METHSCOPOLAMINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
UNII VDR09VTQ8U
EPA CompTox DTXSID0046931

Structure

InChI Key LZCOQTDXKCNBEE-IKIFYQGPSA-N
Smiles C[N+]1(C)[C@@H]2C[C@@H](OC(=O)[C@H](CO)c3ccccc3)C[C@H]1[C@@H]1O[C@@H]12
InChI
InChI=1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12-,13-,14-,15+,16-,17+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H24NO4+
Molecular Weight 318.39
AlogP 1.06
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 59.06
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 23.0
Assay Description Organism Bioactivity Reference
Compound was evaluated for its binding affinity at human muscarinic receptor m1 by displacement of [3H]-NMS radioligand using membranes in transfected chinese hamster ovarian cell None 1.8 nM
Compound was evaluated for its binding affinity at human muscarinic receptor m2 by displacement of [3H]NMS radioligand using membranes from transfected chinese hamster ovarian cell None 4.3 nM
Compound was evaluated for its binding affinity at human muscarinic receptor m3 by the displacement of [3H]NMS radioligand using membranes from transfected chinese hamster ovarian cell None 1.1 nM
Compound was evaluated for its binding affinity at human muscarinic receptor m4 by the displacement of [3H]NMS radioligand using membranes from transfected chinese hamster ovarian cell None 2.3 nM
Compound was evaluated for its binding affinity at human muscarinic receptor m5 by the displacement of [3H]-NMS radioligand using membranes from transfected chinese hamster ovarian cell None 2.3 nM
Binding affinity to human cloned muscarinic receptor M1 expressed in CHO cells Homo sapiens 0.3236 nM
Binding affinity to human cloned muscarinic receptor M2 expressed in CHO cells Homo sapiens 0.1778 nM
Binding affinity to human cloned muscarinic receptor M3 expressed in CHO cells Homo sapiens 0.1349 nM
Binding affinity to human cloned muscarinic receptor M4 expressed in CHO cells Homo sapiens 0.1413 nM
Binding affinity to human cloned muscarinic receptor M5 expressed in CHO cells Homo sapiens 0.2089 nM
Antagonist activity at muscarinic receptor M2 assessed as contraction of electrically-stimulated guinea pig left atria Cavia porcellus 0.4677 nM
Antagonist activity at muscarinic receptor M3 assessed as contraction of guinea pig ileum Cavia porcellus 0.6166 nM
Antagonist activity at putative muscarinic receptor M4 assessed as contraction of electrically-stimulated guinea pig lung strips Cavia porcellus 6.457 nM
Stimulation of disulfide bond cross-linking formation in rat M3'(3C)-Xa receptor A91C/T549C mutant expressed in african green monkey COS7 cells by scanning densitometry Rattus norvegicus 0.05 nM
Stimulation of disulfide bond cross-linking formation in rat M3'(3C)-Xa receptor F92C/F550C mutant expressed in african green monkey COS7 cells by scanning densitometry Rattus norvegicus 0.195 nM
Displacement of [3H]NMS from human cloned muscarinic M1 receptor expressed in CHO cells by scintillation counting Homo sapiens 0.3236 nM
Displacement of [3H]NMS from human cloned muscarinic M2 receptor expressed in CHO cells by scintillation counting Homo sapiens 0.1778 nM
Displacement of [3H]NMS from human cloned muscarinic M3 receptor expressed in CHO cells by scintillation counting Homo sapiens 0.1349 nM
Displacement of [3H]NMS from human cloned muscarinic M4 receptor expressed in CHO cells by scintillation counting Homo sapiens 0.1413 nM
Displacement of [3H]NMS from human cloned muscarinic M5 receptor expressed in CHO cells by scintillation counting Homo sapiens 0.2089 nM
Antagonist activity at muscarinic M2 receptor in guinea pig left atrium assessed as effect on electrically-stimulated inotropic activity after 60 mins Cavia porcellus 0.4677 nM
Antagonist activity at muscarinic M4 receptor in guinea pig lung strips assessed as effect on isotonic contraction after 60 mins Cavia porcellus 6.457 nM
