Showing Compound 5,7-Dihydroxyisoflavone (FDB002620)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:27 UTC

Update date

2020-02-24 19:10:34 UTC

Primary ID

FDB002620

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5,7-Dihydroxyisoflavone

Description

5,7-Dihydroxyisoflavone 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. Thus, 5,7-dihydroxyisoflavone is considered to be a flavonoid. 5,7-Dihydroxyisoflavone is a bitter tasting compound. 5,7-Dihydroxyisoflavone has been detected, but not quantified in, nuts and peanuts (Arachis hypogaea). This could make 5,7-dihydroxyisoflavone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,7-Dihydroxyisoflavone.

CAS Number

4044-00-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2',3'-Dimethyl-2-diphenylaminecarboxylic acid	HMDB
2-((2,3-Dimethylphenyl)amino)-benzoic acid	HMDB
2-((2,3-Dimethylphenyl)amino)benzoic acid	HMDB
2-(2,3-dimethylanilino)Benzoic acid	HMDB
2-(2,3-Dimethylphenyl)amino-benzoic acid	HMDB
2-[(2,3-Dimethylphenyl)amino]-benzoic acid	HMDB
2-[(2,3-Dimethylphenyl)amino]benzoic acid	HMDB
5,7-Dihydroxy-3-phenyl-4H-1-benzopyran-4-one, 9ci	HMDB
Ac. mefenamico	HMDB
Acid, mefenamic	HMDB, MeSH
Acid, mefenaminic	HMDB
acido Mefenamico	HMDB
Acidum mefenamicum	HMDB
Antigen brand OF mefenamic acid	HMDB
apo Mefenamic	HMDB, MeSH
apo-Mefenamic	HMDB, MeSH
Apomefenamic	HMDB
Apotex brand OF mefenamic acid	HMDB
Aps brand OF mefenamic acid	HMDB
Ashbourne brand OF mefenamic acid	HMDB
Bafameritin-m	HMDB
Bafhameritin-m	HMDB
Bonabol	HMDB
Chemidex brand OF mefenamic acid	HMDB
Clonmel brand OF mefenamic acid	HMDB
Contraflam	HMDB, MeSH
Coslan	HMDB, MeSH
Dysman	HMDB, MeSH
Elan brand OF mefenamic acid	HMDB
Farmasierra brand OF mefenamic acid	HMDB
Fenamin	HMDB
First horizon brand OF mefenamic acid	HMDB
Forte, ponstan	HMDB
Lysalgo	HMDB
Mefac	HMDB, MeSH
Mefacit	HMDB, MeSH
Mefedolo	HMDB
Mefenamate	HMDB
Mefenamic acid	HMDB, MeSH
Mefenamic acid (JP15/usp/inn)	HMDB
Mefenaminic acid	HMDB, MeSH
Mefic	HMDB, MeSH
Mephenamic acid	HMDB
Mephenaminic acid	HMDB
Methenamic acid	HMDB
Mycasaal	HMDB
N-(2, 3-Dimethylphenyl)anthranilic acid	HMDB
N-(2,3-Dimethylphenyl)anthranilic acid	HMDB
N-(2,3-Xylyl)-2-aminobenzoic acid	HMDB
N-(2,3-Xylyl)-anthranilic acid	HMDB
N-(2,3-Xylyl)anthranilic acid	HMDB
N-2,3-Xylyl-anthranilic acid	HMDB
N-2,3-Xylylanthranilic acid	HMDB
Namphen	HMDB
Nu mefenamic	HMDB, MeSH
Nu pharm brand OF mefenamic acid	HMDB
Nu-mefenamic	HMDB, MeSH
Nu-pharm brand OF mefenamic acid	HMDB
Numefenamic	HMDB
Parke davis brand OF mefenamic acid	HMDB
Parkemed	HMDB, MeSH
Pfizer brand OF mefenamic acid	HMDB
Pharmascience brand OF mefenamic acid	HMDB
Pinalgesic	HMDB, MeSH
Pinewood brand OF mefenamic acid	HMDB
PMS Mefenamic acid	HMDB, MeSH
PMS-Mefenamic acid	HMDB, MeSH
Ponalar	HMDB, MeSH
Ponalgic	HMDB, MeSH
Ponmel	HMDB, MeSH
Ponstan	HMDB, MeSH
Ponstan forte	HMDB, MeSH
Ponstel	HMDB, MeSH
Ponstil	HMDB
Ponstyl	HMDB
Ponsyl	HMDB, MeSH
Pontal	HMDB, MeSH
Rolan	HMDB
Rowa brand OF mefenamic acid	HMDB
Tamany bonsan	HMDB
Tanston	HMDB
Vialidon	HMDB
Warner lambert brand OF mefenamic acid	HMDB
Warner-lambert brand OF mefenamic acid	HMDB
2-(2,3-Dimethylanilino)benzoic acid	HMDB
5,7-Dihydroxy-3-phenyl-4H-1-benzopyran-4-one, 9CI	db_source
Acido mefenamico	HMDB
Apo mefenamic	HMDB
Apo-mefenamic	HMDB
Mefenamic acid (jp15/usp/inn)	HMDB
PMS mefenamic acid	HMDB
PMS-mefenamic acid	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.43	ALOGPS
logP	3.38	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.7 m³·mol⁻¹	ChemAxon
Polarizability	25.54 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

C15H10O4

IUPAC name

5,7-dihydroxy-3-phenyl-4H-chromen-4-one

InChI Identifier

InChI=1S/C15H10O4/c16-10-6-12(17)14-13(7-10)19-8-11(15(14)18)9-4-2-1-3-5-9/h1-8,16-17H

InChI Key

PJJGZPJJTHBVMX-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(O)=C2C(OC=C(C2=O)C2=CC=CC=C2)=C1

Average Molecular Weight

254.2375

Monoisotopic Molecular Weight

254.057908808

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-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050160 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 70.86%; H 3.96%; O 25.17%	DFC
Melting Point	Mp 205° (195-196°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	4.2
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
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	5,7-Dihydroxyisoflavone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fb9-0590000000-e2ff2001e153e6cf7449	Spectrum
Predicted GC-MS	5,7-Dihydroxyisoflavone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-3429000000-b6b1b42102055591ce3c	Spectrum
Predicted GC-MS	5,7-Dihydroxyisoflavone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5,7-Dihydroxyisoflavone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0aor-0890000000-cd3ff09fc3580b809662	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0940000000-95fc529c3e873aac5713	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-29e06e81d4c558ee48ef	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-59c5e3ac44232fff89f8	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-5980000000-90b06001f89cd194ecc5	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-9bc12677fe73322192b4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-e3bcd05c9ccad6986565	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2950000000-5486ae9d8cb7e66c3a34	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-ff2e7266db5d933feb85	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-19b080c226d8f95441d3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02t9-4970000000-a9fd6abf301dcf31ceb7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-88382720cb3b98a4d462	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-88382720cb3b98a4d462	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-102i-2950000000-6047a831f7ef49c45bbf	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB00784

HMDB ID

HMDB30699

CRC / DFC (Dictionary of Food Compounds) ID

CMS43-A:CMS43-A

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00009814

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

Not Available

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

Not Available

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

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.