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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:47:20 UTC
Update Date2022-03-07 02:53:57 UTC
HMDB IDHMDB0034014
Secondary Accession Numbers
  • HMDB34014
Metabolite Identification
Common Name2'-Hydroxygenistein
Description2'-Hydroxygenistein 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, 2'-hydroxygenistein is considered to be a flavonoid. 2'-Hydroxygenistein has been detected, but not quantified in, several different foods, such as peanuts (Arachis hypogaea), corianders (Coriandrum sativum), fennels (Foeniculum vulgare), feijoas (Feijoa sellowiana), and groundcherries (Physalis). This could make 2'-hydroxygenistein a potential biomarker for the consumption of these foods. 2'-Hydroxygenistein 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 a significant number of articles have been published on 2'-Hydroxygenistein.
Structure
Data?1563862495
Synonyms
ValueSource
2',4',5,7-TetrahydroxyisoflavoneChEBI
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxychromen-4-oneChEBI
2',4',5,7-Tetrahydroxy-isoflavoneHMDB
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one, 9ciHMDB
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-oneHMDB
5,7,2',4'-Tetrahydroxy-isoflavoneHMDB
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
IUPAC Name3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
Traditional Name2'-hydroxygenistein
CAS Registry Number1156-78-1
SMILES
OC1=CC(O)=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C15H10O6/c16-7-1-2-9(11(18)3-7)10-6-21-13-5-8(17)4-12(19)14(13)15(10)20/h1-6,16-19H
InChI KeyGSSOWCUOWLMMRJ-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
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 - 273 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.59ALOGPS
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
Polarizability27.4 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]+164.70430932474
DeepCCS[M-H]-162.34630932474
DeepCCS[M-2H]-195.23230932474
DeepCCS[M+Na]+170.79730932474
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
2'-HydroxygenisteinOC1=CC(O)=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O4681.6Standard polar33892256
2'-HydroxygenisteinOC1=CC(O)=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O2843.6Standard non polar33892256
2'-HydroxygenisteinOC1=CC(O)=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O3073.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2'-Hydroxygenistein,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C(O)=C13100.8Semi standard non polar33892256
2'-Hydroxygenistein,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O3051.5Semi standard non polar33892256
2'-Hydroxygenistein,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3O)=COC2=C13119.8Semi standard non polar33892256
2'-Hydroxygenistein,1TMS,isomer #4C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1O)=CO23085.9Semi standard non polar33892256
2'-Hydroxygenistein,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C(O)=C13002.9Semi standard non polar33892256
2'-Hydroxygenistein,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C(O)=C12976.4Semi standard non polar33892256
2'-Hydroxygenistein,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C(O[Si](C)(C)C)=C13008.2Semi standard non polar33892256
2'-Hydroxygenistein,2TMS,isomer #4C[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C)=COC2=C12988.1Semi standard non polar33892256
2'-Hydroxygenistein,2TMS,isomer #5C[Si](C)(C)OC1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O2958.5Semi standard non polar33892256
2'-Hydroxygenistein,2TMS,isomer #6C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O)=COC2=C13004.6Semi standard non polar33892256
2'-Hydroxygenistein,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(O)=C12915.1Semi standard non polar33892256
2'-Hydroxygenistein,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C(O[Si](C)(C)C)=C12924.5Semi standard non polar33892256
2'-Hydroxygenistein,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C12914.9Semi standard non polar33892256
2'-Hydroxygenistein,3TMS,isomer #4C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C)=COC2=C12909.8Semi standard non polar33892256
2'-Hydroxygenistein,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C(O[Si](C)(C)C)=C12916.7Semi standard non polar33892256
2'-Hydroxygenistein,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C(O)=C13390.8Semi standard non polar33892256
2'-Hydroxygenistein,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O3339.2Semi standard non polar33892256
2'-Hydroxygenistein,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3O)=COC2=C13401.5Semi standard non polar33892256
2'-Hydroxygenistein,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(C1=CC=C(O)C=C1O)=CO23365.7Semi standard non polar33892256
2'-Hydroxygenistein,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(O)=C13599.0Semi standard non polar33892256
2'-Hydroxygenistein,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C13584.0Semi standard non polar33892256
2'-Hydroxygenistein,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13552.8Semi standard non polar33892256
2'-Hydroxygenistein,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C13559.5Semi standard non polar33892256
2'-Hydroxygenistein,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O3526.4Semi standard non polar33892256
2'-Hydroxygenistein,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O)=COC2=C13609.6Semi standard non polar33892256
2'-Hydroxygenistein,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O)=C13677.5Semi standard non polar33892256
2'-Hydroxygenistein,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13660.6Semi standard non polar33892256
2'-Hydroxygenistein,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13632.7Semi standard non polar33892256
2'-Hydroxygenistein,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C13630.1Semi standard non polar33892256
2'-Hydroxygenistein,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13801.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxygenistein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-0390000000-e070bd81e8144a8f57e12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxygenistein GC-MS (4 TMS) - 70eV, Positivesplash10-0mb9-3040190000-3575285d400806bec6c32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-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 - 2'-Hydroxygenistein 10V, Positive-QTOFsplash10-000i-0090000000-286fba4f31f8fb93eb492016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 20V, Positive-QTOFsplash10-000i-0090000000-4b594dca408dbed93fa32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 40V, Positive-QTOFsplash10-0uxr-3790000000-9e5519118c88d171aca92016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 10V, Negative-QTOFsplash10-000i-0090000000-839fbbc58c7b057175f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 20V, Negative-QTOFsplash10-000i-0090000000-e7cf04d0c70b706ebbd12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 40V, Negative-QTOFsplash10-0gc0-4980000000-c96bb8ee9097cc0923d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 10V, Negative-QTOFsplash10-000i-0090000000-3713e1ac18e8a67ad4542021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 20V, Negative-QTOFsplash10-000i-0090000000-5c8efa2c6b672fbcc81e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 40V, Negative-QTOFsplash10-00kf-0290000000-ab88b6e61b5ec5990b072021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 10V, Positive-QTOFsplash10-000i-0090000000-ad6070afb384abda8f3b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 20V, Positive-QTOFsplash10-000i-0090000000-ad6070afb384abda8f3b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxygenistein 40V, Positive-QTOFsplash10-00kg-1790000000-a0a3ffd1355cff7eab242021-09-24Wishart 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 IDFDB012251
KNApSAcK IDC00009453
Chemspider ID4445299
KEGG Compound IDC12134
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5282074
PDB IDNot Available
ChEBI ID70031
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
2'-Hydroxygenistein → 6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-3-yl)-3-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2'-Hydroxygenistein → 6-{[3-(2,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails