Compound Detail

CHEMBL574737

UCN-01

🧪 Phase II

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🧪 Phase II

CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)N[C@H]4O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL574737
Name	UCN-01
Phase	Phase II
Structure Type	MOL
InChI Key	PBCZSGKMGDDXIJ-KRUBCLEUSA-N

Known Names

7-hydroxystaurosporine KRX-0601 KW-2401 NSC-638850 Ucn 01 Ucn-01 UCN-02

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

482.5

MW (Da)

3.84

ALogP

HBA

HBD

89.7

PSA (Å²)

0.36

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C28H26N4O4
MW	482.54
Aromatic Rings	5
Heavy Atoms	36
NP-Likeness	1.42

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Cyclin-dependent kinase 2 inhibitor	INHIBITOR	Cyclin-dependent kinase 2	✓	✓
Cyclin-dependent kinase 4 inhibitor	INHIBITOR	Cyclin-dependent kinase 4	✓	✓
Cyclin-dependent kinase 6 inhibitor	INHIBITOR	Cyclin-dependent kinase 6	✓	✓
Serine/threonine-protein kinase Chk1 inhibitor	INHIBITOR	Serine/threonine-protein kinase Chk1	✓	✓
3-phosphoinositide dependent protein kinase-1 inhibitor	INHIBITOR	3-phosphoinositide-dependent protein kinase 1	✓	✓
Protein kinase C (PKC) inhibitor	INHIBITOR	Protein kinase C (PKC)	✓	✓

Indications

Fallopian Tube Neoplasms Kidney Neoplasms Lymphoma Melanoma Ovarian Neoplasms Pancreatic Neoplasms Peritoneal Neoplasms Small Cell Lung Carcinoma Anus Neoplasms Appendiceal Neoplasms Breast Neoplasms Carcinoid Tumor Carcinoma, Basal Cell Carcinoma, Non-Small-Cell Lung Carcinoma, Ovarian Epithelial Carcinoma, Verrucous Endometrial Neoplasms Esophageal Neoplasms Esthesioneuroblastoma, Olfactory Gallbladder Neoplasms

