Compound Detail

CHEMBL85139

RUTAECARPINE

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O=c1c2ccccc2nc2n1CCc1c-2[nH]c2ccccc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL85139
Name	RUTAECARPINE
Phase	Preclinical
Structure Type	MOL
InChI Key	ACVGWSKVRYFWRP-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

287.3

MW (Da)

3.10

ALogP

HBA

HBD

50.7

PSA (Å²)

0.54

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula	C18H13N3O
MW	287.32
Aromatic Rings	4
Heavy Atoms	22
NP-Likeness	-0.06

Activity Summary

IC50 24 meas. best 8.52

EC50 7 meas. best 7.53

Ki 1 meas.

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
ADMET CHEMBL612558	IC50	8.52	8.205	3.0	2
Cytochrome P450 1A2 CHEMBL3356	IC50	7.66	7.66	22.0	1
Aorta CHEMBL613606	EC50	7.53	6.392	29.7	5
Cytochrome P450 1B1 CHEMBL4878	IC50	7.26	7.26	55.0	2
Cytochrome P450 1A1 CHEMBL2231	IC50	6.58	6.58	260.0	1
Prostaglandin G/H synthase 2 CHEMBL230	IC50	6.55	6.535	280.0	2
Histone deacetylase 6 CHEMBL1865	IC50	6.14	6.14	731.9	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	IC50	5.91	5.91	1230.0	1
Transient receptor potential cation channel subfamily V member 1 CHEMBL5102	EC50	5.69	5.69	2060.0	1
Unchecked CHEMBL612545	IC50	5.37	5.37	4300.0	1
LS174T CHEMBL614097	IC50	5.21	5.21	6100.0	1
Prostaglandin G/H synthase 1 CHEMBL221	IC50	5.06	5.06	8700.0	2
Plasmodium falciparum CHEMBL364	IC50	5.0	5.0	10000.0	1
HUVEC CHEMBL613979	IC50	4.78	4.78	16540.0	1
SMMC-7721 CHEMBL613831	IC50	4.72	4.72	18900.0	1
Danio rerio CHEMBL613963	IC50	4.59	4.59	25490.0	1
HeLa CHEMBL399	IC50	4.58	4.58	26000.0	1
HeLa CHEMBL399	EC50	4.58	4.58	26100.0	1
HCT-116 CHEMBL394	IC50	4.51	4.51	31100.0	1
P388 CHEMBL389	IC50	4.43	4.43	36800.0	1
MCF7 CHEMBL387	IC50	4.13	4.13	74500.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ka	1.0	uM	Homo sapiens
Ka	1.0	uM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
ADMET	IC50	=	3.0	nM	8.52	Ratio for inhibition of Cytochrome P450 1B1 to that of Cytochrome P450 1A2	12852960
ADMET	IC50	=	13.0	nM	7.89	Ratio for inhibition of Cytochrome P450 1A1 to that of Cytochrome P450 1A2	12852960
Cytochrome P450 1A2	IC50	=	22.0	nM	7.66	Inhibition of Cytochrome P450 1A2 enzyme in bacterial membrane expressing human ...	12852960
Aorta	EC50	=	29.7	nM	7.53	Vasodilating activity in Sprague-Dawley rat aortic rings assessed as reduction i...	30818175
Cytochrome P450 1B1	IC50	=	55.0	nM	7.26	Inhibition of human CYP1B1 expressed in Escherichia coli	28458135
Cytochrome P450 1B1	IC50	=	55.0	nM	7.26	Inhibition of Cytochrome P450 1B1 enzyme in bacterial membrane expressing human ...	12852960
Aorta	EC50	=	156.0	nM	6.81	Vasodilating activity in Sprague-Dawley rat aortic rings assessed as reduction i...	30818175
Cytochrome P450 1A1	IC50	=	260.0	nM	6.58	Inhibition of Cytochrome P450 1A1 enzyme in bacterial membrane expressing human ...	12852960
Prostaglandin G/H synthase 2	IC50	=	280.0	nM	6.55	Inhibition of COX2 in BMMC cells assessed as PGD2 generation	23146282
Prostaglandin G/H synthase 2	IC50	=	300.0	nM	6.52	Inhibition of COX2	16038536
Histone deacetylase 6	IC50	=	731.9	nM	6.14	Determination of IC50 values for inhibition of enzymatic assay of human HDAC6 wi...	-
Aorta	EC50	=	1050.0	nM	5.98	Vasodilatory activity in Sprague-Dawley rat endothelium-intact thoracic aortic r...	8699182
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1230.0	nM	5.91	Inhibition of PDE5A (unknown origin)	32171616
Aorta	EC50	=	1330.0	nM	5.88	Vasodilative activity against KCl-precontracted Sprague-Dawley rat thoracic aort...	19254847
Aorta	EC50	=	1750.0	nM	5.76	Vasodilatory activity in Sprague-Dawley rat endothelium-denuded thoracic aortic ...	8699182
Transient receptor potential cation channel subfamily V member 1	EC50	=	2060.0	nM	5.69	Agonist activity at rat TRPV1 channel expressed in HEK293 cells assessed as indu...	27159637
Unchecked	IC50	=	4300.0	nM	5.37	Inhibition of Wnt/beta-catenin transactivation signalling in HEK293 cells transf...	35544614
LS174T	IC50	=	6100.0	nM	5.21	Antiproliferative activity against human LS174T cells harboring beta-catenin mut...	35544614
Prostaglandin G/H synthase 1	IC50	=	8700.0	nM	5.06	Inhibition of COX1	16038536
Prostaglandin G/H synthase 1	IC50	=	8700.0	nM	5.06	Inhibition of COX1 in BMMC cells assessed as PGD2 generation	23146282

Literature References

PubMed	DOI	Target Context	# Activities
35544614	10.1021/acs.jnatprod.2c00224	LS174T	50
35544614	10.1021/acs.jnatprod.2c00224	Unchecked	19
27159637	10.1021/acs.jnatprod.5b00599	Transient receptor potential cation channel subfamily V member 1	12
28958621	10.1016/j.bmcl.2017.08.045	No relevant target	6
8699182	10.1021/np960161+	Aorta	6
30818175	10.1016/j.ejmech.2019.02.037	Aorta	4
-	10.6019/CHEMBL4808148	Histone deacetylase 6	4
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
19254847	10.1016/j.bmc.2009.02.015	Aorta	2
35544614	10.1021/acs.jnatprod.2c00224	ADMET	2
38897138	10.1016/j.bmc.2024.117799	MCF-10A	2
12852960	10.1016/s0960-894x(03)00469-4	ADMET	2
36375335	10.1016/j.ejmech.2022.114915	HT-29	2
16248836	10.2174/138920005774330639	Cytochrome P450 3A4	2
36375335	10.1016/j.ejmech.2022.114915	MCF7	2
22185196	10.1021/jm201328e	Nucleic Acid	2
38897138	10.1016/j.bmc.2024.117799	ADMET	1
-	10.1021/np960678l	5-hydroxytryptamine receptor 1A	1
12852960	10.1016/s0960-894x(03)00469-4	Cytochrome P450 1A2	1
12852960	10.1016/s0960-894x(03)00469-4	Cytochrome P450 1A1	1

Data from ChEMBL 36 via Core Engine