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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:38:02 UTC
Update Date2022-03-07 02:53:53 UTC
HMDB IDHMDB0033860
Secondary Accession Numbers
  • HMDB33860
Metabolite Identification
Common Name8-Hydroxydaidzein
Description8-Hydroxydaidzein 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, 8-hydroxydaidzein is considered to be a flavonoid. 8-Hydroxydaidzein has been detected, but not quantified in, pulses and soy beans (Glycine max). This could make 8-hydroxydaidzein a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 8-Hydroxydaidzein.
Structure
Data?1563862472
Synonyms
ValueSource
4'78-TrihydroxyisoflavoneChEMBL, HMDB
784'-TrihydroxyisoflavoneChEMBL, HMDB
4',7,8-TrihydroxyisoflavoneHMDB, MeSH
7,8,4'-TrihydroxyisoflavoneHMDB
7,8-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-oneHMDB
7,8-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
7,8-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ciHMDB
7,8-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-oneHMDB
7,8-Dihydroxy-3-(4-hydroxyphenyl)chromen-4-oneHMDB
NSC 678112HMDB
Chemical FormulaC15H10O5
Average Molecular Weight270.2369
Monoisotopic Molecular Weight270.05282343
IUPAC Name7,8-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Name8-hydroxydaidzein
CAS Registry Number75187-63-2
SMILES
OC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2O)C1=O
InChI Identifier
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-15-10(13(11)18)5-6-12(17)14(15)19/h1-7,16-17,19H
InChI KeyBMZFZTMWBCFKSS-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
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • 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
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point210 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP3.09ALOGPS
logP2.43ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.7ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.68 m³·mol⁻¹ChemAxon
Polarizability26.66 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]+162.10631661259
DarkChem[M-H]-161.6631661259
DeepCCS[M+H]+163.04930932474
DeepCCS[M-H]-160.69130932474
DeepCCS[M-2H]-193.57730932474
DeepCCS[M+Na]+169.14230932474
AllCCS[M+H]+160.932859911
AllCCS[M+H-H2O]+157.032859911
AllCCS[M+NH4]+164.532859911
AllCCS[M+Na]+165.632859911
AllCCS[M-H]-161.232859911
AllCCS[M+Na-2H]-160.432859911
AllCCS[M+HCOO]-159.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-HydroxydaidzeinOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2O)C1=O3905.9Standard polar33892256
8-HydroxydaidzeinOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2O)C1=O2848.3Standard non polar33892256
8-HydroxydaidzeinOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2O)C1=O2992.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hydroxydaidzein,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=COC3=C(O)C(O)=CC=C3C2=O)C=C13115.9Semi standard non polar33892256
8-Hydroxydaidzein,1TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1O3099.8Semi standard non polar33892256
8-Hydroxydaidzein,1TMS,isomer #3C[Si](C)(C)OC1=C(O)C=CC2=C1OC=C(C1=CC=C(O)C=C1)C2=O3051.4Semi standard non polar33892256
8-Hydroxydaidzein,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=COC3=C(O[Si](C)(C)C)C(O)=CC=C3C2=O)C=C13014.9Semi standard non polar33892256
8-Hydroxydaidzein,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2=COC3=C(O)C(O[Si](C)(C)C)=CC=C3C2=O)C=C13067.2Semi standard non polar33892256
8-Hydroxydaidzein,2TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1O[Si](C)(C)C2990.7Semi standard non polar33892256
8-Hydroxydaidzein,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2=COC3=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC=C3C2=O)C=C12914.9Semi standard non polar33892256
8-Hydroxydaidzein,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=C(O)C(O)=CC=C3C2=O)C=C13344.4Semi standard non polar33892256
8-Hydroxydaidzein,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1O3347.9Semi standard non polar33892256
8-Hydroxydaidzein,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=C1OC=C(C1=CC=C(O)C=C1)C2=O3300.2Semi standard non polar33892256
8-Hydroxydaidzein,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=C(O[Si](C)(C)C(C)(C)C)C(O)=CC=C3C2=O)C=C13524.8Semi standard non polar33892256
8-Hydroxydaidzein,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=C(O)C(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C13587.1Semi standard non polar33892256
8-Hydroxydaidzein,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1O[Si](C)(C)C(C)(C)C3511.4Semi standard non polar33892256
8-Hydroxydaidzein,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2=COC3=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C13659.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxydaidzein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-0490000000-f750d45a7e040a600f582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxydaidzein GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3132900000-4eeeec592a177168731f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxydaidzein 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 - 8-Hydroxydaidzein 10V, Positive-QTOFsplash10-00di-0090000000-5efad59f08e4178ef2982015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 20V, Positive-QTOFsplash10-00di-1090000000-afb26d4d2291c07e480f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 40V, Positive-QTOFsplash10-0uxs-9740000000-37fac6e953806b0565ab2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 10V, Negative-QTOFsplash10-014i-0090000000-21c0d38cb0290b77517d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 20V, Negative-QTOFsplash10-014i-0190000000-98ebbeb6735ac5d483d62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 40V, Negative-QTOFsplash10-052o-7930000000-942bf9b3a8d4d2bcdcef2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 10V, Positive-QTOFsplash10-00di-0090000000-ae6e5e86465295cd03322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 20V, Positive-QTOFsplash10-00di-0090000000-0dfe0b844ca2083b00a72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 40V, Positive-QTOFsplash10-0cdl-2950000000-38d3da8f1fe21643a1632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 10V, Negative-QTOFsplash10-014i-0090000000-4e65ba44fc45f7e80f5a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 20V, Negative-QTOFsplash10-014i-0090000000-733eeeabb31c76ef84432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxydaidzein 40V, Negative-QTOFsplash10-0a4i-0930000000-c68f0743ee061c350e4a2021-09-23Wishart 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 895 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012044
KNApSAcK IDC00009852
Chemspider ID4577542
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5466139
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.. .