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Compound Detail

CHEMBL16958

STAUROSPORINONE
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O=C1NCc2c1c1c3ccccc3[nH]c1c1[nH]c3ccccc3c21

Basic Information

ChEMBL ID CHEMBL16958
Name STAUROSPORINONE
Phase Preclinical
Structure Type MOL
InChI Key MEXUTNIFSHFQRG-UHFFFAOYSA-N
23
Targets
33
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

311.3
MW (Da)
4.20
ALogP
1
HBA
3
HBD
60.7
PSA (Ų)
0.39
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H13N3O
MW 311.34
Aromatic Rings 5
Heavy Atoms 24
NP-Likeness 0.60

Activity Summary

IC50 33 meas. best 7.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mitogen-activated protein kinase kinase kinase 11
CHEMBL2708
IC50 7.31 7.31 49.0 1
Tyrosine-protein kinase JAK3
CHEMBL2148
IC50 7.21 7.21 61.0 1
Mitogen-activated protein kinase kinase kinase 9
CHEMBL2872
IC50 6.86 6.86 138.0 1
CaM kinase II
CHEMBL2097164
IC50 6.74 6.74 184.0 1
Protein kinase C (PKC)
CHEMBL2093867
IC50 6.67 5.875 214.0 4
cGMP-dependent protein kinase 1
CHEMBL3183
IC50 6.19 6.19 650.0 1
Protein kinase C (PKC)
CHEMBL2094266
IC50 6.17 6.17 680.0 1
Cyclin-dependent kinase 4/cyclin D1
CHEMBL1907601
IC50 6.08 6.08 830.0 2
HCT-116
CHEMBL394
IC50 5.76 5.76 1720.0 2
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.76 5.76 1720.0 1
Zinc finger protein GLI1
CHEMBL5461
IC50 5.75 5.75 1800.0 1
Protein kinase C alpha type
CHEMBL299
IC50 5.61 5.61 2450.0 1
Zinc finger protein GLI2
CHEMBL5119
IC50 5.57 5.57 2700.0 1
Myosin light chain kinase, smooth muscle
CHEMBL3062
IC50 5.55 5.55 2800.0 1
NCI-H460
CHEMBL396
IC50 5.5 5.5 3200.0 2
P388
CHEMBL389
IC50 5.4 5.4 4000.0 1
B16
CHEMBL381
IC50 5.32 5.32 4800.0 1
K562
CHEMBL385
IC50 5.11 5.11 7800.0 1
Unchecked
CHEMBL612545
IC50 5.1 4.845 8000.0 4
Malate dehydrogenase
CHEMBL4255
IC50 5.1 5.1 8000.0 1
Beta-lactamase
CHEMBL2026
IC50 5.1 5.1 8000.0 1
Chymotrypsinogen B
CHEMBL4796
IC50 5.0 5.0 10000.0 1
cAMP-dependent protein kinase (PKA)
CHEMBL2094138
IC50 4.59 4.59 25700.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mitogen-activated protein kinase kinase kinase 11 IC50 = 49.0 nM 7.31 Inhibition of GST-MLK3 expressed in baculovirus 17266195
Tyrosine-protein kinase JAK3 IC50 = 61.0 nM 7.21 Inhibition of JAK3 expressed in insect Sf21 cells assessed as inhibition of biot... 19427203
Mitogen-activated protein kinase kinase kinase 9 IC50 = 138.0 nM 6.86 Inhibition of GST-MLK1 expressed in baculovirus 17266195
CaM kinase II IC50 = 184.0 nM 6.74 Inhibition of Calcium/calmodulin-dependent protein kinase type II 14552791
Protein kinase C (PKC) IC50 = 214.0 nM 6.67 Inhibition of PKC (unknown origin) incubated for 30 mins in presence of ATP by P... 1874734
cGMP-dependent protein kinase 1 IC50 = 650.0 nM 6.19 In vitro for inhibitory activity against cGMP-dependent protein kinase from bovi... -
Protein kinase C (PKC) IC50 = 680.0 nM 6.17 In vitro for inhibitory activity against protein kinase C from rat brain -
Cyclin-dependent kinase 4/cyclin D1 IC50 = 830.0 nM 6.08 Inhibitory activity against Cyclin D1-cyclin-dependent kinase 4 by measuring pho... 14552792
Cyclin-dependent kinase 4/cyclin D1 IC50 = 830.0 nM 6.08 Inhibitory activity against Cyclin D1-cyclin-dependent kinase 4 by measuring the... 14552791
HCT-116 IC50 = 1720.0 nM 5.76 In vitro antiproliferative activity against HCT116 ( human colon) cell line. 14552792
HCT-116 IC50 = 1720.0 nM 5.76 Inhibition of human HCT(colon) carcinoma cell proliferation 14552791
NON-PROTEIN TARGET IC50 = 1720.0 nM 5.76 Cytotoxicity against human HCT116 cells 27255178
Zinc finger protein GLI1 IC50 = 1800.0 nM 5.75 Inhibition of Gli1-mediated transcription expressed in human PANC1 cells 19309080
Protein kinase C (PKC) IC50 = 2450.0 nM 5.61 Inhibition of PKC (unknown origin) 28991459
Protein kinase C alpha type IC50 = 2450.0 nM 5.61 Inhibition of Protein Kinase C(PKC) 8893841
Protein kinase C (PKC) IC50 = 2450.0 nM 5.61 Inhibition of Protein kinase C 12672248
Protein kinase C (PKC) IC50 = 2450.0 nM 5.61 Inhibition of protein kinase C -
Zinc finger protein GLI2 IC50 = 2700.0 nM 5.57 Inhibition of Gli2-mediated transcription expressed in human PANC1 cells 19309080
Myosin light chain kinase, smooth muscle IC50 = 2800.0 nM 5.55 In vitro for inhibitory activity against myosin light-chain kinase from chicken ... -
NCI-H460 IC50 = 3200.0 nM 5.5 In vitro antiproliferative activity against NCI-460 (human lung) cell line. 14552792

