Compound Detail

CHEMBL31410

CORYNANTHEINE

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COC(=O)[C@H]1[C@H]2C[C@H]3c4[nH]c5ccccc5c4CCN3C[C@@H]2CC[C@@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL31410
Name	CORYNANTHEINE
Phase	Preclinical
Structure Type	MOL
InChI Key	BLGXFZZNTVWLAY-DKJBZYCGSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

354.4

MW (Da)

2.65

ALogP

HBA

HBD

65.6

PSA (Å²)

0.77

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	C21H26N2O3
MW	354.45
Aromatic Rings	2
Heavy Atoms	26
NP-Likeness	1.17

Activity Summary

Kd 11 meas. best 6.6

Ki 10 meas. best 7.54

IC50 8 meas. best 6.66

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Alpha-1A adrenergic receptor CHEMBL229	Ki	7.54	7.195	29.0	2
Cytochrome P450 2D6 CHEMBL289	Ki	7.1	7.1	80.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.79	6.79	161.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	6.66	6.66	220.0	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	6.6	6.6	253.0	1
Alpha-1A adrenergic receptor CHEMBL229	Kd	6.6	6.6	251.2	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.34	6.34	455.0	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	6.29	6.29	517.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	6.25	6.25	562.3	1
Alpha-2A adrenergic receptor CHEMBL1867	Ki	5.91	5.91	1218.0	1
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	Ki	5.9	5.9	1250.0	1
Adrenergic receptor alpha-2 CHEMBL2095158	Kd	5.25	4.76	5600.0	3
Adrenergic receptor alpha-2 CHEMBL2093864	Kd	5.03	5.03	9332.5	1
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	4.8	4.8	15800.0	1
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	4.76	4.76	17500.0	1
Murine T-cell line CHEMBL614766	IC50	4.56	4.56	27600.0	1
B-cell line CHEMBL614724	IC50	4.39	4.39	40500.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Alpha-1A adrenergic receptor	Ki	=	29.0	nM	7.54	Binding constant measured against Alpha-1A adrenergic receptor in human prostate...	15664832
Cytochrome P450 2D6	Ki	=	80.0	nM	7.1	Inhibitory effect on Bufuralol 1'-hydroxylation by human liver microsomes (Ki = ...	8487254
Alpha-1A adrenergic receptor	Ki	=	142.0	nM	6.85	Inhibition of [3H]prazosin binding to human Alpha-1A adrenergic receptor express...	7562902
Alpha-2C adrenergic receptor	Ki	=	161.0	nM	6.79	Inhibition of [3H]rauwolscine to CHO cells expressing the human Alpha-2C adrener...	7562902
Adrenergic receptor alpha-1	IC50	=	220.0	nM	6.66	Inhibition of specific [3H]prazosin binding (0.2 nM) to rat brain membranes alph...	6142954
Alpha-1A adrenergic receptor	Kd	=	251.19	nM	6.6	Inhibition of specific [3H]prazosin binding (0.2 nM) to rat brain membranes alph...	6142954
Alpha-1D adrenergic receptor	Ki	=	253.0	nM	6.6	Inhibition of [3H]prazosin binding to human Alpha-1D adrenergic receptor express...	7562902
Alpha-2B adrenergic receptor	Ki	=	455.0	nM	6.34	Inhibition of [3H]rauwolscine binding to CHO cells expressing the human Alpha-2B...	7562902
Alpha-1B adrenergic receptor	Ki	=	517.0	nM	6.29	Inhibition of [3H]prazosin binding to human Alpha-1B adrenergic receptor express...	7562902
Adrenergic receptor alpha-1	Kd	=	562.34	nM	6.25	Antagonist activity against phenylephrine-induced alpha1- adrenoceptor mediated ...	6142954
Alpha-2A adrenergic receptor	Ki	=	1218.0	nM	5.91	Inhibition of [3H]rauwolscine binding to CHO cells expressing the human Alpha-2A...	7562902
Voltage-dependent L-type calcium channel subunit alpha-1C	Ki	=	1250.0	nM	5.9	Inhibition of [3H]nitrendipine binding to membrane homogenates of rat cardiac mu...	7562902
Adrenergic receptor alpha-2	Kd	=	5600.0	nM	5.25	Dissociation constant in high affinity sites where the binding is in 50 mM phosp...	-
Adrenergic receptor alpha-2	Kd	=	9332.54	nM	5.03	Antagonist activity against B-HT 933-induced alpha-2-adrenoceptor-mediated vasoc...	6142954
Adrenergic receptor alpha-2	Ki	=	15800.0	nM	4.8	The ability to displace [3H]clonidine from the Alpha-2 adrenergic receptor was d...	6296387
Adrenergic receptor alpha-2	IC50	=	17500.0	nM	4.76	Inhibition of specific [3H]clonidine binding (0.4 nM) to rat brain membranes Alp...	6142954
Adrenergic receptor alpha-2	Kd	=	25000.0	nM	4.6	Dissociation constant in high affinity sites where the binding is in 50 mM phosp...	-
Murine T-cell line	IC50	=	27600.0	nM	4.56	Immunosuppressive activity in C57BL/6 mouse T cells assessed as inhibition of Co...	30059216
Adrenergic receptor alpha-2	Kd	=	37000.0	nM	4.43	Dissociation constant in high affinity sites where the binding is in acetonitril...	-
B-cell line	IC50	=	40500.0	nM	4.39	Immunosuppressive activity in C57BL/6 mouse B cells assessed as inhibition of LP...	30059216

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1016/0960-894X(96)00406-4	Adrenergic receptor alpha-2	12
6142954	10.1021/jm00370a011	Adrenergic receptor alpha-2	3
16033273	10.1021/jm0408969	Unchecked	3
37938154	10.1021/acs.jnatprod.3c00661	20S proteasome	2
6142954	10.1021/jm00370a011	Adrenergic receptor alpha-1	2
6142954	10.1021/jm00370a011	Adrenergic receptor alpha	2
2579237	10.1021/jm00381a019	Sodium channel alpha subunits; brain (Types I, II, III)	1
8487254	10.1021/jm00061a004	Cytochrome P450 2D6	1
7562902	10.1021/jm00019a001	Alpha-1A adrenergic receptor	1
7562902	10.1021/jm00019a001	Alpha-1B adrenergic receptor	1
7562902	10.1021/jm00019a001	Alpha-1D adrenergic receptor	1
7562902	10.1021/jm00019a001	Alpha-2A adrenergic receptor	1
7562902	10.1021/jm00019a001	Alpha-2B adrenergic receptor	1
7562902	10.1021/jm00019a001	Alpha-2C adrenergic receptor	1
7562902	10.1021/jm00019a001	Voltage-dependent L-type calcium channel subunit alpha-1C	1
6296387	10.1021/jm00354a001	Adrenergic receptor alpha-2	1
6142954	10.1021/jm00370a011	Unchecked	1
15664832	10.1016/j.bmcl.2004.11.032	Alpha-1A adrenergic receptor	1
1710653	10.1021/np50073a012	Human immunodeficiency virus type 1 reverse transcriptase	1
23062825	10.1016/j.bmc.2012.09.040	Acetylcholinesterase	1

Data from ChEMBL 36 via Core Engine