You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:46:00 UTC
Update Date2021-09-14 15:44:45 UTC
HMDB IDHMDB0033991
Secondary Accession Numbers
  • HMDB33991
Metabolite Identification
Common NameDaidzin
DescriptionDaidzin, also known as daidzoside, belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Thus, daidzin is considered to be a flavonoid. Daidzin is a bitter tasting compound. Daidzin is found, on average, in the highest concentration within a few different foods, such as soy beans (Glycine max), yogurt, and soy yogurt and in a lower concentration in other soy product, soy milk, and miso. Daidzin has also been detected, but not quantified in, several different foods, such as black radishes (Raphanus sativus var. niger), allspices (Pimenta dioica), olives (Olea europaea), teas (Camellia sinensis), and radish (var.). This could make daidzin a potential biomarker for the consumption of these foods. Daidzin 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 Daidzin.
Structure
Data?1563862491
Synonyms
ValueSource
Daidzein 7-glucosideChEBI
Daidzein 7-O-glucosideChEBI
DaidzosideChEBI
7-O-Glucosyl-4'-hydroxyisoflavoneMeSH
4',7-Dihydroxyisoflavone 7-O-b-D-glucopyranosideHMDB
Daidzein 7-O-beta-D-glucopyranosideHMDB
Daidzein 7-O-beta-D-glucosideHMDB
DZNHMDB
DaidzinChEBI
Daidzein 7-O-b-D-glucosideGenerator, HMDB
Daidzein 7-O-β-D-glucosideGenerator, HMDB
Chemical FormulaC21H20O9
Average Molecular Weight416.382
Monoisotopic Molecular Weight416.110732224
IUPAC Name3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Namedaidzin
CAS Registry Number552-66-9
SMILES
OC[C@H]1O[C@@H](OC2=CC3=C(C=C2)C(=O)C(=CO3)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1
InChI KeyKYQZWONCHDNPDP-QNDFHXLGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavonoid O-glycosides
Direct ParentIsoflavonoid O-glycosides
Alternative Parents
Substituents
  • Isoflavonoid o-glycoside
  • Isoflavonoid-7-o-glycoside
  • Isoflavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point233 - 235 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.66 g/LALOGPS
logP0.71ALOGPS
logP0.46ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.85 m³·mol⁻¹ChemAxon
Polarizability41.25 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available194.92131661259
DarkChem[M-H]-PredictedNot Available192.66831661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Daidzin,1TMS,#13967.254https://arxiv.org/abs/1905.12712
Daidzin,1TMS,#23992.527https://arxiv.org/abs/1905.12712
Daidzin,1TMS,#33987.7898https://arxiv.org/abs/1905.12712
Daidzin,1TMS,#43975.184https://arxiv.org/abs/1905.12712
Daidzin,1TMS,#53961.7861https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#13859.4385https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#23843.009https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#33828.4175https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#43856.1582https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#53860.037https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#63877.3564https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#73874.4094https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#83836.939https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#93865.0276https://arxiv.org/abs/1905.12712
Daidzin,2TMS,#103833.1143https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#13791.584https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#23785.217https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#33796.3765https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#43780.899https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#53783.4106https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#63781.8232https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#73795.1294https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#83800.8184https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#93814.8445https://arxiv.org/abs/1905.12712
Daidzin,3TMS,#103787.6501https://arxiv.org/abs/1905.12712
Daidzin,4TMS,#13772.8154https://arxiv.org/abs/1905.12712
Daidzin,4TMS,#23773.3706https://arxiv.org/abs/1905.12712
Daidzin,4TMS,#33778.2415https://arxiv.org/abs/1905.12712
Daidzin,4TMS,#43783.3794https://arxiv.org/abs/1905.12712
Daidzin,4TMS,#53800.64https://arxiv.org/abs/1905.12712
Daidzin,5TMS,#13804.0698https://arxiv.org/abs/1905.12712
Daidzin,1TBDMS,#14233.6426https://arxiv.org/abs/1905.12712
Daidzin,1TBDMS,#24238.135https://arxiv.org/abs/1905.12712
Daidzin,1TBDMS,#34240.187https://arxiv.org/abs/1905.12712
Daidzin,1TBDMS,#44218.0537https://arxiv.org/abs/1905.12712
