Compound Detail

CHEMBL573214

NORBINALTORPHIMINE

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Oc1ccc2c3c1O[C@H]1c4[nH]c5c(c4C[C@@]4(O)[C@@H](C2)N(CC2CC2)CC[C@]314)C[C@@]1(O)[C@H]2Cc3ccc(O)c4c3[C@@]1(CCN2CC1CC1)[C@H]5O4

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL573214
Name	NORBINALTORPHIMINE
Phase	Preclinical
Structure Type	MOL
InChI Key	APSUXPSYBJVPPS-YAUKWVCOSA-N

Targets

150

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

661.8

MW (Da)

3.82

ALogP

HBA

HBD

121.7

PSA (Å²)

0.29

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C40H43N3O6
MW	661.80
Aromatic Rings	3
Heavy Atoms	49
NP-Likeness	0.84

Activity Summary

Ki 123 meas. best 10.57

IC50 22 meas. best 9.55

EC50 4 meas. best 8.22

Kd 1 meas. best 8.78

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Kappa-type opioid receptor CHEMBL237	Ki	10.57	9.5604	0.0	24
Kappa-type opioid receptor CHEMBL3952	Ki	10.42	9.262	0.0	15
Cavia porcellus CHEMBL369	Ki	10.42	8.868	0.0	5
Kappa-type opioid receptor CHEMBL3614	Ki	10.15	9.31	0.1	7
Mu-type opioid receptor CHEMBL270	Ki	9.66	7.8475	0.2	12
Kappa-type opioid receptor CHEMBL237	IC50	9.55	8.6225	0.3	8
Delta-type opioid receptor CHEMBL236	Ki	9.52	8.0235	0.3	23
Mu-type opioid receptor CHEMBL233	Ki	9.03	7.6787	0.9	15
Kappa-type opioid receptor CHEMBL4329	Kd	8.78	8.78	1.6	1
Kappa-type opioid receptor CHEMBL4329	IC50	8.54	8.54	2.9	1
Unchecked CHEMBL612545	IC50	8.34	8.335	4.6	2
Delta-type opioid receptor CHEMBL3222	Ki	8.28	7.8033	5.2	3
Delta-type opioid receptor CHEMBL269	Ki	8.24	7.2657	5.8	7
Kappa-type opioid receptor CHEMBL237	EC50	8.22	8.22	6.0	1
Kappa-type opioid receptor CHEMBL3952	IC50	8.22	7.48	6.0	2
Mu-type opioid receptor CHEMBL4354	IC50	8.08	7.915	8.3	2
Delta-type opioid receptor CHEMBL3222	IC50	7.98	7.98	10.4	1
Opioid receptors; mu/kappa/delta CHEMBL2095181	IC50	7.96	7.96	11.0	1
Mu-type opioid receptor CHEMBL4354	Ki	7.83	7.536	14.8	10
Delta-type opioid receptor CHEMBL236	IC50	7.66	7.6333	22.0	3
Unchecked CHEMBL612545	Ki	7.53	7.53	29.3	2
Mu-type opioid receptor CHEMBL233	EC50	6.92	6.92	120.0	1
c-Jun N-terminal kinase, JNK CHEMBL2096667	EC50	6.8	6.8	158.0	1
Mu-type opioid receptor CHEMBL233	IC50	6.67	6.67	212.0	2
Delta-type opioid receptor CHEMBL236	EC50	6.42	6.42	380.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Ke	0.572	nM	Cavia porcellus
Ke	0.55	nM	Cavia porcellus
Ke	14.0	nM	Cavia porcellus
Ke	10.6	nM	-
Ke	0.21	nM	Cavia porcellus
Ke	22.0	nM	Cavia porcellus
Ke	18.9	nM	-
Ke	4.42	nM	-
Ke	0.04	nM	-
Ke	0.56	nM	Cavia porcellus
Ke	13.7	nM	Cavia porcellus
Ke	10.6	nM	-
Ke	18.9	nM	-
Ke	4.42	nM	-
Ke	0.04	nM	-
Ke	0.55	nM	-
Ke	0.41	nM	Cavia porcellus
Ke	12.5	nM	Cavia porcellus
Ke	10.0	nM	Cavia porcellus
Ke	0.41	nM	Cavia porcellus
Ke	10.6	nM	-
Ke	12.5	nM	Cavia porcellus
Ke	19.0	nM	-
Ke	4.6	nM	-
Ke	0.04	nM	-
Ke	0.357	nM	Cavia porcellus
Ke	0.572	nM	Cavia porcellus
Ke	0.41	nM	Cavia porcellus
Ke	13.0	nM	Cavia porcellus
Ke	20.0	nM	Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Kappa-type opioid receptor	Ki	=	0.027	nM	10.57	Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cel...	19027293
Kappa-type opioid receptor	Ki	=	0.038	nM	10.42	Inhibition of [35S]GTP-gamma-S, binding from Opioid receptor kappa 1 in Guinea p...	9857089
Kappa-type opioid receptor	Ki	=	0.038	nM	10.42	Inhibition of stimulation of [35S]GTP-gamma-S, binding produced by the selective...	11495579
Cavia porcellus	Ki	=	0.038	nM	10.42	Functional antagonism was obtained by the ability of compound to inhibit stimula...	14761209
Kappa-type opioid receptor	Ki	=	0.039	nM	10.41	Compound was evaluated for its binding affinity by displacing [3H]U-69593 to hum...	11055333
Kappa-type opioid receptor	Ki	=	0.07	nM	10.15	Antagonist activity on agonist (U50,488) stimulated [35S]GTP-gamma-S, binding in...	11495579
Kappa-type opioid receptor	Ki	=	0.07	nM	10.15	Displacement of [3H]diprenorphine from opioid receptor kappa 1 expressed in HEK ...	11300867
Kappa-type opioid receptor	Ki	=	0.12	nM	9.92	Antagonist activity on agonist stimulated [35S]GTP-gamma-S, binding in guinea pi...	12565965
Kappa-type opioid receptor	Ki	=	0.12	nM	9.92	Effect on binding affinity of mutational exchange of Glu297 in the Opioid recept...	9836606
Kappa-type opioid receptor	Ki	=	0.1259	nM	9.9	Displacement of [3H]diprenorphine from human recombinant kappa opioid receptor e...	17490886
Cavia porcellus	Ki	=	0.13	nM	9.89	Functional antagonism was obtained by the ability of compound to inhibit stimula...	14761209
Kappa-type opioid receptor	Ki	=	0.13	nM	9.89	Binding affinity using [3H]diprenorphine as the radioligand against wild-type Op...	10780914
Kappa-type opioid receptor	Ki	=	0.15	nM	9.82	Antagonist activity at kappa opioid receptor (unknown origin)	25513968
Kappa-type opioid receptor	Ki	=	0.153	nM	9.81	Displacement of [3H]diprenorphine from human opioid kappa receptor expressed in ...	21958337
Kappa-type opioid receptor	Ki	=	0.19	nM	9.72	Displacement of [125I]-IBNalA from KOR-1 expressed in CHO cells	21621410
Kappa-type opioid receptor	Ki	=	0.2	nM	9.7	Inhibition of [3H]U-69593 binding to human kappa opioid receptor expressed in CH...	15456250
Kappa-type opioid receptor	Ki	=	0.2	nM	9.7	Displacement of [3H]U69593 from human recombinant kappa opioid receptor expresse...	24973818
Kappa-type opioid receptor	Ki	=	0.2	nM	9.7	Binding affinity against cloned human Opioid receptor kappa 1 transfected into c...	14640558
Kappa-type opioid receptor	Ki	=	0.2	nM	9.7	Compound was evaluated for its binding affinity to CHO cells expressing cloned h...	11055333
Kappa-type opioid receptor	Ki	=	0.2	nM	9.7	Binding affinity towards human cloned Opioid receptor kappa 1 using [3H]U-69593	12825951

