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Compound Detail

CHEMBL17976

RESINIFERATOXIN
🧪 Phase III
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🧪 Phase III
C=C(C)[C@]12C[C@@H](C)[C@@]34O[C@](Cc5ccccc5)(O[C@@H]1[C@@H]3C=C(COC(=O)Cc1ccc(O)c(OC)c1)C[C@]1(O)C(=O)C(C)=C[C@@H]41)O2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL17976
Name RESINIFERATOXIN
Phase Phase III
Structure Type BOTH
InChI Key DSDNAKHZNJAGHN-MXTYGGKSSA-N

Known Names

Lopain Mtx-071 MTX-71 Neuroclastin Resiniferatoxin RTX
8
Targets
27
Activities
3
Assay Types
0
PK Parameters
20
Publications
6
Known Names
4
Indications
1
Mechanisms

Molecular Properties

628.7
MW (Da)
4.74
ALogP
9
HBA
2
HBD
120.8
PSA (Ų)
0.32
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -oxin
USAN Year 2019

Extended Properties

Molecular Formula C37H40O9
MW 628.72
Aromatic Rings 2
Heavy Atoms 46
NP-Likeness 2.44

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Vanilloid receptor agonist AGONIST Transient receptor potential cation channel subfamily V member 1 ✓ ✓

Indications

Cancer Pain Morton Neuroma Osteoarthritis, Knee Pain, Intractable

Activity Summary

EC50 13 meas. best 10.72
Ki 12 meas. best 10.7
IC50 2 meas. best 6.75

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transient receptor potential cation channel subfamily V member 1
CHEMBL4794
 EC50 10.72 9.648 0.0 5
Transient receptor potential cation channel subfamily V member 1
CHEMBL5102
 Ki 10.7 10.0357 0.0 7
Transient receptor potential cation channel subfamily V member 1
CHEMBL5102
 EC50 9.57 9.57 0.3 2
Transient receptor potential cation channel subfamily V member 1
CHEMBL4794
 Ki 9.32 8.526 0.5 5
Vanilloid receptor
CHEMBL2096684
 EC50 8.8 8.02 1.6 2
Transient receptor potential cation channel subfamily V member 1
CHEMBL5102
 IC50 6.75 6.75 180.0 1
Mus musculus
CHEMBL375
 EC50 6.04 6.04 920.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.75 5.75 1800.0 1
5637
CHEMBL612565
 IC50 4.7 4.7 19900.0 1
Human immunodeficiency virus 2
CHEMBL380
 EC50 4.65 4.65 22600.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.58 4.58 26000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Transient receptor potential cation channel subfamily V member 1 EC50 = 0.019 nM 10.72 Agonist activity at human TRPV1 expressed in HEK293 cells assessed as increase i... 19951840
Transient receptor potential cation channel subfamily V member 1 EC50 = 0.019 nM 10.72 Agonist activity at human recombinant TRPV1 expressed in human HEK293 cells 17046253
Transient receptor potential cation channel subfamily V member 1 Ki = 0.02 nM 10.7 Displacement of [3H]RTX from Vanilloid receptor in Rat spinal cord membranes 8759633
Transient receptor potential cation channel subfamily V member 1 Ki = 0.023 nM 10.64 In vitro binding affinity towards vanilloid receptor by [3H]RTX displacement. 10571146
Transient receptor potential cation channel subfamily V member 1 Ki = 0.043 nM 10.37 Displacement of [3H]RTX from rat TRV1 expressed in CHO cells by competitive bind... 21111618
Transient receptor potential cation channel subfamily V member 1 Ki = 0.0426 nM 10.37 Displacement of [3H]RTX form rat TRPV1 receptor expressed in CHO/VR1 cell system 19135377
Transient receptor potential cation channel subfamily V member 1 Ki = 0.12 nM 9.92 Binding affinity against Vanilloid receptor in dorsal Root Ganglion (DRG) membra... 8709128
Transient receptor potential cation channel subfamily V member 1 Ki = 0.13 nM 9.89 In vitro binding to Rat Vanilloid receptor 1 (VR1) expressing CHO cells compared... 12825950
Transient receptor potential cation channel subfamily V member 1 EC50 = 0.27 nM 9.57 Agonist activity at rat TRPV1 expressed in CHO cells assessed as 45Ca2+ uptake 21111618
Transient receptor potential cation channel subfamily V member 1 EC50 = 0.27 nM 9.57 Agonist activity at rat TRPV1 receptor expressed in CHO cells assessed as calciu... 19135377
Transient receptor potential cation channel subfamily V member 1 Ki = 0.48 nM 9.32 Inhibition of [3H]RTX binding to human Vanilloid receptor subtype 1 expressed in... 11934585
Transient receptor potential cation channel subfamily V member 1 EC50 = 0.92 nM 9.04 Agonist activity at human TRPV1 expressed in CHO cells assessed as 45Ca2+ uptake... 24321344
Transient receptor potential cation channel subfamily V member 1 EC50 = 0.92 nM 9.04 Agonist activity at human TRPV1 expressed in CHO cells assessed as stimulation o... 23981530
Transient receptor potential cation channel subfamily V member 1 Ki = 1.23 nM 8.91 Displacement of [3H]RTX from human TRPV1 expressed in CHO cells after 60 mins by... 24321344
Transient receptor potential cation channel subfamily V member 1 Ki = 1.23 nM 8.91 Displacement of [3H]RTX from human TRPV1 expressed in CHO cells 23981530
Vanilloid receptor EC50 = 1.6 nM 8.8 Ability to stimulate uptake of Calcium into Dorsal Root Ganglion(DRG) neurons 8709128
Transient receptor potential cation channel subfamily V member 1 EC50 = 1.9 nM 8.72 Induced [Ca2+] influx in Vanilloid receptor subtype 1 expressing HEK 293 cells 11934585
Transient receptor potential cation channel subfamily V member 1 Ki = 4.4 nM 8.36 Binding affinity against Vanilloid receptor in dorsal Root Ganglion (DRG) membra... 8709128
Transient receptor potential cation channel subfamily V member 1 Ki = 14.0 nM 7.85 Binding affinity to human recombinant TRPV1 20947352
Transient receptor potential cation channel subfamily V member 1 Ki = 23.1 nM 7.64 Displacement of [3H]RTX binding from vanilloid receptor -

