Synonyms
Status
Molecule Category UNKNOWN
UNII I7Z38E70VF
EPA CompTox DTXSID80148292

Structure

InChI Key LWJGMYMNSNVCEM-UHFFFAOYSA-N
Smiles COc1ccc2cc(OCC3(C(=O)O)CN(C(=O)c4ccc(F)cc4)C3)ccc2c1
InChI
InChI=1S/C23H20FNO5/c1-29-19-8-4-17-11-20(9-5-16(17)10-19)30-14-23(22(27)28)12-25(13-23)21(26)15-2-6-18(24)7-3-15/h2-11H,12-14H2,1H3,(H,27,28)

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H20FNO5
Molecular Weight 409.41
AlogP 3.59
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 76.07
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 30.0
Assay Description Organism Bioactivity Reference
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 -3.79 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 19.32 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.53 %
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 0.2 % 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 -0.06 % 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 0.2 % 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 -0.06 %
GPCRScan assay: inhibition of 5-HT1A Homo sapiens -22.74 %
GPCRScan assay: inhibition of 5-HT1B Homo sapiens -11.25 %
GPCRScan assay: inhibition of 5-HT1D Homo sapiens -24.02 %
GPCRScan assay: inhibition of 5-HT1E Homo sapiens 10.97 %
GPCRScan assay: inhibition of 5-HT2A Homo sapiens 6.25 %
GPCRScan assay: inhibition of 5-HT2B Homo sapiens -0.11 %
GPCRScan assay: inhibition of 5-HT2C Homo sapiens 12.35 %
GPCRScan assay: inhibition of 5-HT3 Homo sapiens 0.08 %
GPCRScan assay: inhibition of 5-HT5A Homo sapiens -8.97 %
GPCRScan assay: inhibition of 5-HT6 Homo sapiens -6.47 %
GPCRScan assay: inhibition of 5-HT7A Homo sapiens -9.26 %
GPCRScan assay: inhibition of D1 Homo sapiens -26.64 %
GPCRScan assay: inhibition of D2 Homo sapiens -23.45 %
GPCRScan assay: inhibition of D3 Homo sapiens 32.96 %
GPCRScan assay: inhibition of D4 Homo sapiens 8.76 %
GPCRScan assay: inhibition of D5 Homo sapiens -2.51 %
GPCRScan assay: inhibition of SERT Homo sapiens -6.83 %
GPCRScan assay: inhibition of NET Homo sapiens 11.01 %
GPCRScan assay: inhibition of DAT Homo sapiens -14.46 %
GPCRScan assay: inhibition of MOR Homo sapiens 1.07 %
GPCRScan assay: inhibition of DOR Homo sapiens 5.07 %
GPCRScan assay: inhibition of KOR Homo sapiens 16.41 %
GPCRScan assay: inhibition of GABAA Rattus -1.97 %
GPCRScan assay: inhibition of H1 Homo sapiens -11.53 %
GPCRScan assay: inhibition of H2 Homo sapiens 3.0 %
GPCRScan assay: inhibition of H3 Homo sapiens -15.34 %
GPCRScan assay: inhibition of H4 Homo sapiens -17.71 %
GPCRScan assay: inhibition of Alpha1A Homo sapiens 2.52 %
GPCRScan assay: inhibition of Alpha1B Homo sapiens -11.36 %
GPCRScan assay: inhibition of Alpha2A Homo sapiens 21.8 %
GPCRScan assay: inhibition of Alpha2B Homo sapiens 9.24 %
GPCRScan assay: inhibition of Alpha2C Homo sapiens 9.72 %
GPCRScan assay: inhibition of Beta1 Homo sapiens -12.18 %
GPCRScan assay: inhibition of Beta2 Homo sapiens -17.45 %
GPCRScan assay: inhibition of M1 Homo sapiens -0.03 %
GPCRScan assay: inhibition of M2 Homo sapiens 16.71 %
GPCRScan assay: inhibition of M3 Homo sapiens 19.22 %
GPCRScan assay: inhibition of M4 Homo sapiens -18.57 %
GPCRScan assay: inhibition of M5 Homo sapiens -7.44 %
GPCRScan assay: inhibition of Beta3 Homo sapiens -19.86 %
GPCRScan assay: inhibition of GABAA/BZP Rattus 18.7 %
GPCRScan assay: inhibition of GABA/PBR Rattus -30.46 %
GPCRScan assay: inhibition of Alpha1D Homo sapiens -3.76 %
GPCRScan assay: inhibition of Sigma 2 Homo sapiens -1.29 %
GPCRScan assay: inhibition of Sigma 1 Homo sapiens 21.07 %
