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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:08 UTC
Update Date2022-03-07 02:53:54 UTC
HMDB IDHMDB0033928
Secondary Accession Numbers
  • HMDB33928
Metabolite Identification
Common Name(±)-2'-Hydroxydihydrodaidzein
Description(±)-2'-Hydroxydihydrodaidzein, also known as 2',4',7-trihydroxyisoflavanone, 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. Thus, (±)-2'-hydroxydihydrodaidzein is considered to be a flavonoid (±)-2'-Hydroxydihydrodaidzein has been detected, but not quantified in, several different foods, such as millets (Panicum miliaceum), gooseberries (Ribes uva-crispa), black cabbages (Brassica oleracea var. viridis), pepper (capsicum), and dills (Anethum graveolens). This could make (±)-2'-hydroxydihydrodaidzein a potential biomarker for the consumption of these foods (±)-2'-Hydroxydihydrodaidzein 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 very few articles have been published on (±)-2'-Hydroxydihydrodaidzein.
Structure
Data?1563862483
Synonyms
ValueSource
2',4',7-TrihydroxyisoflavanoneChEBI
2'-HydroxydihydrodaidzeinChEBI
2'-Hydroxy-2,3-dihydrodaidzeinKegg
Chemical FormulaC15H12O5
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
IUPAC Name3-(2,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name2'-hydroxydihydrodaidzein
CAS Registry NumberNot Available
SMILES
OC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O
InChI Identifier
InChI=1S/C15H12O5/c16-8-1-3-10(13(18)5-8)12-7-20-14-6-9(17)2-4-11(14)15(12)19/h1-6,12,16-18H,7H2
InChI KeyWBOWBLGZAXVREM-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
  • Isoflavanone
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Chromone
  • 1-benzopyran
  • Chromane
  • Benzopyran
  • Resorcinol
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
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 Solubility0.24 g/LALOGPS
logP2.37ALOGPS
logP2.08ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.76ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.68 m³·mol⁻¹ChemAxon
Polarizability26.61 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]+164.32831661259
DarkChem[M-H]-161.71631661259
DeepCCS[M+H]+164.84830932474
DeepCCS[M-H]-162.4930932474
DeepCCS[M-2H]-195.37730932474
DeepCCS[M+Na]+170.94130932474
AllCCS[M+H]+162.532859911
AllCCS[M+H-H2O]+158.732859911
AllCCS[M+NH4]+166.032859911
AllCCS[M+Na]+167.132859911
AllCCS[M-H]-163.832859911
AllCCS[M+Na-2H]-163.232859911
AllCCS[M+HCOO]-162.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-2'-HydroxydihydrodaidzeinOC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O4090.9Standard polar33892256
(??)-2'-HydroxydihydrodaidzeinOC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O2848.9Standard non polar33892256
(??)-2'-HydroxydihydrodaidzeinOC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O2957.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-2'-Hydroxydihydrodaidzein,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2=O)C(O)=C12839.4Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC=C1C1COC2=CC(O)=CC=C2C1=O2788.9Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,1TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3O)COC2=C12848.9Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C(O)=C12854.3Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2=O)C(O[Si](C)(C)C)=C12812.5Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,2TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C)COC2=C12804.9Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)COC2=C12774.0Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2=O)C(O)=C13104.8Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1COC2=CC(O)=CC=C2C1=O3068.2Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3O)COC2=C13115.0Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C(O)=C13349.2Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2=O)C(O[Si](C)(C)C(C)(C)C)=C13292.1Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)COC2=C13304.1Semi standard non polar33892256
(??)-2'-Hydroxydihydrodaidzein,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)COC2=C13464.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2'-Hydroxydihydrodaidzein GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0980000000-e7979a463cd796295a822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2'-Hydroxydihydrodaidzein GC-MS (3 TMS) - 70eV, Positivesplash10-0g6r-5450900000-a800c4894c11409a36bb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 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'-Hydroxydihydrodaidzein 10V, Positive-QTOFsplash10-00di-0390000000-c38133f0021c27b3efd92015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 20V, Positive-QTOFsplash10-00dr-0960000000-1a0433299bbfb11330842015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 40V, Positive-QTOFsplash10-00ri-5910000000-cb74b5355f0b3ee29eff2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 10V, Positive-QTOFsplash10-00di-0390000000-c38133f0021c27b3efd92015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 20V, Positive-QTOFsplash10-00dr-0960000000-1a0433299bbfb11330842015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 40V, Positive-QTOFsplash10-00ri-5910000000-cb74b5355f0b3ee29eff2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 10V, Negative-QTOFsplash10-00di-0090000000-a0dd5832edb1bac1cd052015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 20V, Negative-QTOFsplash10-00di-0690000000-768c30539b246d1a2f812015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 40V, Negative-QTOFsplash10-0a4i-5910000000-b37100c6f50d013722e52015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 10V, Negative-QTOFsplash10-00di-0090000000-a0dd5832edb1bac1cd052015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 20V, Negative-QTOFsplash10-00di-0690000000-768c30539b246d1a2f812015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 40V, Negative-QTOFsplash10-0a4i-5910000000-b37100c6f50d013722e52015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 10V, Positive-QTOFsplash10-0229-0590000000-56bcd35a072be432516b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 20V, Positive-QTOFsplash10-00dr-0950000000-6f310fe2526ad75a613b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 40V, Positive-QTOFsplash10-00xr-3920000000-bee4c2a9a2cbe376257b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 10V, Negative-QTOFsplash10-0229-0590000000-233de55eb68ad799cca12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 20V, Negative-QTOFsplash10-00di-0290000000-0b2df6ad67c4ea806df02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2'-Hydroxydihydrodaidzein 40V, Negative-QTOFsplash10-014v-2980000000-ebf8792f139389ac217e2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB012128
KNApSAcK IDC00009535
Chemspider ID389058
KEGG Compound IDC03567
BioCyc ID2-HYDROXY-23-DIHYDRODAIDZEIN
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440047
PDB IDNot Available
ChEBI ID16035
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.. .