Synonyms
Status
Molecule Category Free-form
ATC N05AE04
UNII 6UKA5VEJ6X
EPA CompTox DTXSID4023753

Structure

InChI Key MVWVFYHBGMAFLY-UHFFFAOYSA-N
Smiles O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1
InChI
InChI=1S/C21H21ClN4OS/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27)

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H21ClN4OS
Molecular Weight 412.95
AlogP 3.81
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 48.47
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 28.0
Assay Description Organism Bioactivity Reference
Binding affinity towards human 5-hydroxytryptamine 1 receptor None 37.0 nM
Binding affinity towards human serotonin 5-hydroxytryptamine 2A receptor None 0.3 nM
Binding affinity for human 5-hydroxytryptamine 2A receptor Homo sapiens 0.25 nM
Displacement of [3H]-ketanserin from rat brain 5-hydroxytryptamine 2A receptor Rattus norvegicus 0.4169 nM
Relative binding affinity for D2 receptor and 5-hydroxytryptamine 2A receptor, ratio of Ki Rattus norvegicus 0.42 nM
Binding affinity towards human serotonin 5-hydroxytryptamine 2C receptor None 13.0 nM
Binding affinity towards human 5-hydroxytryptamine 2C receptor None 0.55 nM
Displacement of [3H]prazosin from Alpha-1 adrenergic receptor in rat brain Rattus norvegicus 11.0 nM
Displacement of [3H]prazosin from rat brain Alpha-1 adrenergic receptor Rattus norvegicus 10.47 nM
Binding affinity towards human alpha-1 adrenergic receptor None 12.0 nM
Binding affinity towards human alpha-1 adrenergic receptor None 1.9 nM
Binding affinity towards human alpha-2 adrenergic receptor None 390.0 nM
Binding affinity towards human alpha-2 adrenergic receptor None 390.0 nM
Binding affinity towards human dopamine-4.2 receptor None 39.0 nM
Binding affinity towards human Dopamine receptor D2 None 9.7 nM
Binding affinity towards human D2 dopamine receptor. None 2.8 nM
Binding affinity against dopamine receptor D1 None 9.5 nM
Binding affinity towards human Dopamine receptor D1 None 330.0 nM
Binding affinity towards human dopamine receptor D4 None 39.0 nM
Displacement of [3H]NPA from rat brain Dopamine receptor D2 Rattus norvegicus 4.786 nM
Binding affinity towards human dopamine receptor D3 None 10.0 nM
Displacement of [3H]NPA from rat brain Dopamine receptor D2 Rattus norvegicus 4.8 nM
Binding affinity towards human Dopamine receptor D3 None 7.5 nM
Binding affinity towards human H1 receptor None 510.0 nM
Binding affinity towards human histamine H1 receptor None 5.3 nM
K+ channel blocking activity in human embryonic kidney cells expressing HERG Kv11.1 Homo sapiens 152.0 nM
Inhibitory concentration against potassium channel HERG None 120.23 nM
Inhibition of partially open human voltage-gated potassium channel subunit Kv11.1 (ERG K+ channel) Homo sapiens 151.36 nM
Inhibitory concentration against dopamine receptor D2 Homo sapiens 5.0 nM
Inhibitory concentration against alpha adrenergic receptor Homo sapiens 11.0 nM
Inhibitory concentration against 5-hydroxytryptamine 2 receptor Homo sapiens 0.42 nM
Displacement of [3H]spiperone from human dopamine D2 receptor short form expressed in CHO cells Homo sapiens 12.59 nM
Displacement of [3H]spiperone from human dopamine D3 receptor expressed in CHO cells Homo sapiens 6.31 nM
Displacement of [3H]spiperone from human dopamine D4.4 receptor expressed in CHO cells Homo sapiens 50.12 nM
