Compound Detail

CHEMBL364713

NOSCAPINE

🧪 Phase II

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🧪 Phase II

COc1ccc2c(c1OC)C(=O)O[C@@H]2[C@H]1c2c(cc3c(c2OC)OCO3)CCN1C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL364713
Name	NOSCAPINE
Phase	Phase II
Structure Type	MOL
InChI Key	AKNNEGZIBPJZJG-MSOLQXFVSA-N
Therapeutic	✓ Yes

Known Names

(-)-.alpha.-narcotine (-)-narcotine Methoxyhydrastine Narcotinum Noscapina Noscapine Noscapinum NSC-5366

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

413.4

MW (Da)

2.88

ALogP

HBA

HBD

75.7

PSA (Å²)

0.71

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem

-pine

Extended Properties

Molecular Formula	C22H23NO7
MW	413.43
Aromatic Rings	2
Heavy Atoms	30
NP-Likeness	1.34

Indications

Cough Leukemia, Lymphocytic, Chronic, B-Cell Multiple Myeloma

ATC Classification

R05DA07

noscapine

Level 1: RESPIRATORY SYSTEM

Level 2: COUGH AND COLD PREPARATIONS

Activity Summary

IC50 32 meas. best 6.4

EC50 3 meas. best 4.74

Kd 3 meas. best 6.24

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Cytochrome P450 2C19 CHEMBL3622	IC50	6.4	6.4	400.3	1
Tubulin beta CHEMBL3832942	Kd	6.24	6.24	579.0	1
Tubulin CHEMBL2095182	Kd	5.73	5.73	1860.0	1
Solute carrier family 22 member 2 CHEMBL1743122	IC50	5.58	5.58	2600.0	1
Cytochrome P450 2C9 CHEMBL3397	IC50	5.09	5.09	8177.3	1
CCRF-CEM CHEMBL382	IC50	4.84	4.84	14500.0	1
NCI/ADR-RES CHEMBL613829	IC50	4.76	4.76	17400.0	1
HeLa CHEMBL399	EC50	4.74	4.74	18400.0	1
MCF7 CHEMBL387	IC50	4.73	4.4117	18800.0	6
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.7	4.3525	20000.0	4
HeLa CHEMBL399	IC50	4.62	4.61	24000.0	4
A549 CHEMBL392	EC50	4.6	4.6	25000.0	1
Multidrug and toxin extrusion protein 1 CHEMBL1743126	IC50	4.46	4.46	34500.0	1
Unchecked CHEMBL612545	IC50	4.41	4.3367	39000.0	3
U-251 CHEMBL615022	IC50	4.4	4.4	40000.0	1
A549 CHEMBL392	IC50	4.2	4.17	62900.0	2
MDA-MB-231 CHEMBL400	IC50	4.19	4.19	64000.0	1
Unchecked CHEMBL612545	EC50	4.16	4.16	69700.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	345.0	ng.hr.mL-1	Mus musculus
AUC	524.0	ng.hr.mL-1	Mus musculus
CL	96.8	mL.min-1.kg-1	Mus musculus
F	14.1	%	Mus musculus
F	30.0	%	Homo sapiens
T1/2	0.8333	hr	Mus musculus
T1/2	4.5	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Cytochrome P450 2C19	IC50	=	400.3	nM	6.4	DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	-
Tubulin beta	Kd	=	579.0	nM	6.24	Binding affinity to CM5 chip immobilized beta tubulin (unknown origin) assessed ...	32784088
Tubulin	Kd	=	1860.0	nM	5.73	Binding affinity to tubulin (unknown origin)	25811651
Solute carrier family 22 member 2	IC50	=	2600.0	nM	5.58	Inhibition of human OCT2-mediated ASP+ uptake expressed in HEK293 cells after 3 ...	23241029
Cytochrome P450 2C9	IC50	=	8177.3	nM	5.09	DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	-
CCRF-CEM	IC50	=	14500.0	nM	4.84	Cytotoxicity against human CEM cells	25811651
NCI/ADR-RES	IC50	=	17400.0	nM	4.76	Antiproliferative activity against human NCI/ADR-RES cells after 6 days by MTT a...	30156410
HeLa	EC50	=	18400.0	nM	4.74	Antimitotic activity against human HeLa cells	25811651
MCF7	IC50	=	18800.0	nM	4.73	Antiproliferative activity against human MCF7 cells after 6 days by MTT assay	30156410
NON-PROTEIN TARGET	IC50	=	20000.0	nM	4.7	Antiproliferative activity against human A172 cells assessed as decrease in colo...	25811651
HeLa	IC50	=	24000.0	nM	4.62	Antiproliferative activity against human HeLa cells after 72 hrs by MTS assay	25453814
HeLa	IC50	=	24000.0	nM	4.62	Cytotoxicity against human HeLa cells	25811651
A549	EC50	=	25000.0	nM	4.6	Effect on cell growth in A549 cells by MTS assay	16279766
HeLa	IC50	=	25000.0	nM	4.6	Cytotoxicity against human HeLa cells	30156410
HeLa	IC50	=	25000.0	nM	4.6	Antiproliferative activity against human HeLa cells assessed as inhibition of ce...	38352836
Multidrug and toxin extrusion protein 1	IC50	=	34500.0	nM	4.46	Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells after 1...	23241029
NON-PROTEIN TARGET	IC50	=	34700.0	nM	4.46	Cytotoxicity against human H460 cells after 72 hrs	25811651
Unchecked	IC50	=	39000.0	nM	4.41	Cytotoxicity against human Renal 1983 cells	30156410
Unchecked	IC50	=	39000.0	nM	4.41	Antiproliferative activity against Renal 1983 cells (unknown origin) assessed as...	38352836
U-251	IC50	=	40000.0	nM	4.4	Antiproliferative activity against human U251 cells assessed as decrease in colo...	25811651

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	168
-	10.5281/zenodo.13943903	ADMET	89
38352836	10.1021/acsmedchemlett.3c00462	MOLM-13	9
25811651	10.1021/jm501180v	Tubulin	8
22320354	10.1021/jm200848t	NON-PROTEIN TARGET	8
25811651	10.1021/jm501180v	HeLa	8
25811651	10.1021/jm501180v	U-251	7
16279766	10.1021/jm050674q	Mus musculus	6
25811651	10.1021/jm501180v	NON-PROTEIN TARGET	6
30156410	10.1021/acs.jmedchem.8b00986	Unchecked	6
22320354	10.1021/jm200848t	SNU-398	5
30156410	10.1021/acs.jmedchem.8b00986	MCF7	4
30156410	10.1021/acs.jmedchem.8b00986	PANC-1	4
22320354	10.1021/jm200848t	Molecular identity unknown	3
15828811	10.1021/jm0494220	HEK293	3
25050880	10.1016/j.ejmech.2014.07.050	Tubulin	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	3
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	3
37468498	10.1038/s41467-023-40064-9	Histamine H1 receptor	3

Data from ChEMBL 36 via Core Engine