Literature References

PubMed	DOI	Target Context	# Activities
9836606	10.1021/jm9805182	Kappa-type opioid receptor	8
1849995	10.1021/jm00108a008	Mu-type opioid receptor	6
14761209	10.1021/jm030467v	Cavia porcellus	6
25593096	10.1016/j.bmc.2014.12.033	Kappa-type opioid receptor	5
1849995	10.1021/jm00108a008	Kappa-type opioid receptor	5
20568781	10.1021/jm1004978	Kappa-type opioid receptor	4
12825951	10.1021/jm030094y	Kappa-type opioid receptor	4
12825951	10.1021/jm030094y	Opioid receptors; delta & kappa	4
14761209	10.1021/jm030467v	Opioid receptors; delta & kappa	4
14761209	10.1021/jm030467v	Opioid receptors; mu & kappa	4
11055333	10.1016/s0960-894x(00)00433-9	Opioid receptors; delta & kappa	4
12825951	10.1021/jm030094y	Mu-type opioid receptor	4
12825951	10.1021/jm030094y	Delta-type opioid receptor	4
20568781	10.1021/jm1004978	Delta-type opioid receptor	4
1849995	10.1021/jm00108a008	Delta-type opioid receptor	4
17702750	10.1074/jbc.m705540200	c-Jun N-terminal kinase, JNK	4
15163177	10.1021/jm0342358	Mus musculus	4
8182708	10.1021/jm00036a015	Unchecked	4
12747782	10.1021/jm020125+	Kappa-type opioid receptor	4
12825951	10.1021/jm030094y	Opioid receptors; mu & kappa	4

Data from ChEMBL 36 via Core Engine