Showing Compound Prunetin (FDB012400)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:09 UTC

Update date

2019-11-26 03:06:42 UTC

Primary ID

FDB012400

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Prunetin

Description

Prunetin, also known as padmakastein, belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, prunetin is considered to be a flavonoid lipid molecule. Prunetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Prunetin is a bitter tasting compound. Prunetin has been detected, but not quantified in, several different foods, such as herbs and spices, prunus (cherry, plum), sour cherries, and tea. This could make prunetin a potential biomarker for the consumption of these foods.

CAS Number

552-59-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4',5-Dihydroxy-7-methoxygenistein	ChEBI
4',5-Dihydroxy-7-methoxyisoflavone	ChEBI
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone	ChEBI
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one	ChEBI
7-O-Methyl-genistein	ChEBI
Padmakastein	ChEBI
Prunusetin	ChEBI
5,4'-Dihydroxy-7-methoxyisoflavone	HMDB
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 9ci	HMDB
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one	HMDB
Isoflavone, 4',5-dihydroxy-7-methoxy- (7ci,8ci)	HMDB
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 9CI	db_source
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one	biospider
5,4'-dihydroxy-7-methoxyisoflavone	biospider
Isoflavone, 4',5-dihydroxy-7-methoxy- (7CI,8CI)	biospider
Prunetin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.059 g/L	ALOGPS
logP	3.36	ALOGPS
logP	3.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.71 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

C16H12O5

IUPAC name

5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

InChI Identifier

InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

InChI Key

KQMVAGISDHMXJJ-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1

Average Molecular Weight

284.267

Monoisotopic Molecular Weight

284.068473486

Classification

Description

Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylisoflavones

Alternative Parents

Substituents

7-o-methylisoflavone
Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:8600 )
methoxyisoflavone (CHEBI:8600 )
isoflavones (C10521 )
Isoflavonoids (C10521 )
Isoflavonoids (LMPK12050353 )
a small molecule (CPD-3521 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Biofluid and excreta:

Urine

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 67.60%; H 4.25%; O 28.14%	DFC
Melting Point	Mp 246-248°	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	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Prunetin, non-derivatized, GC-MS Spectrum	splash10-03di-1932800000-7ba8925a2b1306b10b50	Spectrum
GC-MS	Prunetin, non-derivatized, GC-MS Spectrum	splash10-03di-1932800000-7ba8925a2b1306b10b50	Spectrum
Predicted GC-MS	Prunetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-0490000000-568458ba8831c097f5c5	Spectrum
Predicted GC-MS	Prunetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-08ml-3439700000-90e7b4e47d986f3bfb5f	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0190000000-b6ecb3ccb54bdeacbe00	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0190000000-b6ecb3ccb54bdeacbe00	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-11b97ad586d2e24e7115	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014r-0090000000-fb797f4684174e26b1d0	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-6db4d2441911d696b121	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0090000000-306c2baf58cc6c40c407	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0159-0090000000-a85c6c3392aa2541b48c	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-11b97ad586d2e24e7115	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014r-0090000000-fb797f4684174e26b1d0	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-6db4d2441911d696b121	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-306c2baf58cc6c40c407	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0159-0090000000-a85c6c3392aa2541b48c	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014r-0090000000-fb797f4684174e26b1d0	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0090000000-6db4d2441911d696b121	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 19V, positive	splash10-002r-0290000000-e0d4e56550195007ab89	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 19V, positive	splash10-0690-0690000000-292dcb6a0c7801e87353	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-280a25523108ad3de6f1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-8512eb234e9b55c8fabc	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbi-2790000000-911d7dc4d9e528af001b	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-3539a40fa0eaf6326969	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-bb3562f94d2cef4ead46	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gb9-3980000000-4d720fa6bb02944fb579	Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

8600

Phenol-Explorer ID

881

DrugBank ID

Not Available

HMDB ID

HMDB34127

CRC / DFC (Dictionary of Food Compounds) ID

HGS77-A:HGS77-A

EAFUS ID

Not Available

Dr. Duke ID

PRUNETIN

BIGG ID

Not Available

KNApSAcK ID

C00002564

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

Prunetin

Phenol-Explorer Metabolite ID

881

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
fungicide	24127	A substance used to destroy fungal pests.	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

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).