Literature References

PubMed DOI Target Context # Activities
8893841 10.1021/jm9603779 Mus musculus 12
10998351 10.1042/0264-6021:3510095 Unchecked 5
13678405 10.1021/jm030266r Beta-lactamase 3
12672248 10.1021/jm020427b Beta-lactamase 2
33100009 10.1021/acs.jmedchem.0c01271 Protein kinase C theta type 2
19427203 10.1016/j.bmcl.2009.04.039 Jurkat 2
28991459 10.1021/acs.jmedchem.7b01231 Unchecked 2
14552791 10.1016/s0960-894x(03)00791-1 Cyclin-dependent kinase 4/cyclin D1 1
14552791 10.1016/s0960-894x(03)00791-1 Protein kinase C (PKC) 1
14552791 10.1016/s0960-894x(03)00791-1 cAMP-dependent protein kinase (PKA) 1
1874734 10.1016/s0021-9258(18)98476-0 Protein kinase C (PKC) 1
14552791 10.1016/s0960-894x(03)00791-1 Cyclin-dependent kinase 1/cyclin B 1
14552791 10.1016/s0960-894x(03)00791-1 NCI-H460 1
14552791 10.1016/s0960-894x(03)00791-1 HCT-116 1
14552792 10.1016/s0960-894x(03)00792-3 NCI-H460 1
14552792 10.1016/s0960-894x(03)00792-3 HCT-116 1
14552792 10.1016/s0960-894x(03)00792-3 Cyclin-dependent kinase 4/cyclin D1 1
- 10.1016/S0960-894X(01)80995-1 Splenocyte 1
- 10.1016/S0960-894X(01)80995-1 Myosin light chain kinase, smooth muscle 1
- 10.1016/S0960-894X(01)80995-1 cGMP-dependent protein kinase 1 1

Data from ChEMBL 36 via Core Engine