Activity Summary

Kd 63 meas. best 8.52

IC50 8 meas. best 8.39

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Serine/threonine-protein kinase 10 CHEMBL3981	Kd	8.52	8.52	3.0	1
Serine/threonine-protein kinase PAK 6 CHEMBL4311	Kd	8.4	8.4	4.0	1
Protein kinase C (PKC) CHEMBL2093867	IC50	8.39	7.8	4.1	2
Serine/threonine-protein kinase Chk1 CHEMBL4630	IC50	8.25	8.125	5.6	2
MAP/microtubule affinity-regulating kinase 4 CHEMBL5754	Kd	8.1	8.1	8.0	1
Unchecked CHEMBL612545	Kd	8.1	8.1	8.0	1
Serine/threonine-protein kinase N1 CHEMBL3384	Kd	8.1	8.1	8.0	1
Serine/threonine-protein kinase Chk2 CHEMBL2527	IC50	8.0	8.0	10.0	1
Serine/threonine-protein kinase SIK2 CHEMBL5699	Kd	7.96	7.96	11.0	1
Serine/threonine-protein kinase MARK2 CHEMBL3831	Kd	7.89	7.89	13.0	1
MAP/microtubule affinity-regulating kinase 3 CHEMBL5600	Kd	7.8	7.8	16.0	1
Protein kinase C beta type CHEMBL3045	Kd	7.72	7.72	19.0	1
5'-AMP-activated protein kinase subunit gamma-2 CHEMBL2453	Kd	7.6	7.6	25.0	1
Serine/threonine-protein kinase PAK 4 CHEMBL4482	Kd	7.6	7.6	25.0	1
Cyclin-dependent kinase 2 CHEMBL301	IC50	7.52	7.52	30.0	1
Calcium/calmodulin-dependent protein kinase kinase 2 CHEMBL5284	Kd	7.52	7.52	30.0	1
Serine/threonine-protein kinase Chk1 CHEMBL4630	Kd	7.48	7.48	33.0	1
Protein kinase C alpha type CHEMBL299	Kd	7.46	7.46	35.0	1
Protein kinase C delta type CHEMBL2996	Kd	7.42	7.42	38.0	1
cAMP-dependent protein kinase (PKA) CHEMBL2094138	IC50	7.38	6.99	42.0	2
Serine/threonine-protein kinase 3 CHEMBL4708	Kd	7.35	7.35	45.0	1
Serine/threonine-protein kinase SIK3 CHEMBL6149	Kd	7.25	7.25	56.0	1
Receptor-type tyrosine-protein kinase FLT3 CHEMBL1974	Kd	7.17	7.17	67.0	1
STE20-like serine/threonine-protein kinase CHEMBL4202	Kd	7.05	7.05	89.0	1
Serine/threonine-protein kinase MRCK beta CHEMBL5052	Kd	6.96	6.96	110.0	1
Serine/threonine-protein kinase 4 CHEMBL4598	Kd	6.94	6.94	114.0	1
Serine/threonine-protein kinase N2 CHEMBL3032	Kd	6.85	6.85	142.0	1
Ribosomal protein S6 kinase alpha-6 CHEMBL4924	Kd	6.85	6.85	141.0	1
Activated CDC42 kinase 1 CHEMBL4599	Kd	6.79	6.79	162.0	1
Protein-tyrosine kinase 2-beta CHEMBL5469	Kd	6.72	6.72	191.0	1
Tyrosine-protein kinase SYK CHEMBL2599	Kd	6.66	6.66	217.0	1
Serine/threonine-protein kinase MRCK alpha CHEMBL4516	Kd	6.59	6.59	254.0	1
Serine/threonine-protein kinase MRCK gamma CHEMBL5615	Kd	6.57	6.57	269.0	1
Mitogen-activated protein kinase kinase kinase 11 CHEMBL2708	Kd	6.52	6.52	303.0	1
5'-AMP-activated protein kinase catalytic subunit alpha-1 CHEMBL4045	Kd	6.5	6.5	319.0	1
Tyrosine-protein kinase BTK CHEMBL5251	Kd	6.41	6.41	386.0	1
Serine/threonine-protein kinase TBK1 CHEMBL5408	Kd	6.41	6.41	393.0	1
Serine/threonine-protein kinase 38-like CHEMBL4851	Kd	6.38	6.38	414.0	1
Tyrosine-protein kinase Fer CHEMBL3982	Kd	6.37	6.37	430.0	1
Focal adhesion kinase 1 CHEMBL2695	Kd	6.36	6.36	436.0	1
Platelet-derived growth factor receptor beta CHEMBL1913	Kd	6.36	6.36	436.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	6.28	6.28	521.0	1
Calcium/calmodulin-dependent protein kinase type II subunit delta CHEMBL2801	Kd	6.28	6.28	520.0	1
Inhibitor of nuclear factor kappa-B kinase subunit epsilon CHEMBL3529	Kd	6.28	6.28	528.0	1
AP2-associated protein kinase 1 CHEMBL3830	Kd	6.21	6.21	623.0	1
Tyrosine-protein kinase HCK CHEMBL3234	Kd	6.21	6.21	621.0	1
Septin-9 CHEMBL4105891	Kd	6.2	6.2	635.0	1
Mitogen-activated protein kinase kinase kinase kinase 2 CHEMBL5330	Kd	6.2	6.2	631.0	1
Aurora kinase B CHEMBL2185	Kd	6.17	6.17	670.0	1
Mitogen-activated protein kinase kinase kinase kinase 3 CHEMBL5432	Kd	6.15	6.15	706.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Serine/threonine-protein kinase 10	Kd	=	3.0	nM	8.52	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Serine/threonine-protein kinase PAK 6	Kd	=	4.0	nM	8.4	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Protein kinase C (PKC)	IC50	=	4.1	nM	8.39	Inhibition of protein kinase C	-
Serine/threonine-protein kinase Chk1	IC50	=	5.6	nM	8.25	Inhibition of human recombinant Chk1	20943405
MAP/microtubule affinity-regulating kinase 4	Kd	=	8.0	nM	8.1	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Serine/threonine-protein kinase N1	Kd	=	8.0	nM	8.1	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Unchecked	Kd	=	8.0	nM	8.1	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Serine/threonine-protein kinase Chk2	IC50	=	10.0	nM	8.0	Inhibition of CHK2	20673630
Serine/threonine-protein kinase Chk1	IC50	=	10.0	nM	8.0	Inhibition of CHK1	20673630
Serine/threonine-protein kinase SIK2	Kd	=	11.0	nM	7.96	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Serine/threonine-protein kinase MARK2	Kd	=	13.0	nM	7.89	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
MAP/microtubule affinity-regulating kinase 3	Kd	=	16.0	nM	7.8	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Protein kinase C beta type	Kd	=	19.0	nM	7.72	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Serine/threonine-protein kinase PAK 4	Kd	=	25.0	nM	7.6	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
5'-AMP-activated protein kinase subunit gamma-2	Kd	=	25.0	nM	7.6	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Calcium/calmodulin-dependent protein kinase kinase 2	Kd	=	30.0	nM	7.52	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Cyclin-dependent kinase 2	IC50	=	30.0	nM	7.52	Inhibition of CDK2 (unknown origin)	-
Serine/threonine-protein kinase Chk1	Kd	=	33.0	nM	7.48	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Protein kinase C alpha type	Kd	=	35.0	nM	7.46	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878
Protein kinase C delta type	Kd	=	38.0	nM	7.42	Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ...	29191878

Literature References

PubMed	DOI	Target Context	# Activities
29191878	10.1126/science.aan4368	Unchecked	4
-	10.1016/S0960-894X(00)80167-5	cAMP-dependent protein kinase (PKA)	2
17850214	10.1042/bj20070797	Unchecked	2
-	10.1016/S0960-894X(00)80167-5	Protein kinase C (PKC)	2
17850214	10.1042/bj20070797	Serine/threonine-protein kinase pim-3	1
27414067	10.1021/acs.jmedchem.6b00618	ADMET	1
17850214	10.1042/bj20070797	Serine/threonine-protein kinase D1	1
17850214	10.1042/bj20070797	Protein kinase C zeta type	1
17850214	10.1042/bj20070797	Protein kinase C alpha type	1
17850214	10.1042/bj20070797	RAC-beta serine/threonine-protein kinase	1
17850214	10.1042/bj20070797	RAC-alpha serine/threonine-protein kinase	1
17850214	10.1042/bj20070797	cAMP-dependent protein kinase catalytic subunit alpha	1
17850214	10.1042/bj20070797	Mitogen-activated protein kinase 13	1
17850214	10.1042/bj20070797	Serine/threonine-protein kinase pim-2	1
17850214	10.1042/bj20070797	Serine/threonine-protein kinase pim-1	1
17850214	10.1042/bj20070797	Ribosomal protein S6 kinase alpha-1	1
17850214	10.1042/bj20070797	3-phosphoinositide-dependent protein kinase 1	1
17850214	10.1042/bj20070797	Serine/threonine-protein kinase PAK 6	1
17850214	10.1042/bj20070797	Serine/threonine-protein kinase PAK 5	1
17850214	10.1042/bj20070797	Serine/threonine-protein kinase PAK 4	1

Data from ChEMBL 36 via Core Engine