Displacement of [3H]8-OH-DPAT from human 5HT1A receptor expressed in CHO cells Homo sapiens 1.585 nM
Displacement of [3H]ketanserin from human 5HT2A receptor expressed in CHO cells Homo sapiens 0.631 nM
Displacement of [3H]LSD from 5HT2B receptor expressed in CHO cells Homo sapiens 1.585 nM
Displacement of [3H]mesulergine from 5HT2C receptor expressed in CHO cells Homo sapiens 1.259 nM
Displacement of [3H]LSD from human 5HT6 receptor expressed in HEK293 cells Homo sapiens 63.1 nM
Displacement of [3H]LSD from human 5HT7 receptor expressed in CHO cells Homo sapiens 5.012 nM
Displacement of [3H]BLR-43694 from human 5HT3 receptor expressed in HEK293 cells Homo sapiens 398.11 nM
Displacement of [3H]paraxetine from human 5HT transporter expressed in HEK293 cells Homo sapiens 79.43 nM
Displacement of [3H]prazosin from adrenergic alpha1 receptor in rat cerebral cortex Rattus norvegicus 7.943 nM
Displacement of [3H]RX 821002 from adrenergic alpha-2 receptor in rat cerebral cortex Rattus norvegicus 501.19 nM
Displacement of [3H]pyrilamine from histaminergic H1 receptor guinea pig cerebellum Cavia porcellus 15.85 nM
Displacement of [3H]spiperone from human D2L receptor expressed in CHO cells Homo sapiens 5.0 nM
Displacement of [3H]ketanserin from human 5HT2A receptor expressed in Swiss 3T3 cells Homo sapiens 0.08 nM
Displacement of [3H]8OHDPAT from human 5HT1A receptor Homo sapiens 4.0 nM
Displacement of [3H]prazosin from rat adrenergic alpha1A receptor expressed in fibroblast cells Rattus norvegicus 0.5 nM
Displacement of [3H]mepyramine from H1R in rat brain Rattus norvegicus 150.0 nM
Binding affinity to human cloned 5HT6 receptor Homo sapiens 76.0 nM
Binding affinity to human cloned dopamine D1 receptor Homo sapiens 130.0 nM
Binding affinity to human cloned dopamine D2 receptor Homo sapiens 3.1 nM
Binding affinity to human cloned dopamine D3 receptor Homo sapiens 7.2 nM
Binding affinity to human cloned dopamine D4 receptor Homo sapiens 32.0 nM
Binding affinity to human cloned 5HT2C receptor Homo sapiens 0.72 nM
Binding affinity to human cloned histamine H1 receptor Homo sapiens 47.0 nM
Binding affinity to human cloned 5HT1A receptor Homo sapiens 2.5 nM
Binding affinity to human cloned 5HT2A receptor Homo sapiens 0.39 nM
Binding affinity to rat NET Rattus norvegicus 48.0 nM
Binding affinity to human SERT Homo sapiens 53.0 nM
Inhibition of human ERG channel Homo sapiens 125.0 nM Inhibition of human ERG channel Homo sapiens 125.0 nM
Inhibition of human ERG expressed in CHO cells by whole cell patch clamp technique Homo sapiens 120.23 nM
Inhibition of human ERG in MCF7 cells Homo sapiens 151.36 nM
Inhibition of human FAAH at 1 uM Homo sapiens -5.07 %
Inhibition of human ERG Homo sapiens 125.89 nM
Displacement of [3H]mesulergine from human 5HT2C receptor in human tsA201 cells Homo sapiens 13.0 nM
Displacement of [3H]5-LSD from human 5HT6 receptor expressed in human HeLa cells Homo sapiens 61.0 nM
Inhibition of norA-mediated ethidium bromide efflux in Staphylococcus aureus SA-1199B harboring grlA A116E mutant at 50 uM after 5 mins by fluorometric analysis Staphylococcus aureus 86.6 %
Inhibition of human recombinant MDR1 expressed in mouse L5178Y cells assessed as inhibition of rhodamine-123 efflux at 10'-4 M preincubated for 10 mins measured after 20 mins by FACS analysis Homo sapiens 19.0 %
Displacement of [3H]methylspiperone from human low affinity Dopamine D2S receptor by competition binding assay Homo sapiens 8.5 nM
