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Compound Detail

CHEMBL182120

VOACANGINE
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CC[C@H]1C[C@@H]2CN3CCc4c([nH]c5ccc(OC)cc45)[C@](C(=O)OC)(C2)[C@H]13
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL182120
Name VOACANGINE
Phase Preclinical
Structure Type MOL
InChI Key MMAYTCMMKJYIAM-RUGRQLENSA-N
5
Targets
12
Activities
3
Assay Types
0
PK Parameters
19
Publications
0
Known Names

Molecular Properties

368.5
MW (Da)
3.26
ALogP
4
HBA
1
HBD
54.6
PSA (Ų)
0.85
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C22H28N2O3
MW 368.48
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness 1.42

Activity Summary

IC50 8 meas. best 5.36
EC50 2 meas. best 5.1
Kd 2 meas. best 5.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Acetylcholinesterase
CHEMBL4078
 IC50 5.36 5.36 4400.0 1
Transient receptor potential cation channel subfamily M member 8
CHEMBL3108632
 IC50 5.16 5.0867 7000.0 3
Transient receptor potential cation channel subfamily M member 8
CHEMBL3108632
 Kd 5.1 5.1 7943.3 1
Transient receptor potential cation channel subfamily A member 1
CHEMBL6007
 EC50 5.1 5.1 8000.0 2
Unchecked
CHEMBL612545
 IC50 4.94 4.94 11500.0 1
Transient receptor potential cation channel subfamily V member 1
CHEMBL4794
 Kd 4.7 4.7 19952.6 1
Transient receptor potential cation channel subfamily V member 1
CHEMBL4794
 IC50 4.62 4.48 24000.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Acetylcholinesterase IC50 = 4400.0 nM 5.36 Inhibition of electric eel AChE by Ellman's method 20850311
Transient receptor potential cation channel subfamily M member 8 IC50 = 7000.0 nM 5.16 Antagonist activity against mouse TRPM8 expressed in T-REx HEK cells assessed as... 25052206
Transient receptor potential cation channel subfamily A member 1 EC50 = 8000.0 nM 5.1 Agonist activity at TRPA1 isolated from human W138 cells expressed in HEK293T ce... 24484240
Transient receptor potential cation channel subfamily A member 1 EC50 = 8000.0 nM 5.1 Agonist activity at human TRPA1 expressed in T-REx HEK cells assessed as increas... 25052206
Transient receptor potential cation channel subfamily M member 8 Kd = 7943.28 nM 5.1 Competitive antagonist at TRPM8 isolated from mouse dorsal root ganglion cells e... 24484240
Transient receptor potential cation channel subfamily M member 8 IC50 = 9000.0 nM 5.05 Antagonist at TRPM8 isolated from mouse dorsal root ganglion cells expressed in ... 24484240
Transient receptor potential cation channel subfamily M member 8 IC50 = 9000.0 nM 5.05 Antagonist activity against mouse TRPM8 expressed in T-REx HEK cells assessed as... 25052206
Unchecked IC50 = 11500.0 nM 4.94 Inhibition of Wnt/beta-catenin in human STF/293 cells assessed as inhibition of ... 26231157
Transient receptor potential cation channel subfamily V member 1 Kd = 19952.62 nM 4.7 Competitive antagonist activity at human brain TRPV1 expressed in HEK293T cells ... 24484240
Transient receptor potential cation channel subfamily V member 1 IC50 = 24000.0 nM 4.62 Antagonist activity at human brain TRPV1 expressed in HEK293T cells assessed as ... 24484240
Transient receptor potential cation channel subfamily V member 1 IC50 = 30000.0 nM 4.52 Antagonist activity against human TRPV1 expressed in T-REx HEK cells assessed as... 25052206
Transient receptor potential cation channel subfamily V member 1 IC50 = 50000.0 nM 4.3 Antagonist activity at human brain TRPV1 expressed in HEK293T cells assessed as ... 24484240

Literature References

PubMed DOI Target Context # Activities
24484240 10.1021/np400885u Transient receptor potential cation channel subfamily M member 8 23
24484240 10.1021/np400885u Transient receptor potential cation channel subfamily V member 1 12
24484240 10.1021/np400885u Transient receptor potential cation channel subfamily A member 1 10
25052206 10.1021/np500235b Transient receptor potential cation channel subfamily M member 8 5
25052206 10.1021/np500235b Transient receptor potential cation channel subfamily A member 1 4
25052206 10.1021/np500235b Transient receptor potential cation channel subfamily V member 1 3
15357977 10.1016/j.bmcl.2004.06.074 KB 2
24484240 10.1021/np400885u Transient receptor potential cation channel subfamily V member 3 2
24484240 10.1021/np400885u Transient receptor potential cation channel subfamily V member 2 2
26231157 10.1016/j.bmcl.2015.07.036 HEK-293T 2
26231157 10.1016/j.bmcl.2015.07.036 Unchecked 2
26231157 10.1016/j.bmcl.2015.07.036 NON-PROTEIN TARGET 1
26231157 10.1016/j.bmcl.2015.07.036 HCT-116 1
26231157 10.1016/j.bmcl.2015.07.036 SW480 1
26231157 10.1016/j.bmcl.2015.07.036 RKO 1
26231157 10.1016/j.bmcl.2015.07.036 HEK293 1
25052206 10.1021/np500235b ADMET 1
20850311 10.1016/j.bmcl.2010.08.123 Acetylcholinesterase 1
12713407 10.1021/np020548e A2780 1

Data from ChEMBL 36 via Core Engine