MESALAMINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
UNII 4Q81I59GXC
EPA CompTox DTXSID5024506

Structure

InChI Key KBOPZPXVLCULAV-UHFFFAOYSA-N
Smiles Nc1ccc(O)c(C(=O)O)c1
InChI
InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)

Physicochemical Descriptors

Property Name Value
Molecular Formula C7H7NO3
Molecular Weight 153.14
AlogP 0.67
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 1.0
Polar Surface Area 83.55
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 11.0

Bioactivity

Mechanism of Action Action Reference
Arachidonate 5-lipoxygenase inhibitor INHIBITOR PubMed PubMed PubMed
Protein: Arachidonate 5-lipoxygenase
Description: Polyunsaturated fatty acid 5-lipoxygenase
Organism : Homo sapiens
P09917 ENSG00000012779
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
Protein: Peroxisome proliferator-activated receptor gamma
Description: Peroxisome proliferator-activated receptor gamma
Organism : Homo sapiens
P37231 ENSG00000132170
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 7530 - - 18
Enzyme Transferase
- 280 - - -
Other cytosolic protein
- 12000 - - -
Secreted protein
- 20000 - - 52
Unclassified protein
- 490-6000 - - 49-87
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 5.0 %
Compound was tested for the inhibition of malate dehydrogenase (MDH) at 200 uM None 18.0 %
Antiarthritic activity in Freund's adjuvant-induced arthritis Wistar rat model after 13 days Rattus norvegicus 12.0 %
Antiarthritic activity in Freund's adjuvant-induced arthritis Wistar rat model after 21 days Rattus norvegicus 47.0 %
Inhibition of mouse EGFR by liquid scintillation counting Mus musculus 2.7 ug.mL-1
Antiinflammatory activity against carrageenan-induced ip dosed Wistar rat paw edema model assessed as inhibition of edema administered 30 mins prior to carrageenan challenge measured after 60 mins Rattus norvegicus 50.0 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 1 hr relative to control Rattus norvegicus 63.8 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 2 hrs relative to control Rattus norvegicus 53.2 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 3 hrs relative to control Rattus norvegicus 57.5 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 4 hrs relative to control Rattus norvegicus 52.3 %
Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 24 hrs relative to control Rattus norvegicus 38.6 %
Antiinflammatory activity in human HT-29 cells assessed as inhibition of TNF-alpha induced BCECF-AM labeled human U937 cell adhesion at 1 uM preincubated for 1 hr followed by stimulation with TNF-alpha for 3 hrs followed by further co-incubation with BCECF-AM labeled human U937 cells for 1 hr by fluorescent/light microscopic analysis Homo sapiens 3.8 %
Antiinflammatory activity in human HT-29 cells assessed as inhibition of TNF-alpha induced BCECF-AM labeled human U937 cell adhesion at 20 mM preincubated for 1 hr followed by stimulation with TNF-alpha for 3 hrs followed by further co-incubation with BCECF-AM labeled human U937 cells for 1 hr by fluorescent/light microscopic analysis Homo sapiens 52.7 %
Inhibition of TNFalpha (unknown origin)-induced adhesion of BCECF fluorescence-labeled human U937 cells to human HT-29 cells at 20 mM measured at 3 hrs post TNFalpha stimulation relative to control Homo sapiens 52.1 %
Inhibition of TNF-alpha-induced adhesion of BCECF-labeled human U937 cells to human HT-29 cells at 10 uM preincubated for 1 hr followed by TNF-alpha challenge measured after 3 hrs by fluorescence microscopic method relative to control Homo sapiens 3.7 %
Inhibition of TNF-alpha-induced adhesion of BCECF-labeled human U937 cells to human HT-29 cells at 20 mM preincubated for 1 hr followed by TNF-alpha challenge measured after 3 hrs by fluorescence microscopic method relative to control Homo sapiens 52.8 %
Inhibition of mouse recombinant glycolate oxidase expressed in Escherichia coli at 25 uM using glycolate as substrate after 1 min by sulfonated DCIP dye-based assay relative to control Mus musculus 71.9 %
Inhibition of TNFalpha-mediated adhesion of BCECF fluorescence-labeled human U937 cells to human HT-29 cells at 1 uM pretreated for 1 hr followed by BCECF fluorescence-labeled human U937 cell/TNFalpha addition and measured after 3 hrs by fluorescence assay relative to control Homo sapiens 3.5 %
Inhibition of TNFalpha-mediated adhesion of BCECF fluorescence-labeled human U937 cells to human HT-29 cells at 20 mM pretreated for 1 hr followed by BCECF fluorescence-labeled human U937 cell/TNFalpha addition and measured after 3 hrs by fluorescence assay relative to control Homo sapiens 50.5 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus -19.58 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 3.21 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae -2.18 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 3.43 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 6.42 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 1.32 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans 3.98 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -4.82 %
Inhibition of native rhodanese (unknown origin) assessed as reduction in rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis Homo sapiens 280.0 nM
Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured rhodanese refolding by measuring rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis Escherichia coli 490.0 nM
Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured soluble pig heart MDH refolding by measuring MDH enzyme activity using sodium mesoxalate as substrate after 20 to 40 mins by malachite green dye based spectrometric analysis relative to untreated control Escherichia coli 49.0 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured rhodanese refolding by measuring rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis relative to untreated control Escherichia coli 87.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.437 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 %
Inhibition of TNF-alpha-induced cell adhesion in human U937 cells assessed as reduction in cell adhesion to HT-29 cells at 1000 uM relative to control Homo sapiens 9.9 %
Inhibition of IL-6-induced cell adhesion in human U937 cells assessed as reduction in cell adhesion to HT-29 cells at 1000 uM relative to control Homo sapiens 1.7 %

Related Entries

Cross References

Resources Reference
ChEBI 6775
ChEMBL CHEMBL704
DrugBank DB00244
DrugCentral 1710
FDA SRS 4Q81I59GXC
Human Metabolome Database HMDB0014389
Guide to Pharmacology 2700
PharmGKB PA450384
PubChem 4075
SureChEMBL SCHEMBL18038934
ZINC ZINC000000001688
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