Antagonist activity at muscarinic M3 receptor in guinea pig ileum assessed as effect on isotonic tension after 60 mins Cavia porcellus 0.6166 nM
Displacement of [3H]N-methylscopolamine from human muscarinic M1 receptor expressed in CHO cells after 120 mins by scintillation counting Homo sapiens 0.3236 nM
Displacement of [3H]N-methylscopolamine from human muscarinic M2 receptor expressed in CHO cells after 120 mins by scintillation counting Homo sapiens 0.1778 nM
Displacement of [3H]N-methylscopolamine from human muscarinic M3 receptor expressed in CHO cells after 120 mins by scintillation counting Homo sapiens 0.1349 nM
Displacement of [3H]N-methylscopolamine from human muscarinic M4 receptor expressed in CHO cells after 120 mins by scintillation counting Homo sapiens 0.1413 nM
Displacement of [3H]N-methylscopolamine from human muscarinic M5 receptor expressed in CHO cells after 120 mins by scintillation counting Homo sapiens 0.2089 nM
Inhibition of Atropa belladonna recombinant hycosamine 6beta-hydroxylase expressed in Escherichia coli using hyoscyamine as substrate assessed as inhibition of hydroxylated product formation at 0.1 mM after 1 hr by HPLC analysis Atropa belladonna 7.0 %
Competitive inhibition of EGFP-fused human M1 receptor N-terminal truncated at 17 residues expressed in HEK293 cells after 4 hrs by FRET assay in presence of para-LRB-AC42 Homo sapiens 0.1698 nM
Displacement of [3H]NMS from EGFP-fused human M1 receptor N-terminal truncated at 17 residues expressed in HEK293 cells after 22 hrs by liquid scintillation counting Homo sapiens 0.0955 nM
Displacement of [3H]-NMS from wild-type human muscarinic M2 receptor expressed in Flp-In-CHO cells by liquid scintillation counting Homo sapiens 0.4266 nM
Displacement of [3H]-NMS from human muscarinic M2 Y104A mutant expressed in Flp-In-CHO cells by liquid scintillation counting Homo sapiens 10.47 nM
Displacement of [3H]-NMS from human muscarinic M2 Y177Q mutant expressed in Flp-In-CHO cells by liquid scintillation counting Homo sapiens 0.7244 nM
Displacement of [3H]-NMS from human muscarinic M2 Y177Q/T423H mutant expressed in Flp-In-CHO cells by liquid scintillation counting Homo sapiens 0.3311 nM
Displacement of [3H]-NMS from human muscarinic M2 W422A mutant expressed in Flp-In-CHO cells by liquid scintillation counting Homo sapiens 0.4365 nM
Displacement of [3H]-NMS from wild-type human muscarinic M5 receptor expressed in CHO-K1 cells by liquid scintillation counting Homo sapiens 1.122 nM
Displacement of [3H]UNSW-MK259 from human muscarinic acetylcholine receptor M2 expressed in CHOK9 cells after 3 hrs by liquid scintillation counting assay Homo sapiens 0.0631 nM
Displacement of [3H]UR-AP060 from human muscarinic acetylcholine receptor M2 expressed in CHOK9 cell homogenate after 3 hrs by liquid scintillation counting assay Homo sapiens 1.202 nM
Competitive binding affinity to human muscarinic acetylcholine receptor M2 expressed in CHOK9 cells assessed as W84 pIC50 at 2 nM after 2 hrs by liquid scintillation counting assay Homo sapiens 501.19 nM
Competitive binding affinity to human muscarinic acetylcholine receptor M2 expressed in CHOK9 cells assessed as W84 pIC50 at 0.2 nM after 2 hrs by liquid scintillation counting assay Homo sapiens 398.11 nM
Competitive binding affinity to human muscarinic acetylcholine receptor M2 expressed in CHOK9 cells assessed as W84 pIC50 at 0.1 nM after 2 hrs by liquid scintillation counting assay Homo sapiens 436.52 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 16.14 %
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 -0.02 % 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 -0.02 %

Related Entries

Cross References

Resources Reference
ChEBI 135361
ChEMBL CHEMBL376897
DrugBank DB11315
DrugCentral 1757
FDA SRS VDR09VTQ8U
Human Metabolome Database HMDB0014605
PDB 3C0
SureChEMBL SCHEMBL65398
ZINC ZINC000100047524
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