standard non polar33892256
3'-Hydroxygenistein,3TMS,isomer #2C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=COC2=C13017.4Semi standard non polar33892256
3'-Hydroxygenistein,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=C12995.6Semi standard non polar33892256
3'-Hydroxygenistein,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C2954.9Semi standard non polar33892256
3'-Hydroxygenistein,4TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=COC2=C13002.7Semi standard non polar33892256
3'-Hydroxygenistein,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C(O)=C3)=COC2=C13515.2Semi standard non polar33892256
3'-Hydroxygenistein,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C(O)=C1)=CO23458.6Semi standard non polar33892256
3'-Hydroxygenistein,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O3521.7Semi standard non polar33892256
3'-Hydroxygenistein,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(C2=COC3=CC(O)=CC(O)=C3C2=O)=CC=C1O3496.9Semi standard non polar33892256
3'-Hydroxygenistein,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C(O)=C3)=COC2=C13693.7Semi standard non polar33892256
3'-Hydroxygenistein,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=C13728.9Semi standard non polar33892256
3'-Hydroxygenistein,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=C13691.7Semi standard non polar33892256
3'-Hydroxygenistein,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3685.7Semi standard non polar33892256
3'-Hydroxygenistein,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O3651.3Semi standard non polar33892256
3'-Hydroxygenistein,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3679.8Semi standard non polar33892256
3'-Hydroxygenistein,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=COC2=C13827.5Semi standard non polar33892256
3'-Hydroxygenistein,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=COC2=C13801.1Semi standard non polar33892256
3'-Hydroxygenistein,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=C13785.7Semi standard non polar33892256
3'-Hydroxygenistein,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3736.7Semi standard non polar33892256
3'-Hydroxygenistein,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=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=C13920.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3'-Hydroxygenistein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0390000000-360652882f44b694b8a22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-Hydroxygenistein GC-MS (4 TMS) - 70eV, Positivesplash10-0zmj-1050090000-909e736154fd67b61eee2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3'-Hydroxygenistein 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'-Hydroxygenistein 10V, Positive-QTOFsplash10-000i-0090000000-d8988c733e9e4df4bfba2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 20V, Positive-QTOFsplash10-052r-0190000000-347483b589c525c2fcdd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 40V, Positive-QTOFsplash10-0561-8970000000-3d0b46ec82c93f615c732017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 10V, Negative-QTOFsplash10-000i-0090000000-9f7fc9fd5ad08a4e2ad92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 20V, Negative-QTOFsplash10-000i-0290000000-459546584a2daa02d9ac2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 40V, Negative-QTOFsplash10-0ar0-0890000000-05cce6d7cfefddb814542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 10V, Positive-QTOFsplash10-000i-0090000000-ad6070afb384abda8f3b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 20V, Positive-QTOFsplash10-000i-0090000000-f1461cca4e9ac5b2e7f42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 40V, Positive-QTOFsplash10-004j-0490000000-3ed95cff32fb341dc5012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 10V, Negative-QTOFsplash10-000i-0090000000-3713e1ac18e8a67ad4542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 20V, Negative-QTOFsplash10-000i-0090000000-ed604628cd07f974a5b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3'-Hydroxygenistein 40V, Negative-QTOFsplash10-0udi-1090000000-c3721d2c48ba328d8a202021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 903 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029814
KNApSAcK IDC00002554
Chemspider ID4445113
KEGG Compound IDC10510
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOrobol
METLIN IDNot Available
PubChem Compound5281801
PDB IDNot Available
ChEBI ID69437
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'-Hydroxygenistein → 5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-chromen-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'-Hydroxygenistein → 6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3'-Hydroxygenistein → 6-{[3-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-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'-Hydroxygenistein → [5-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-2-hydroxyphenyl]oxidanesulfonic aciddetails