AFCDB: Daidzin (FDB012225)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:03 UTC

Update date

2019-11-26 03:06:26 UTC

Primary ID

FDB012225

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Daidzin

Description

Daidzin, 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 miso, other soy product, and soy milk. Daidzin has also been detected, but not quantified in, several different foods, such as fox grapes (Vitis labrusca), green zucchinis (Cucurbita pepo var. cylindrica), fruits, globe artichokes (Cynara scolymus), and canola. This could make daidzin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Daidzin.

CAS Number

552-66-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	0.71	ALOGPS
logP	0.46	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	101.85 m³·mol⁻¹	ChemAxon
Polarizability	41.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H20O9

IUPAC name

3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

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 Key

KYQZWONCHDNPDP-QNDFHXLGSA-N

Isomeric 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

Average Molecular Weight

416.382

Monoisotopic Molecular Weight

416.110732224

Classification

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:42202 )
monosaccharide derivative (CHEBI:42202 )
hydroxyisoflavone (CHEBI:42202 )
glycosyloxyisoflavone (CHEBI:42202 )
isoflavones (C10216 )
Isoflavonoids (C10216 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Drug

Pharmaceutical industry:

Antineoplastic agent:

Anticancer agent

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 60.58%; H 4.84%; O 34.58%	DFC
Melting Point	Mp 233-235°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -36.4 (0.02M KOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Daidzin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f72-5619000000-9a00dd3afb417b948c0d	Spectrum
Predicted GC-MS	Daidzin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-3614129000-e673b080216b7c841658	Spectrum
Predicted GC-MS	Daidzin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-03di-0000092000-84a513c4afef1602030f	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-03di-0000092000-84a513c4afef1602030f	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-03di-0000900000-a8a90b48831795fcef5b	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-03di-0000900000-a8a90b48831795fcef5b	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0w29-0090800000-71336b3ac56112e89965	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0w29-0090800000-71336b3ac56112e89965	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0udi-0090100000-a3ff46535f112a06438e	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-0udi-0090000000-806672a9fe6ab0e8821b	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-03di-0000900000-a8a90b48831795fcef5b	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0090300000-0e1086947a1b1fb0fc9c	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0w29-0090800000-71336b3ac56112e89965	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0udi-0090000000-3c95cabcacf790fe32be	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0uxr-0190300000-7c009a9b8fd016988c20	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090300000-87d938e172f23b8f9266	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090101010-00cce9f1d03944bfc839	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090000000-f372e3204e88dfa0fac6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0089-2970000000-19bb9d5854402bda7386	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0190200000-21f48ac2697d0d52ecd2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udi-0090000000-65cde820e99b7330181c	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-0194400000-29efa8833365732bd0d9	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-c52f4b92c3ebc772069d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-2290000000-8c00534d044e8a4e8e17	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-1173900000-06545d43f6fa1210591a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1091000000-d49a71a5c4f62e485da7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-3390000000-2d121e77ef35344d0179	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Phenol-Explorer ID

DrugBank ID

HMDB ID

CRC / DFC (Dictionary of Food Compounds) ID

CMR01-H:HFG13-P

EAFUS ID

Not Available

Dr. Duke ID

DAIDZIN

BIGG ID

Not Available

KNApSAcK ID

C00002518

HET ID

DZN

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Daidzin

Phenol-Explorer Metabolite ID

403

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti alcoholic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti dipsomanic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
estrogenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hypotensive			DUKE
lipase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Daidzin (FDB012225)

Structure for FDB012225 (Daidzin)