Structure Database (LMSD)
Common Name
Pinocembrin
Systematic Name
Synonyms
3D model of Pinocembrin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Pinocembrin is a flavonoid that has been found in Eucalyptus, and has diverse biological activities.1,2,3,4,5 It induces apoptosis in, and inhibits the migration of, SKOV3 ovarian cancer cells when used at a concentration of 200 µM.2 Pinocembrin (5 mg/kg) reduces lesion volume, as well as brain microglial activation and production of IL-1β, IL-6, and TNF-α in a mouse model of collagenase-induced intracerebral hemorrhage (ICH).3 It prevents increases in plasma and kidney malondialdehyde (MDA) levels, glomeruli lobulation, mesangial expansion, and tubule vacuolization and occlusion, and it decreases hepatic cholesterol, triglyceride, and LDL levels in a rat model of diabetic nephropathy.4 Pinocembrin (20 and 50 mg/kg) reduces pulmonary edema, as well as neutrophil, lymphocyte, and macrophage infiltration in a mouse model of LPS-induced lung injury.5
This information has been provided by Cayman Chemical
References
1. Soromou, L.-W., Chu, X., Jiang, L., et al. In vitro and in vivo protection provided by pinocembrin against lipopolysaccharide-induced inflammatory responses. Int. Immunol. 14(1), 66-74 (2012).
2. Granados-Pineda, J., Uribe-Uribe, N., Garía-López, P., et al. Effect of pinocembrin isolated from Mexican brown propolis on diabetic nephropathy. Molecules 23(4), 1-19 (2018).
3. Lan, X., Han, X., Li, Q., et al. Pinocembrin protects hemorrhagic brain primarily by inhibiting toll-like receptor 4 and reducing M1 phenotype microglia. Brain Behav. Immun. 61, 326-339 (2017).
4. Gao, J., Lin, S., Gao, Y., et al. Pinocembrin inhibits the proliferation and migration and promotes the apoptosis of ovarian cancer cells through down-regulating the mRNA levels of N-cadherin and GABAB receptor. Biomed. Pharmacother. 120, 109505 (2019).
5. Rasul, A., Millimouno, F.M., Eltayb, W.A., et al. Pinocembrin: A novel natural compound with versatile pharmacological and biological activities. Biomed. Res. Int. 379850 (2013).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
URFCJEUYXNAHFI-ZDUSSCGKSA-N
InChi (Click to copy)
InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2/t13-/m0/s1
SMILES (Click to copy)
C1(O)C=C2O[C@]([H])(C3C=CC=CC=3)CC(=O)C2=C(O)C=1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
PDB ID
Calculated Physicochemical Properties
Heavy Atoms
19
Rings
3
Aromatic Rings
2
Rotatable Bonds
1
Van der Waals Molecular Volume
225.86
Topological Polar Surface Area
68.83
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
2.80
Molar Refractivity
68.53
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Updated at
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