AFCDB: Chrysin (FDB015535)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:54 UTC

Update date

2019-11-26 03:11:47 UTC

Primary ID

FDB015535

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Chrysin

Description

5,7-Dihydroxyflavone belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, 5,7-dihydroxyflavone is considered to be a flavonoid. 5,7-Dihydroxyflavone is a bitter tasting compound. 5,7-Dihydroxyflavone has been detected, but not quantified in, several different foods, such as carrots (Daucus carota ssp. sativus), sour cherries (Prunus cerasus), sweet oranges (Citrus sinensis), and wild carrots (Daucus carota). This could make 5,7-dihydroxyflavone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 5,7-Dihydroxyflavone.

CAS Number

480-40-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.01	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.64	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	70.93 m³·mol⁻¹	ChemAxon
Polarizability	25.73 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-2-phenyl-4H-chromen-4-one

InChI Identifier

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

InChI Key

RTIXKCRFFJGDFG-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=CC=C1

Average Molecular Weight

254.2375

Monoisotopic Molecular Weight

254.057908808

Classification

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:75095 )
7-hydroxyflavonol (CHEBI:75095 )
flavones (C10028 )
Flavones and Flavonols (C10028 )
Flavones and Flavonols (LMPK12110189 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties

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	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	318 () (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Chrysin, 2 TMS, GC-MS Spectrum	splash10-001i-2839000000-d0964f24f611d1c14e95	Spectrum
GC-MS	Chrysin, non-derivatized, GC-MS Spectrum	splash10-001i-2839000000-d0964f24f611d1c14e95	Spectrum
GC-MS	Chrysin, non-derivatized, GC-MS Spectrum	splash10-001i-0619000000-53f48b2cf9bad74e8f65	Spectrum
Predicted GC-MS	Chrysin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-0690000000-b07283fbd904f2901dd6	Spectrum
Predicted GC-MS	Chrysin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00gi-4439000000-26a54787c8758b70201f	Spectrum
Predicted GC-MS	Chrysin, 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 , Negative	splash10-0002-0020900000-2dbcc5b06309066d63b5	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 26V, Negative	splash10-0udi-0290000000-bdd70471bc805c9009b2	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0fr6-0900000000-eee4ea35750adc10ef1b	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0090000000-2f6b543a5679e285552a	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 26V, Negative	splash10-0udi-0290000000-bdd70471bc805c9009b2	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0fr6-0900000000-eee4ea35750adc10ef1b	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0udi-0490000000-554518d0a352f29f8093	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0zfr-0950000000-51b2794dec3e6f6eea6a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090000000-9cc0f49937b1a8fa0b34	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090000000-66cd77f4bd910deb0103	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0290000000-10a8a1236031b97efe7a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0fr6-0920000000-19bbcaf4a2423b2cb49d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014m-0900000000-200355de722ac7f96ef7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090000000-ac2af4316665e2509d89	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0190000000-8f5ac4706417c39a2d62	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gbc-0900000000-d619653decf40895a511	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0390000000-eb3159b6ffe6b7c816b2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-006t-3930000000-3775c8b9ef4bbb0cb352	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0udi-0090000000-c8b5dd372a2667398b01	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-c8a1f1ae722a2b79308a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-191437b0a57325aec07a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-4950000000-f1f4abaafec11c500890	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-4c48fd26f99d65b20cd9	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-acfd169c302ecc539f58	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1940000000-98ef8f11854760675c83	2015-04-25	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

240

DrugBank ID

Not Available

HMDB ID

HMDB36619

CRC / DFC (Dictionary of Food Compounds) ID

KDC55-C:KDC55-C

EAFUS ID

Not Available

Dr. Duke ID

CHRYSIN

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

57D

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Chrysin

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

Descriptor	ID	Definition	Reference
anti aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti aggregant			DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti angiogenic	48422	An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.	DUKE
anti bacillary	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti estrogenic	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti gout	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti hypertensive	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti multidrug resistance			DUKE
anti mutagenic			DUKE
anti proliferant			DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti shigellic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti stress	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti thrombic	50248	Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anxiolytic	35474	Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.	DUKE
apoptotic			DUKE
aromatase inhibitor	50790	An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
caspase-3 inhibitor	37670	A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).	DUKE
caspase-9 inhibitor	37670	A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).	DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
cytochrome-CYP1A1 inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
DNA-protective			DUKE
estrogenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
hypotensive			DUKE
hypouricemic			DUKE
ICAM-1 inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
JNK 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
monoamine-oxidase 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
mutagenic			DUKE
myorelaxant			DUKE
nitric-oxide-genic			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
radioprotective	35232	Any pharmaceutical compound containing a radioisotope.	DUKE
termitifuge	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
testosterogenic			DUKE
topoisomerase-I inhibitor	50276	A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.	DUKE
vasodilator	35620	A drug used to cause dilation of the blood vessels.	DUKE
vasorelaxant			DUKE
VEGF inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
xanthine oxidase inhibitor	35634	An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).	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.	CHEBI

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).

Chrysin (FDB015535)

Structure for FDB015535 (Chrysin)