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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2021-10-13 04:47:12 UTC
HMDB IDHMDB0005760
Secondary Accession Numbers
  • HMDB05760
Metabolite Identification
Common NameDihydrodaidzein
DescriptionDihydrodaidzein 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, dihydrodaidzein is considered to be a flavonoid. Dihydrodaidzein has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make dihydrodaidzein a potential biomarker for the consumption of these foods. Dihydrodaidzein 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 small amount of articles have been published on Dihydrodaidzein.
Structure
Data?1582752362
Synonyms
ValueSource
(+/-)-dihydrodaidzeinChEBI
2,3-Dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
7,4'-DihydroxyisoflavanoneChEBI
4',7-Dihydroxy-isoflavanoneHMDB
Chemical FormulaC15H12O4
Average Molecular Weight256.2534
Monoisotopic Molecular Weight256.073558872
IUPAC Name7-hydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name(+/-)-dihydrodaidzein
CAS Registry Number17238-05-0
SMILES
OC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O
InChI Identifier
InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2
InChI KeyJHYXBPPMXZIHKG-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
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Isoflavanone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ketone
  • Oxacycle
  • Ether
  • 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 Point250 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility873.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.77ALOGPS
logP2.38ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.78ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.7 m³·mol⁻¹ChemAxon
Polarizability25.76 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]+160.14431661259
DarkChem[M-H]-160.40531661259
DeepCCS[M+H]+160.83930932474
DeepCCS[M-H]-158.48130932474
DeepCCS[M-2H]-191.36730932474
DeepCCS[M+Na]+166.93230932474
AllCCS[M+H]+158.832859911
AllCCS[M+H-H2O]+154.932859911
AllCCS[M+NH4]+162.532859911
AllCCS[M+Na]+163.632859911
AllCCS[M-H]-161.032859911
AllCCS[M+Na-2H]-160.432859911
AllCCS[M+HCOO]-159.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydrodaidzeinOC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O3770.5Standard polar33892256
DihydrodaidzeinOC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O2665.8Standard non polar33892256
DihydrodaidzeinOC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O2752.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrodaidzein,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2=O)C=C12703.6Semi standard non polar33892256
Dihydrodaidzein,1TMS,isomer #2C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3)COC2=C12672.5Semi standard non polar33892256
Dihydrodaidzein,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C12726.2Semi standard non polar33892256
Dihydrodaidzein,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2=O)C=C12951.0Semi standard non polar33892256
Dihydrodaidzein,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3)COC2=C12935.3Semi standard non polar33892256
Dihydrodaidzein,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=C13229.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrodaidzein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-2790000000-5c32d81fea587727221d2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrodaidzein GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-7936000000-b483e2a442556fb427d92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrodaidzein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrodaidzein LC-ESI-QFT 17V, positive-QTOFsplash10-03di-0900000000-f3ddb99bf79f26ab077e2020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrodaidzein LC-ESI-IT 17V, positive-QTOFsplash10-03k9-0900000000-790a36fdcf35d00b97de2020-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 10V, Positive-QTOFsplash10-0a4i-0290000000-5103dee7bd918c7b6c9e2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 20V, Positive-QTOFsplash10-0a4r-0970000000-a12e6d9523183e1efc4a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 40V, Positive-QTOFsplash10-05ts-6910000000-83db00f15de1477dcc4f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 10V, Negative-QTOFsplash10-0a4i-0090000000-baed821bce01fea923c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 20V, Negative-QTOFsplash10-0a4i-0290000000-2fcebdf6ef2c3dc568ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 40V, Negative-QTOFsplash10-014l-7920000000-9009639f6e531f9f33d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 10V, Positive-QTOFsplash10-0a4i-0090000000-b46e3a63d530434294a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 20V, Positive-QTOFsplash10-0a4i-0590000000-dc00d36993e2435d676f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 40V, Positive-QTOFsplash10-0a6r-5920000000-4238c2fb09b7ca171b682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 10V, Negative-QTOFsplash10-0a4i-0090000000-82e226df9342cd67d7962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 20V, Negative-QTOFsplash10-0a4i-0290000000-99d6d002cfbacfc07cf12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrodaidzein 40V, Negative-QTOFsplash10-0j7r-1980000000-ce78cc93955eeefee01f2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 861 details
UrineDetected and Quantified0.114 +/- 0.03 (0.05 - 0.23) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0791 umol/mmol creatinineChildren (1-13 years old)FemaleNormal details
UrineDetected and Quantified0.0916 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.192 umol/mmol creatinineChildren (1-13 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0007 +/- 0.0003 (0.0001 - 0.002) umol/mmol creatinineAdult (>18 years old)BothSoy consumption (ileostomies) details
Associated Disorders and Diseases
Disease References
Ileostomy
  1. Walsh KR, Haak SJ, Bohn T, Tian Q, Schwartz SJ, Failla ML: Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies. Am J Clin Nutr. 2007 Apr;85(4):1050-6. [PubMed:17413104 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023752
KNApSAcK IDC00009533
Chemspider ID154076
KEGG Compound IDNot Available
BioCyc ID2-HYDROXY-23-DIHYDRODAIDZEIN
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound176907
PDB IDNot Available
ChEBI ID75842
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000469
Good Scents IDrw1134981
References
Synthesis ReferenceJain, Amolak C.; Nayyar, Naresh K. Synthesis of (±)-sativanone and (±)-dihydrodaidzein. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1987), 26B(2), 136-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Franke AA, Custer LJ, Wilkens LR, Le Marchand LL, Nomura AM, Goodman MT, Kolonel LN: Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):45-59. [PubMed:12270199 ]

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
Dihydrodaidzein → 3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic aciddetails
Dihydrodaidzein → 3,4,5-trihydroxy-6-[4-(7-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]oxane-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
Dihydrodaidzein → [4-(7-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenyl]oxidanesulfonic aciddetails