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Compound Detail

CHEMBL248095

SINOMENINE
🧪 Phase III
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🧪 Phase III
COC1=C[C@@H]2[C@@H]3Cc4ccc(OC)c(O)c4[C@]2(CCN3C)CC1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL248095
Name SINOMENINE
Phase Phase III
Structure Type MOL
InChI Key INYYVPJSBIVGPH-QHRIQVFBSA-N

Known Names

Cucoline Kukoline Sinomenin Sinomenine
3
Targets
4
Activities
2
Assay Types
1
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

329.4
MW (Da)
2.02
ALogP
5
HBA
1
HBD
59.0
PSA (Ų)
0.90
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C19H23NO4
MW 329.40
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 2.12

Indications

Osteoarthritis, Knee

Activity Summary

EC50 2 meas. best 5.4
IC50 2 meas. best 4.43

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mas-related G-protein coupled receptor member X2
CHEMBL5849
 EC50 5.4 5.335 3981.1 2
K562
CHEMBL385
 IC50 4.43 4.43 37240.0 1
Entamoeba histolytica
CHEMBL612853
 IC50 4.25 4.25 56200.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 0.68 10^3/M Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mas-related G-protein coupled receptor member X2 EC50 = 3981.07 nM 5.4 Agonist activity at N-terminal Flag-tagged human MRGPRX2 receptor expressed in t... 28288109
Mas-related G-protein coupled receptor member X2 EC50 = 5370.32 nM 5.27 Agonist activity at MRGPRX2 (unknown origin) expressed in HTLA cells assessed as... 28288109
K562 IC50 = 37240.0 nM 4.43 Antiproliferative activity against human K562 cells by CCK8 assay 37939862
Entamoeba histolytica IC50 = 56200.0 nM 4.25 Antiamnesic activity against Entamoeba histolytica NIH 200 after 72 hrs by micro... 11141105

Literature References

PubMed DOI Target Context # Activities
33412412 10.1016/j.bmc.2020.115986 Unchecked 18
33412412 10.1016/j.bmc.2020.115986 MCF7 7
33412412 10.1016/j.bmc.2020.115986 MDA-MB-231 7
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 6
21530276 10.1016/j.bmc.2011.04.006 RAW264.7 5
22325804 10.1016/j.ejmech.2012.01.036 RAW264.7 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
32823004 10.1016/j.ejmech.2020.112722 Rattus norvegicus 2
34450495 10.1016/j.ejmech.2021.113791 Peritoneal macrophage 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.1007/s00044-011-9767-1 Entamoeba histolytica 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23357309 10.1016/j.ejmech.2012.12.051 NIH3T3 1
23357309 10.1016/j.ejmech.2012.12.051 Tumor necrosis factor 1
23062825 10.1016/j.bmc.2012.09.040 Acetylcholinesterase 1
22892114 10.1016/j.bmcl.2012.07.087 Unchecked 1
20097066 10.1016/j.bmcl.2010.01.007 Cyclin-dependent kinase 2 1
11141105 10.1021/np000144r KB 1
11141105 10.1021/np000144r Entamoeba histolytica 1

Data from ChEMBL 36 via Core Engine