Inhibition of binding to PTGER2 Homo sapiens 5.0 nM
Binding assay (PTGFR) Homo sapiens 10.0 µM
Binding assay (PTGIR) Homo sapiens 10.0 µM
Binding assay (TBXA2R) Homo sapiens 10.0 µM
Binding assay (LTB4R ) Homo sapiens 4.8 µM
5-HT transporter (h) CEREP ligand profiling Homo sapiens -8.0 %
5-HT1A (h) CEREP ligand profiling Homo sapiens 6.0 %
5-HT1B CEREP ligand profiling Homo sapiens -7.0 %
5-HT1D CEREP ligand profiling None -10.0 %
5-HT2A (h) CEREP ligand profiling None 0.0 %
5-HT2A (h) (agonist site) CEREP ligand profiling Homo sapiens -15.0 %
5-HT2B (h) (agonist site/DOI) CEREP ligand profiling Homo sapiens 13.0 %
5-HT2C (h) CEREP ligand profiling Homo sapiens 8.0 %
5-HT2C (h) (agonist site) CEREP ligand profiling Homo sapiens -6.0 %
5-HT3 (h) CEREP ligand profiling Homo sapiens -6.0 %
5-HT4e (h) CEREP ligand profiling Homo sapiens -14.0 %
5-HT6 (h) CEREP ligand profiling Homo sapiens 0.0 %
5-HT7 (h) CEREP ligand profiling Homo sapiens -2.0 %
A1 (h) CEREP ligand profiling Homo sapiens -2.0 %
A2A (h) CEREP ligand profiling Homo sapiens -9.0 %
A3 (h) CEREP ligand profiling Homo sapiens -10.0 %
Abl kinase (h) CEREP ligand profiling Homo sapiens 9.0 %
ACE (h) CEREP ligand profiling Homo sapiens 14.0 %
Acetylcholinesterase (h) CEREP ligand profiling Homo sapiens 45.0 %
alpha 1 (non- selective) CEREP ligand profiling None 9.0 %
alpha 2A (h) CEREP ligand profiling Homo sapiens 26.0 %
alpha 2B (h) CEREP ligand profiling Homo sapiens 1.0 %
alpha 2C (h) CEREP ligand profiling Homo sapiens 4.0 %
AMPA CEREP ligand profiling None -13.0 %
Androgen (h) (AR) CEREP ligand profiling Homo sapiens 0.0 %
AT1 (h) CEREP ligand profiling Homo sapiens 1.0 %
ATPase (Na+/K+) CEREP ligand profiling Homo sapiens 5.0 %
beta 1 (h) CEREP ligand profiling Homo sapiens 9.0 %
beta 2 (h) CEREP ligand profiling Homo sapiens -4.0 %
beta 3 (h) CEREP ligand profiling Homo sapiens 3.0 %
Ca2+ channel (L, DHP site) CEREP ligand profiling Homo sapiens -3.0 %
Ca2+ channel (L, diltiazem site) CEREP ligand profiling Homo sapiens 6.0 %
Ca2+ channel (L, verapamil site) CEREP ligand profiling Homo sapiens -5.0 %
Ca2+ channel (N) CEREP ligand profiling Homo sapiens -7.0 %
CaMK2alpha (h) CEREP ligand profiling Homo sapiens 5.0 %
Carbonic anhydrase II (h) CEREP ligand profiling Homo sapiens 9.0 %
Caspase-3 (h) CEREP ligand profiling Homo sapiens 0.0 %
CB1 (h) CEREP ligand profiling Homo sapiens 0.0 %
CB2 (h) CEREP ligand profiling Homo sapiens 0.0 %
CCKA (h) (CCK1) CEREP ligand profiling Homo sapiens 29.0 %
CCKB (h) (CCK2) CEREP ligand profiling Homo sapiens -8.0 %
Choline transporter (h) (CHT1) CEREP ligand profiling Homo sapiens 4.0 %
Cl- channel CEREP ligand profiling None 19.0 %
COX1 (h) CEREP ligand profiling Homo sapiens -25.0 %
COX2 (h) CEREP ligand profiling Homo sapiens 2.0 %
CXCR4 (h) CEREP ligand profiling Homo sapiens 4.0 %
CYP2C19 inhibition CEREP ligand profiling None 5.0 %
CYP2C9 inhibition CEREP ligand profiling None 41.0 %
CYP2D6 inhibition CEREP ligand profiling None 18.0 %
CYP3A4 inhibition CEREP ligand profiling None 17.0 %
D1 (h) CEREP ligand profiling Homo sapiens 5.0 %
D2S (h) CEREP ligand profiling Homo sapiens -2.0 %
D2S (h) (agonist site) CEREP ligand profiling Homo sapiens -6.0 %
D3 (h) CEREP ligand profiling Homo sapiens 1.0 %
D4.4 (h) CEREP ligand profiling Homo sapiens -8.0 %
DA transporter (h) CEREP ligand profiling Homo sapiens 11.0 %
delta 2 (h) (DOP) CEREP ligand profiling Homo sapiens 0.0 %
ETA (h) CEREP ligand profiling Homo sapiens 3.0 %
ETB (h) CEREP ligand profiling Homo sapiens -1.0 %
