Structure Database (LMSD)

Common Name
Pinocembrin
Systematic Name
(S)-2,3-Dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one
Synonyms
LM ID
LMPK12140214
Formula
Exact Mass
Calculate m/z
256.07356
Status
Curated

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

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/
Pinus (#3337)
Pinopsida (#58019)
Constituents of Pine Heartwood. XXVI. A General Discussion.,
Acta Chem Scand, 1951

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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Created at
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Updated at
3rd Jul 2025