Structure

InChI Key DKYWVDODHFEZIM-NSHDSACASA-N
Smiles C[C@H](C(=O)O)c1cccc(C(=O)c2ccccc2)c1
InChI
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)/t11-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H14O3
Molecular Weight 254.29
AlogP 3.11
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 54.37
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
Cyclooxygenase inhibitor INHIBITOR PubMed PubMed PubMed PubMed PubMed PubMed PubMed PubMed
Protein: Cyclooxygenase

Description: Prostaglandin G/H synthase 1

Organism : Homo sapiens

P23219 ENSG00000095303
Protein: Cyclooxygenase

Description: Prostaglandin G/H synthase 2

Organism : Homo sapiens

P35354 ENSG00000073756
Assay Description Organism Bioactivity Reference
Concentration required for 50% inhibition against Prostaglandin G/H synthase 2 from human None 27.0 nM
Concentration required for 50% inhibition against Prostaglandin G/H synthase 1 from human None 1.9 nM
Inhibition of CXCL8-induced chemotaxis in human polymorphonuclear cells Homo sapiens 50.0 nM
Inhibition of lipopolysaccharide-induced PGE-2 production at 10e-5 M Mus musculus 99.0 %
Inhibition of CXCL8-induced chemotaxis of human polymorphonuclear cells at 10e-8 M Homo sapiens 52.0 %
DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) Homo sapiens 4.483 nM
DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) None 230.0 nM
Anti-inflammatory activity in Rattus norvegicus Fischer-344 (rat) assessed as inhibition of carrageenan-induced paw oedema at 0.30 mmol/kg, ip administered 5 min before FCA challenge measured after 3 hr relative to control Rattus norvegicus 42.0 %

Related Entries

Cross References

Resources Reference
ChEBI 76128
ChEMBL CHEMBL75435
DrugBank DB09214
DrugCentral 833
FDA SRS 6KD9E78X68
Human Metabolome Database HMDB0041873
PDB 9KL
PharmGKB PA166049175
PubChem 667550
SureChEMBL SCHEMBL66987
ZINC ZINC000000005560