DAPHNETIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H6O4
Molecular Weight	178.1415
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C2C=CC(=O)OC2=C1O

InChI

InChIKey=ATEFPOUAMCWAQS-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C9H6O4
Molecular Weight	178.1415
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28119924 | https://www.ncbi.nlm.nih.gov/pubmed/27297262 | https://www.ncbi.nlm.nih.gov/pubmed/17094616

Daphnetin (DAP), a natural coumarin derivative isolated from Chinese medicinal herbs, possesses abundant biological activities, such as anti-inflammatory, antioxidant, antimalarial and anti-arthritic. Experiments on mice have shown, that DAP exerts neuroprotective and anti-inflammatory effects, and the potential mechanism is involved the inhibition of TLR4/NF-κB mediated inflammatory signaling pathway. Besides, DAP, a multi-targeted medication, can have the application for the anti-angiogenesis and cancer therapy, through the inhibition of the IKKs/IκBα/NF-κB, Src/FAK/ERK1/2 and Akt signaling pathways. It is known, that protein kinases play key roles in the control of cell proliferation, differentiation, and metabolism. Daphnetin inhibits tyrosine-specific protein kinase, EGF receptor, serine/threonine-specific protein kinases, including cAMP-dependent protein kinase (PKA) and protein kinase C (PKC).

Approval Year

Targets

Primary Target	Pharmacology	Potency
Epidermal growth factor receptor 46 Target ID: P00533\|\|\|Q9GZX1 Gene ID: 1956.0 Gene Symbol: EGFR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10403826	Inhibitor 8297	7.67 µM [IC50]
cAMP-dependent protein kinase (PKA) 18 Target ID: CHEMBL2094138 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10403826	Inhibitor 8297	9.33 µM [IC50]
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10403826	Inhibitor 8297	25.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
[Effect of daphnetin on the exo-erythrocytic stage of rodent malaria].	2001	12572020
[Sensitization and crossreaction of simple coumarins].	2001 Jan	11201168
Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L.	2001 Jul	11515721
In vitro inhibitory effects of Daphne oleoides ssp. oleoides on inflammatory cytokines and activity-guided isolation of active constituents.	2001 Mar 21	11292319
In vitro antimalarial effect of daphnetin relating to its iron-chelating activity.	2002	12567565
In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines.	2002 Sep 8	12049815
[Effect of daphnetin on SOD activity and DNA synthesis of Plasmodium falciparum in vitro].	2003	14628347
Daphnetin methylation by a novel O-methyltransferase is associated with cold acclimation and photosystem II excitation pressure in rye.	2003 Feb 28	12480941
Identification and characterisation of the chinese herb Langdu by LC-MS/MS analysis.	2003 Jan-Feb	12597254
Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities.	2004	15579073
Comparative study on schizontocidal activity of recrystallized or crude daphnetin against malaria parasites.	2004 Dec	15745243
[Additive therapeutic effect of a combination of artemether and daphnetin against Plasmodium berghei in mice].	2004 Jun	15597713
Daphnetin induced differentiation of human renal carcinoma cells and its mediation by p38 mitogen-activated protein kinase.	2004 May 1	15081877
Binding of the bioactive component daphnetin to human serum albumin demonstrated using tryptophan fluorescence quenching.	2004 May 17	15468244
Spectrofluorimetric study of the binding of daphnetin to bovine serum albumin.	2004 May 28	15137995
Iron chelator daphnetin against Pneumocystis carinii in vitro.	2004 Nov	15569490
[Studies on the chemical constituents in roots of Daphne odora var. atrocaulis].	2005 Apr	16011095
Solid-phase extraction of esculetin from the ash bark of Chinese traditional medicine by using molecularly imprinted polymers.	2005 Jan 7	15679140
[In vitro effect of daphnetin on cytochrome C oxidase and ribonucleotide reductase of plasmodium falciparum].	2006 Jun	17094616
Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida).	2006 May 17	19127719
In vitro potentiation of antimalarial activities by daphnetin derivatives against Plasmodium falciparum.	2006 Oct	17190189
Determination of kava lactones and flavonoid glycoside in Scorzonera austriaca by capillary zone electrophoresis.	2007 Feb 19	17034980
Multi-substrate flavonol O-glucosyltransferases from strawberry (Fragaria x ananassa) achene and receptacle.	2008	18487633
Recent advances in the compound-oriented and pattern-oriented approaches to the quality control of herbal medicines.	2008 Aug 4	18680568
Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells.	2008 Mar 1	18060791
Therapeutic effects of daphnetin on adjuvant-induced arthritic rats.	2008 Nov 20	18835428
[Intestinal absorption of daphnetin by rats single pass perfusion in situ].	2009 Aug	20055163
Effect of chemical enhancers on percutaneous absorption of daphnetin in isopropyl myristate vehicle across rat skin in vitro.	2009 May	19280376
Potential utility of daphnetin as a novel treatment for pemphigus vulgaris.	2010 Aug	20823801
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.	2010 Dec 13	21144003
Antioxidant activities of coumarins from Korean medicinal plants and their structure-activity relationships.	2010 Jan	19468986
Identification and characterization of human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of daphnetin.	2010 Jun	20176691
Novel insights into the mechanism of decreased expression of type X collagen in human mesenchymal stem cells from patients with osteoarthritis cultured on nitrogen-rich plasma polymers: implication of cyclooxygenase-1.	2010 Sep 1	20225218

Patents

Sample Use Guides

In Vivo Use Guide

in rats: six sprague-dawley rats received intragastric administration of D. giraldii extract (daphnetin, daphnoretin and daphneticin were 88.40, 3.24 and 4.28 mg•kg⁻¹, respectively).

Route of Administration: Intragastric

In Vitro Use Guide

To test the in vitro effect of daphnetin on cytochrome C oxidase (COX) and ribonucleotide reductase (RNR) activity of Plasmodium falciparum. The parasites synchronized with sorbitol in vitro was treated by daphnetin and daphnetin-Fe complex. The inhibition level of the COX activity by daphnetin after being treated for 2, 4, 8 and 12 h were 0.6%, 73% and 80% respectively and the inhibition level by daphnetin at different concentrations (0.1, 1, 100 and 1 mmol/L) for 6h was 3%, 31%, 53% and 84%, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:50:33 GMT 2023` Edited by `admin` on `Fri Dec 15 18:50:33 GMT 2023`
Record UNII	XC84571RD2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DAPHNETIN

Official Name

English

DAPHNETIN [INCI]

Common Name

English

NSC-633563

Code

English

7,8-DIHYDROXYCOUMARIN

Systematic Name

English

7,8-DIHYDROXY-2H-1-BENZOPYRAN-2-ONE

Systematic Name

English

2H-1-BENZOPYRAN-2-ONE, 7,8-DIHYDROXY-

Systematic Name

English

DAPHNETIN [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

5280569