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
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
| 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 |
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 | Condition | Potency |
|---|---|---|---|
Target ID: P00533|||Q9GZX1 Gene ID: 1956.0 Gene Symbol: EGFR Target Organism: Homo sapiens (Human) |
7.67 µM [IC50] | ||
Target ID: CHEMBL2094138 |
9.33 µM [IC50] | ||
Target ID: CHEMBL2093867 |
25.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Traditional herbal medicine in far-west Nepal: a pharmacological appraisal. | 2010-12-13 |
|
| 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. | 2010-09-01 |
|
| Potential utility of daphnetin as a novel treatment for pemphigus vulgaris. | 2010-08 |
|
| Identification and characterization of human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of daphnetin. | 2010-06 |
|
| Antioxidant activities of coumarins from Korean medicinal plants and their structure-activity relationships. | 2010-01 |
|
| [Intestinal absorption of daphnetin by rats single pass perfusion in situ]. | 2009-08 |
|
| Effect of chemical enhancers on percutaneous absorption of daphnetin in isopropyl myristate vehicle across rat skin in vitro. | 2009-05 |
|
| Therapeutic effects of daphnetin on adjuvant-induced arthritic rats. | 2008-11-20 |
|
| Recent advances in the compound-oriented and pattern-oriented approaches to the quality control of herbal medicines. | 2008-08-04 |
|
| Structural insights into hydroxycoumarin-induced apoptosis in U-937 cells. | 2008-03-01 |
|
| Multi-substrate flavonol O-glucosyltransferases from strawberry (Fragaria x ananassa) achene and receptacle. | 2008 |
|
| Determination of kava lactones and flavonoid glycoside in Scorzonera austriaca by capillary zone electrophoresis. | 2007-02-19 |
|
| In vitro potentiation of antimalarial activities by daphnetin derivatives against Plasmodium falciparum. | 2006-10 |
|
| [In vitro effect of daphnetin on cytochrome C oxidase and ribonucleotide reductase of plasmodium falciparum]. | 2006-06 |
|
| Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida). | 2006-05-17 |
|
| [Studies on the chemical constituents in roots of Daphne odora var. atrocaulis]. | 2005-04 |
|
| Solid-phase extraction of esculetin from the ash bark of Chinese traditional medicine by using molecularly imprinted polymers. | 2005-01-07 |
|
| Comparative study on schizontocidal activity of recrystallized or crude daphnetin against malaria parasites. | 2004-12 |
|
| Iron chelator daphnetin against Pneumocystis carinii in vitro. | 2004-11 |
|
| [Additive therapeutic effect of a combination of artemether and daphnetin against Plasmodium berghei in mice]. | 2004-06 |
|
| Spectrofluorimetric study of the binding of daphnetin to bovine serum albumin. | 2004-05-28 |
|
| Binding of the bioactive component daphnetin to human serum albumin demonstrated using tryptophan fluorescence quenching. | 2004-05-17 |
|
| Daphnetin induced differentiation of human renal carcinoma cells and its mediation by p38 mitogen-activated protein kinase. | 2004-05-01 |
|
| Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. | 2004 |
|
| Daphnetin methylation by a novel O-methyltransferase is associated with cold acclimation and photosystem II excitation pressure in rye. | 2003-02-28 |
|
| Identification and characterisation of the chinese herb Langdu by LC-MS/MS analysis. | 2003-02-25 |
|
| [Effect of daphnetin on SOD activity and DNA synthesis of Plasmodium falciparum in vitro]. | 2003 |
|
| In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines. | 2002-09-08 |
|
| In vitro antimalarial effect of daphnetin relating to its iron-chelating activity. | 2002 |
|
| Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L. | 2001-07 |
|
| In vitro inhibitory effects of Daphne oleoides ssp. oleoides on inflammatory cytokines and activity-guided isolation of active constituents. | 2001-03-21 |
|
| [Sensitization and crossreaction of simple coumarins]. | 2001-01 |
|
| [Effect of daphnetin on the exo-erythrocytic stage of rodent malaria]. | 2001 |
Sample Use Guides
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
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
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admin
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Edited
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| Record UNII |
XC84571RD2
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| Record Status |
Validated (UNII)
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| Record Version |
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