Showing Compound 8-Hydroxygenistein (FDB012252)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:04 UTC

Update date

2019-11-26 03:06:29 UTC

Primary ID

FDB012252

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

8-Hydroxygenistein

Description

8-hydroxygenistein is a member of the class of compounds known as isoflavones. Isoflavones are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. 8-hydroxygenistein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 8-hydroxygenistein can be found in a number of food items such as scarlet bean, mung bean, lima bean, and adzuki bean, which makes 8-hydroxygenistein a potential biomarker for the consumption of these food products.

CAS Number

13539-27-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4',5,7,8-Tetrahydroxyisoflavone	db_source
5,7,8-Trihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CI	db_source
5,7,8,4'-Tetrahydroxyisoflavone	manual
8-Hydroxygenistein	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.68	ALOGPS
logP	2.77	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.79	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.66 m³·mol⁻¹	ChemAxon
Polarizability	27.51 Å³	ChemAxon
Number of Rings	3	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

C15H10O6

IUPAC name

5,7,8-trihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

InChI Identifier

InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)9-6-21-15-12(13(9)19)10(17)5-11(18)14(15)20/h1-6,16-18,20H

InChI Key

ZKZCRGBCWBCSNJ-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(C=C1)C1=COC2=C(O)C(O)=CC(O)=C2C1=O

Average Molecular Weight

286.2363

Monoisotopic Molecular Weight

286.047738052

Classification

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 62.94%; H 3.52%; O 33.54%	DFC
Melting Point	Not Available
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	Not Available
Spectroscopic UV Data	310 () (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-adc189b8bf74cddc783b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1090000000-2322b06886c69afdea71	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014j-9860000000-4fc8d65cf8c987a3efba	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-8a897aee55c787a49452	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0190000000-fa75e4d164bef7f32738	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-5930000000-9444e825b1398336ea1c	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-ad6070afb384abda8f3b	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-729519815713f93408c4	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-067l-0590000000-a3d07c68527d75215203	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-3713e1ac18e8a67ad454	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0190000000-16a410866b128e56bea6	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1920000000-e3c669b4718b7f829787	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HFL43-X:HFL43-X

EAFUS ID

Not Available

Dr. Duke ID

8-HYDROXYGENISTEIN|HYDROXYGENISTEIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

842

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
catechol O-methyltransferase inhibitor	48406	An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6).	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
phytoalexin	26115	A toxin made by a plant that acts against an organism attacking it.	DUKE