Structure Database (LMSD)
Common Name
Hispidulin
Systematic Name
Synonyms
3D model of Hispidulin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Hispidulin is a flavonoid originally isolated from A. montana with diverse biological activities.1,2,3,4,5 It inhibits platelet aggregation induced by platelet-activating factor (PAF), arachidonic acid , and ADP (IC50s = 20, 4, and 13 μM, respectively).1 Hispidulin inhibits RANKL-induced osteoclastic differentiation of RAW 264.7 cells and bone marrow-derived macrophages (BMMs).2 In vivo, hispidulin (25 μg/kg) inhibits LPS-induced bone resorption in mice. It inhibits sphingosine kinase 1 (SPHK1) and induces ceramide accumulation and apoptosis in Caki-2 renal carcinoma cells in vitro and inhibits tumor growth in a Caki-2 mouse xenograft model.3 Pretreatment with hispidulin (40 mg/kg) reduces cognitive deficits in the Morris water maze induced by sevoflurane in aged rats.4 It also decreases infarct size and brain edema in a rat model of focal cerebral ischemia and reperfusion injury.5
This information has been provided by Cayman Chemical
References
3. Gao, H., Gao, M.-Q., Peng, J.-J., et al. Hispidulin mediates apoptosis in human renal cell carcinoma by inducing ceramide accumulation. Acta Pharmacol. Sin. 38(12), 1618-1631 (2017).
4. Huang, L., Huang, K., and Ning, H. Autophagy induction by hispidulin provides protection against sevoflurane-induced neuronal apoptosis in aged rats. Biomed. Pharmacother. 98, 460-468 (2018).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
IHFBPDAQLQOCBX-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H12O6/c1-21-16-11(19)7-13-14(15(16)20)10(18)6-12(22-13)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3
SMILES (Click to copy)
C1(O)=CC2OC(C3C=CC(O)=CC=3)=CC(=O)C=2C(O)=C1OC
Other Databases
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
22
Rings
3
Aromatic Rings
3
Rotatable Bonds
2
Van der Waals Molecular Volume
247.20
Topological Polar Surface Area
100.13
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
6
logP
3.49
Molar Refractivity
79.57
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Updated at
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