Literature References

PubMed DOI Target Context # Activities
8709128 10.1021/jm960139d Transient receptor potential cation channel subfamily V member 1 6
24484240 10.1021/np400885u Transient receptor potential cation channel subfamily M member 8 6
19135377 10.1016/j.bmc.2008.11.085 Transient receptor potential cation channel subfamily V member 1 4
11934585 10.1016/s0960-894x(02)00127-0 Transient receptor potential cation channel subfamily V member 1 3
24321344 10.1016/j.bmcl.2013.10.064 Transient receptor potential cation channel subfamily V member 1 3
23981530 10.1016/j.ejmech.2013.07.042 Transient receptor potential cation channel subfamily V member 1 3
21111618 10.1016/j.bmcl.2010.11.012 Transient receptor potential cation channel subfamily V member 1 3
25970561 10.1021/acs.jnatprod.5b00073 Unchecked 3
7119808 10.1021/np50021a018 Mus musculus 2
20947352 10.1016/j.bmcl.2010.09.023 Transient receptor potential cation channel subfamily V member 1 2
8709128 10.1021/jm960139d Vanilloid receptor 2
8759633 10.1021/jm960063l Transient receptor potential cation channel subfamily V member 1 1
8759633 10.1021/jm960063l ADMET 1
17046253 10.1016/j.bmcl.2006.09.077 Transient receptor potential cation channel subfamily V member 1 1
12825950 10.1021/jm030089u Transient receptor potential cation channel subfamily V member 1 1
19135377 10.1016/j.bmc.2008.11.085 ADMET 1
36395649 10.1016/j.ejmech.2022.114893 Mus musculus 1
15139748 10.1021/jm030560j Transient receptor potential cation channel subfamily V member 1 1
10571146 10.1016/s0960-894x(99)00513-2 Vanilloid receptor 1
10571146 10.1016/s0960-894x(99)00513-2 Transient receptor potential cation channel subfamily V member 1 1

Data from ChEMBL 36 via Core Engine