Binding affinity to adrenergic alpha1 receptor (unknown origin) by radioligand binding assay Homo sapiens 11.0 nM
Binding affinity to 5HT7 receptor (unknown origin) by radioligand binding assay Homo sapiens 6.0 nM
Binding affinity to 5HT6 receptor (unknown origin) by radioligand binding assay Homo sapiens 61.0 nM
Binding affinity to 5HT2C receptor (unknown origin) by radioligand binding assay Homo sapiens 1.3 nM
Binding affinity to dopamine D3 receptor (unknown origin) by radioligand binding assay Homo sapiens 7.2 nM
Binding affinity to 5HT2A receptor (unknown origin) by radioligand binding assay Homo sapiens 0.4 nM
Binding affinity to dopamine D2 receptor (unknown origin) by radioligand binding assay Homo sapiens 4.8 nM
Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1 Receptors. Homo sapiens 0.28 nM
Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1 Receptors. Homo sapiens 112.0 nM
Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1 Receptors. Homo sapiens 10.0 nM
Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1 Receptors. Homo sapiens 15.0 nM
Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1 Receptors. Homo sapiens 5.0 nM
Binding Assay: Binding assay using 5-HT2A, Dopamine D2, SERT, αA1, 5-HT2C and H1 Receptors. Homo sapiens 6.0 nM
Displacement of [3H]-Raclopride from D2L receptor (unknown origin) Homo sapiens 2.1 nM
Displacement of [3H]-ketanserin from human 5-HT2AR expressed in CHO-K1 cell membranes after 1.5 hrs by microbeta counting method Homo sapiens 1.7 nM
Displacement of [3H]-LSD from human 5-HT6R expressed in HEK293 cell membranes after 1 hr at 37 degC by microbeta counting method Homo sapiens 20.0 nM
Displacement of [3H]-8-OH-DPAT from human 5-HT1AR expressed in HEK293 cell membranes after 1 hr by microbeta counting method Homo sapiens 2.0 nM
Displacement of [3H]-5-CT from human 5-HT7R expressed in HEK293 cell membranes after 1 hr at 37 degC by microbeta counting method Homo sapiens 5.0 nM
Displacement of [3H]-raclopride from human D2LR expressed in HEK293 cell membranes after 1 hr at 37 degC by microbeta counting method Homo sapiens 0.8 nM
Displacement of [3H]-raclopride from human D2R expressed in HEK293 cells after 1 hr by microbeta plate reader analysis Homo sapiens 2.1 nM
Displacement of [3H]-methylspiperone from human D2 long receptor expressed in HEK293 cells measured after 1 hr by liquid scintillation counter method Homo sapiens 0.8511 nM Displacement of [3H]-methylspiperone from human D2 long receptor expressed in HEK293 cells measured after 1 hr by liquid scintillation counter method Homo sapiens 0.9 nM
Displacement of [3H] raclopride from human recombinant D2L receptor expressed in HEK293 cells measured after 1 hr by microbeta scintillation counting method Homo sapiens 0.9 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.21 %
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 -0.05 % 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 -0.05 %
Binding affinity to H1 histamine receptor (unknown origin) Homo sapiens 50.0 nM
Binding affinity to adrenergic alpha1 receptor (unknown origin) Homo sapiens 11.0 nM

Cross References

Resources Reference
ChEBI 10119
ChEMBL CHEMBL708
DrugBank DB00246
DrugCentral 2865
FDA SRS 6UKA5VEJ6X
Human Metabolome Database HMDB0014391
Guide to Pharmacology 59
KEGG C07568
PharmGKB PA451974
PubChem 60854
SureChEMBL SCHEMBL28028
ZINC ZINC000000538550