Structure Database (LMSD)

Common Name
Orsellinic acid
Systematic Name
Synonyms
LM ID
LMPK13010001
Formula
C8H8O4
Exact Mass
Calculate m/z
168.04226
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Aromatic polyketides [PK13]
Monocyclic aromatic polyketides [PK1301]

Biological Context

Orsellinic acid is a fungal metabolite and benzoic acid derivative with antioxidant and neuroprotective activities.1,2 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals with an IC50 value of 5 mM.1 Orsellinic acid (1 μg/ml) prevents PARP cleavage induced by platelet-activating factor (PAF) in PC12-AC cells and PAF-induced cytotoxicity in PAF receptor null (Pafr-/-) mouse cerebellar granule cells.2

This information has been provided by Cayman Chemical

References

1. Ryan, S.D., Harris, C.S., Mo, F., et al. Platelet activating factor-induced neuronal apoptosis is initiated independently of its G-protein coupled PAF receptor and is inhibited by the benzoate orsellinic acid. J. Neurochem. 103(1), 88-97 (2007).
2. Lopes, T.I.B., Coelho, R.H., Toshida, N.C., et al. Radical-scavenging activity of orsellinates. Chem. Pharm. Bull. (Tokyo) 56(11), 1551-1554 (2008).

String Representations

InChiKey (Click to copy)
AMKYESDOVDKZKV-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)
SMILES (Click to copy)
C1(C(=O)O)C(O)=CC(O)=CC=1C

Other Databases

Wikipedia
Orsellinic_acid
KEGG ID
C01839
CHEBI ID
32807
PubChem CID
68072
Cayman ID
22708
PDB ID
6X7

Calculated Physicochemical Properties

Heavy Atoms 12
Rings 1
Aromatic Rings 1
Rotatable Bonds 1
Van der Waals Molecular Volume 148.30
Topological Polar Surface Area 77.76
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 1.10
Molar Refractivity 41.47

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Updated at
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