FLT-1 kinase (h) (VEGFR1) CEREP ligand profiling Homo sapiens 9.0 %
GABAA BZD (central) CEREP ligand profiling None 10.0 %
GABA transporter CEREP ligand profiling None 14.0 %
GABAA CEREP ligand profiling None 16.0 %
GABAB (1b) (h) CEREP ligand profiling Homo sapiens -21.0 %
Ghrelin (h) (GHS) CEREP ligand profiling Homo sapiens -6.0 %
GR (h) CEREP ligand profiling Homo sapiens -1.0 %
Glycine (strychnine-insensitive) CEREP ligand profiling None 11.0 %
H1 (h) CEREP ligand profiling Homo sapiens 0.0 %
H2 (h) CEREP ligand profiling Homo sapiens 3.0 %
H3 (h) CEREP ligand profiling Homo sapiens 10.0 %
H4 (h) CEREP ligand profiling Homo sapiens -4.0 %
I1 CEREP ligand profiling None -14.0 %
Kainate CEREP ligand profiling None -15.0 %
kappa (KOP) CEREP ligand profiling Homo sapiens 46.0 %
LTB4 (h) (BLT1) CEREP ligand profiling Homo sapiens 51.0 %
LTD4 (h) (CysLT1) CEREP ligand profiling Homo sapiens 2.0 %
Lyn kinase (h) CEREP ligand profiling Homo sapiens 2.0 %
M1 (h) CEREP ligand profiling Homo sapiens 9.0 %
M2 (h) CEREP ligand profiling Homo sapiens 1.0 %
M3 (h) CEREP ligand profiling Homo sapiens 1.0 %
M4 (h) CEREP ligand profiling Homo sapiens 0.0 %
M5 (h) CEREP ligand profiling Homo sapiens 1.0 %
MAO-A CEREP ligand profiling None 3.0 %
MC1 CEREP ligand profiling None 6.0 %
MC3 (h) CEREP ligand profiling Homo sapiens -11.0 %
MC4 (h) CEREP ligand profiling Homo sapiens 8.0 %
MCH1 (h) CEREP ligand profiling Homo sapiens -13.0 %
ML1 CEREP ligand profiling None -3.0 %
ML2 (MT3) CEREP ligand profiling None 93.0 % ML2 (MT3) CEREP ligand profiling None 530.0 nM ML2 (MT3) CEREP ligand profiling None 520.0 nM
MMP-9 (h) CEREP ligand profiling Homo sapiens 10.0 %
Motilin (h) CEREP ligand profiling Homo sapiens -5.0 %
mu (h) (MOP) (agonist site) CEREP ligand profiling Homo sapiens -7.0 %
N (muscle-type) (h) CEREP ligand profiling Homo sapiens -10.0 %
N (neuronal) (alpha -BGTX-insensitive) (alpha 4 beta 2) CEREP ligand profiling None -10.0 %
Na+ channel (site 2) CEREP ligand profiling None 9.0 %
NE transporter (h) CEREP ligand profiling Homo sapiens -2.0 %
NK1 (h) CEREP ligand profiling Homo sapiens 3.0 %
NK2 (h) CEREP ligand profiling Homo sapiens 0.0 %
NMDA CEREP ligand profiling None 1.0 %
p38 alpha kinase (h) CEREP ligand profiling Homo sapiens -1.0 %
PCP CEREP ligand profiling None -6.0 %
PDE11 (h) CEREP ligand profiling Homo sapiens 14.0 %
PDE2 (h) CEREP ligand profiling Homo sapiens 5.0 %
PDE3 (h) CEREP ligand profiling Homo sapiens 78.0 %
PDE4 (h) CEREP ligand profiling Homo sapiens 8.0 %
PDE5 (h) CEREP ligand profiling Homo sapiens 6.0 %
PDE6 CEREP ligand profiling None 3.0 %
PPAR gamma (h) CEREP ligand profiling Homo sapiens 14.0 %
Rolipram CEREP ligand profiling None 3.0 %
sigma (non-selective) CEREP ligand profiling None 0.0 %
SK+Ca channel CEREP ligand profiling None -1.0 %
sst4 (h) CEREP ligand profiling Homo sapiens 0.0 %
TH CEREP ligand profiling None -10.0 %
TNF-alpha (h) CEREP ligand profiling Homo sapiens -1.0 %
TXA2/P GH2 (h)(TP) CEREP ligand profiling Homo sapiens 0.0 %
UT1 (h) CEREP ligand profiling Homo sapiens 14.0 %
V1a (h) CEREP ligand profiling Homo sapiens -3.0 %
V2 (h) CEREP ligand profiling Homo sapiens -1.0 %
VIP1 (h) (VPAC1) CEREP ligand profiling Homo sapiens -13.0 %
Y1 (h) CEREP ligand profiling Homo sapiens 1.0 %
ZAP70 kinase (h) CEREP ligand profiling Homo sapiens 9.0 %

Cross References

Resources Reference
ChEMBL CHEMBL3286797
DrugBank DB12024
FDA SRS I7Z38E70VF
Guide to Pharmacology 5817
PubChem 25114442
SureChEMBL SCHEMBL3632622
ZINC ZINC000095644391