Showing Compound Daphnetin (FDB002652)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:28 UTC

Update date

2025-11-18 22:39:06 UTC

Primary ID

FDB002652

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Daphnetin

Description

7,8-dihydroxy-2h-chromen-2-one, also known as daphnetin or 7,8-dihydroxycoumarin, is a member of the class of compounds known as 7,8-dihydroxycoumarins. 7,8-dihydroxycoumarins are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively. 7,8-dihydroxy-2h-chromen-2-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 7,8-dihydroxy-2h-chromen-2-one can be found in chickpea and watermelon, which makes 7,8-dihydroxy-2h-chromen-2-one a potential biomarker for the consumption of these food products.

CAS Number

486-35-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
7,8-Dihydroxy-2H-1-benzopyran-2-one	ChEBI
Daphnetin	ChEBI
Daphnetol	ChEBI
7,8-Dihydroxycoumarin, 8CI	db_source

Predicted Properties

Property	Value	Source
Water Solubility	4.1 g/L	ALOGPS
logP	1.49	ALOGPS
logP	1.83	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8.05	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.51 m³·mol⁻¹	ChemAxon
Polarizability	16.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H6O4

IUPAC name

7,8-dihydroxy-2H-chromen-2-one

InChI Identifier

InChI=1S/C9H6O4/c10-6-3-1-5-2-4-7(11)13-9(5)8(6)12/h1-4,10,12H

InChI Key

ATEFPOUAMCWAQS-UHFFFAOYSA-N

Isomeric SMILES

OC1=C(O)C2=C(C=CC(=O)O2)C=C1

Average Molecular Weight

178.1415

Monoisotopic Molecular Weight

178.02660868

Classification

Description

Belongs to the class of organic compounds known as 7,8-dihydroxycoumarins. These are coumarins bearing two hydroxyl groups at the C7- and C8-positions of the coumarin skeleton, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7,8-dihydroxycoumarins

Alternative Parents

Substituents

7,8-dihydroxycoumarin
7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:17313 )
coumarins (C03093 )
a small molecule (78-DIHYDROXYCOUMARIN )

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 60.68%; H 3.39%; O 35.92%	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	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Daphnetin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-4092000000-9e5038db7ca8b2f48a66	Spectrum
Predicted GC-MS	Daphnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002b-0900000000-b6fd4c52b23487904db8	Spectrum
Predicted GC-MS	Daphnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Daphnetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-0700d03e5ae6c4b59442	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-19dea9f6a73a24977e99	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-005i-8900000000-4e3f713c5e0fbdf7f377	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-a92e6e66acbf10b778db	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-8d9b4d2aefac4154e7c6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-3900000000-4e4784e5add130cd54cf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-0c76ac6afb0914fb6c47	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-2ba47ad7a3615851411d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-8900000000-0ad4d4b325ad3947d979	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-268d2373aed653cef90c	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-2fbadbe863832e01955d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-057i-7900000000-9aad201dec97e4bbdf98	2021-09-25	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

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CMX24-U:CMX24-U

EAFUS ID

Not Available

Dr. Duke ID

DAPHNETIN

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

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
Analgesic	35480	An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Cholagogue		An agent that stimulates the release of bile from the gallbladder, promoting digestion and relieving bile duct issues. Therapeutically, it aids in treating gallstones, jaundice, and liver disorders, while also supporting digestive health.	DUKE
Immunostimulant	50847	An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE