RAMATROBAN

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Synonyms
Status
Molecule Category UNKNOWN
UNII P1ALI72U6C
EPA CompTox DTXSID1046685

Structure

InChI Key LDXDSHIEDAPSSA-OAHLLOKOSA-N
Smiles O=C(O)CCn1c2c(c3ccccc31)C[C@H](NS(=O)(=O)c1ccc(F)cc1)CC2
InChI
InChI=1S/C21H21FN2O4S/c22-14-5-8-16(9-6-14)29(27,28)23-15-7-10-20-18(13-15)17-3-1-2-4-19(17)24(20)12-11-21(25)26/h1-6,8-9,15,23H,7,10-13H2,(H,25,26)/t15-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H21FN2O4S
Molecular Weight 416.47
AlogP 3.09
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 88.4
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
G protein-coupled receptor 44 antagonist ANTAGONIST PubMed PubMed
Protein: Thromboxane A2 receptor
Description: Thromboxane A2 receptor
Organism : Homo sapiens
P21731 ENSG00000006638
Protein: G protein-coupled receptor 44
Description: Prostaglandin D2 receptor 2
Organism : Homo sapiens
Q9Y5Y4 ENSG00000183134
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 15000 - - -
Enzyme Transferase
- - - - 0
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Prostanoid receptor
- 21-754 - 4-340 98
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 62400 - - -
Assay Description Organism Bioactivity Reference
Compound was tested for inhibition of U-46,619 induced aggregation of human platelets Homo sapiens 380.0 nM
Anti-platelet activity was measured by studying their antagonist effects on human platelets aggregated with collagen Homo sapiens 50.0 nM
Compound was tested for inhibition of U-46,619 induced contraction of isolated rabbit saphenous vein Oryctolagus cuniculus 12.59 nM
Inhibition of [3H]SQ-29,548 binding to human Thromboxane A2 receptor Homo sapiens 4.5 nM
Inhibition of [3H]PGD-2 binding to human chemoattractant receptor-homologous molecule expressed on Th2 cells (CRTH2) Homo sapiens 4.3 nM
Inhibitory activity for binding of PGD-2 in hTP binding assay using HEK293 cell membranes None 18.0 nM
Inhibitory activity for binding of PGD-2 to CRTH-2 in hCRTH-2 binding assay using HEK293 cell membranes Homo sapiens 290.0 nM
Inhibitory activity for PGD2-mediated receptor activation in a fluorescence assay that measures changes in intracellular calcium Homo sapiens 290.0 nM
Inhibitory concentration for PGD2-mediated receptor activation in a fluorescence assay that measures changes in intracellular calcium Homo sapiens 340.0 nM
Inhibition of beta-arrestin translocation at human Thromboxane A2 receptor in BRET assay Homo sapiens 8.4 nM
Inhibition of U-46,619-induced inositol phosphate accumulation at human Thromboxane A2 receptor Homo sapiens 9.6 nM
Inhibition of PGD2-induced inositol phosphate formation at human chemoattractant receptor-homologous molecule expressed on TH2 cells Homo sapiens 29.0 nM
Inhibition of beta-arrestin translocation at human chemoattractant receptor-homologous molecule expressed on TH2 cells in BRET assay Homo sapiens 28.0 nM
Percentage inhibition for binding of PGD-2 in hTP binding assay using HEK293 cell membranes Homo sapiens 98.0 %
Antagonist activity at human CRTH2 receptor assessed as inhibition of DK-PGD2-induced eosinophil chemotaxis Homo sapiens 169.0 nM
Displacement of [3H]PGD2 from human prostaglandin D2 receptor Homo sapiens 311.0 nM
Displacement of [3H]PGD2 from human prostaglandin D2 receptor in presence of human serum albumin Homo sapiens 754.0 nM
Displacement of [3H]SQ-29548 from thromboxane receptor in human platelet membrane Homo sapiens 14.0 nM
Displacement of [3H]PGD2 from human CRTh2 receptor expressed in CHO cells Homo sapiens 73.0 nM
Antagonist activity against CRTh2 receptor in human eosinophils assessed as cell shape change Homo sapiens 21.0 nM
Antagonist activity against human CRTh2 receptor expressed in CHO cells assessed as effect on cAMP accumulation Homo sapiens 210.0 nM
Antagonist activity against CRTh2 receptor in human whole blood assessed as eosinophil shape change Homo sapiens 195.0 nM
Inhibition of human H-PGDS expressed in Escherichia coli BL21 assessed as rate of glutathione-chloro-dinitro benzene conjugation at 50 uM Homo sapiens 0.0 %
Binding affinity to human recombinant CRTH2 receptor by cell based radioligand equilibrium competition assay Homo sapiens 137.0 nM
Binding affinity to thromboxane receptor None 0.58 nM
Displacement of [3H]PGD2 from human CRTh2 receptor expressed in HEK293 cells after 2 hrs by scintillation proximity assay Homo sapiens 77.0 nM
Antagonist activity against human CRTh2 receptor expressed in CHO cells assessed as inhibition of PGD2-mediated Ca2+ flux Homo sapiens 461.0 nM
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 -6.84 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 14.34 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.5 %
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 0.34 % 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 -0.23 % 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 -0.23 % 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 0.34 %

Related Entries

Cross References

Resources Reference
ChEBI 32087
ChEMBL CHEMBL361812
DrugBank DB13036
DrugCentral 2354
FDA SRS P1ALI72U6C
Guide to Pharmacology 1911
PDB A8X
PubChem 123879
SureChEMBL SCHEMBL29030
ZINC ZINC000003798772
CONTENTS