Daidzin,1TBDMS,#54217.531https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#14417.652https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#24375.3555https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#34345.934https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#44379.804https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#54407.0654https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#64423.5933https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#74416.1025https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#84335.39https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#94362.2266https://arxiv.org/abs/1905.12712
Daidzin,2TBDMS,#104331.448https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#14578.746https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#24567.685https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#34578.5947https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#44486.5454https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#54509.8154https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#64488.904https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#74566.122https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#84582.3125https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#94588.929https://arxiv.org/abs/1905.12712
Daidzin,3TBDMS,#104489.539https://arxiv.org/abs/1905.12712
Daidzin,4TBDMS,#14682.174https://arxiv.org/abs/1905.12712
Daidzin,4TBDMS,#24707.2573https://arxiv.org/abs/1905.12712
Daidzin,4TBDMS,#34686.7075https://arxiv.org/abs/1905.12712
Daidzin,4TBDMS,#44646.4785https://arxiv.org/abs/1905.12712
Daidzin,4TBDMS,#54682.1074https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f72-5619000000-9a00dd3afb417b948c0d2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-3614129000-e673b080216b7c8416582017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0000092000-84a513c4afef1602030f2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03di-0000092000-84a513c4afef1602030f2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-03di-0000900000-a8a90b48831795fcef5b2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-03di-0000900000-a8a90b48831795fcef5b2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0w29-0090800000-71336b3ac56112e899652017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0w29-0090800000-71336b3ac56112e899652017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0090100000-a3ff46535f112a06438e2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0090000000-806672a9fe6ab0e8821b2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-03di-0000900000-a8a90b48831795fcef5b2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0090300000-0e1086947a1b1fb0fc9c2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0w29-0090800000-71336b3ac56112e899652017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0090000000-3c95cabcacf790fe32be2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uxr-0190300000-7c009a9b8fd016988c202017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090300000-87d938e172f23b8f92662017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090101010-00cce9f1d03944bfc8392017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-f372e3204e88dfa0fac62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0089-2970000000-19bb9d5854402bda73862017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0190200000-21f48ac2697d0d52ecd22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090000000-65cde820e99b7330181c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090000000-02d2e6531c1f5306a9822017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090005000-e1a64aa9987c014a34792017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090005100-ebd792ec79716bac22ca2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0020900000-903830e8fc3941dbcc842021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-0291700000-1e92e4b123fc0c2fb01c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0290000000-9b77f7d15a867f015dcc2021-09-20View 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 IDDB02115
Phenol Explorer Compound ID403
FooDB IDFDB012225
KNApSAcK IDC00002518
Chemspider ID97088
KEGG Compound IDC10216
BioCyc IDCPD-3424
BiGG IDNot Available
Wikipedia LinkDaidzin
METLIN IDNot Available
PubChem Compound107971
PDB IDDZN
ChEBI ID42202
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kato K, Takahashi S, Cui L, Toda T, Suzuki S, Futakuchi M, Sugiura S, Shirai T: Suppressive effects of dietary genistin and daidzin on rat prostate carcinogenesis. Jpn J Cancer Res. 2000 Aug;91(8):786-91. [PubMed:10965018 ]
  2. Choo MK, Park EK, Yoon HK, Kim DH: Antithrombotic and antiallergic activities of daidzein, a metabolite of puerarin and daidzin produced by human intestinal microflora. Biol Pharm Bull. 2002 Oct;25(10):1328-32. [PubMed:12392089 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5
References
  1. Perez M, Real R, Mendoza G, Merino G, Prieto JG, Alvarez AI: Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones. J Vet Pharmacol Ther. 2009 Oct;32(5):498-502. doi: 10.1111/j.1365-2885.2008.01050.x. [PubMed:19754918 ]