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Compound Detail

CHEMBL477989

SB590885
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CN(C)CCOc1ccc(-c2nc(-c3ccncc3)c(-c3ccc4c(c3)CC/C4=N\O)[nH]2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL477989
Name SB590885
Phase Preclinical
Structure Type MOL
InChI Key MLSAQOINCGAULQ-QFMPWRQOSA-N
214
Targets
631
Activities
4
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

453.6
MW (Da)
4.87
ALogP
6
HBA
2
HBD
86.6
PSA (Ų)
0.31
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C27H27N5O2
MW 453.55
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -0.74

Activity Summary

IC50 585 meas. best 9.8
EC50 31 meas. best 7.55
Ki 12 meas. best 9.8
Kd 3 meas. best 9.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase B-raf
CHEMBL5145
 IC50 9.8 6.3714 0.2 22
Serine/threonine-protein kinase B-raf
CHEMBL5145
 Kd 9.8 9.6133 0.2 3
Serine/threonine-protein kinase B-raf
CHEMBL5145
 Ki 9.8 9.76 0.2 7
Unchecked
CHEMBL612545
 Ki 9.8 9.8 0.2 1
RAF proto-oncogene serine/threonine-protein kinase
CHEMBL1906
 Ki 8.76 8.76 1.7 4
DU-4475
CHEMBL2366246
 IC50 7.63 7.63 23.5 1
RAF proto-oncogene serine/threonine-protein kinase
CHEMBL1906
 IC50 7.55 6.1732 28.0 19
Serine/threonine-protein kinase B-raf
CHEMBL5145
 EC50 7.55 6.5484 28.0 19
MEL-HO
CHEMBL1075500
 IC50 7.16 7.16 69.3 1
M14
CHEMBL614317
 IC50 7.09 7.09 80.8 1
C32
CHEMBL1075401
 IC50 7.0 7.0 99.6 1
COLO 205
CHEMBL614561
 EC50 7.0 7.0 100.0 1
SK-MEL-28
CHEMBL614919
 EC50 6.92 6.92 120.0 1
Malme-3M
CHEMBL614021
 EC50 6.82 6.82 150.0 1
EOL1
CHEMBL614489
 IC50 6.74 6.74 180.2 1
A-375
CHEMBL613859
 IC50 6.55 6.47 281.5 3
H-EMC-SS
CHEMBL1075451
 IC50 6.45 6.45 351.3 1
Unchecked
CHEMBL612545
 EC50 6.43 6.43 370.0 1
COLO-679
CHEMBL1075426
 IC50 6.41 6.41 386.4 1
H9
CHEMBL614806
 IC50 6.4 6.4 401.0 1
HT-144
CHEMBL2366291
 IC50 6.36 6.36 434.8 1
A101D
CHEMBL2366306
 IC50 6.3 6.3 500.0 1
RAF proto-oncogene serine/threonine-protein kinase
CHEMBL1906
 EC50 6.26 6.26 550.0 1
SK-MEL-2
CHEMBL614917
 EC50 6.26 6.11 550.0 2
RVH-421
CHEMBL1075567
 IC50 6.21 6.21 621.3 1
SK-MEL-2
CHEMBL614917
 IC50 6.13 6.13 737.5 1
BV-173
CHEMBL2366145
 IC50 6.11 6.11 770.5 1
SH-4
CHEMBL2366309
 IC50 6.09 6.09 811.9 1
SK-MEL3
CHEMBL614920
 IC50 6.09 6.09 817.7 1
WM-115
CHEMBL1075611
 IC50 6.07 6.07 850.4 1
HT-29
CHEMBL384
 EC50 6.06 6.06 870.0 1
COLO-829
CHEMBL2366275
 IC50 6.01 6.01 966.9 1
HCC2218
CHEMBL2366221
 IC50 5.97 5.97 1059.1 1
HCT-116
CHEMBL394
 EC50 5.96 5.65 1100.0 2
UACC-257
CHEMBL612796
 IC50 5.95 5.95 1131.3 1
HOP-92
CHEMBL613889
 IC50 5.95 5.95 1111.6 1
ACN
CHEMBL2366195
 IC50 5.94 5.94 1148.8 1
SK-MEL-30
CHEMBL1075577
 IC50 5.81 5.81 1551.4 1
SNU-5
CHEMBL614934
 IC50 5.8 5.8 1579.8 1
BHT-101
CHEMBL1075398
 IC50 5.79 5.79 1628.1 1
NKM-1
CHEMBL2366133
 IC50 5.78 5.78 1668.7 1
CP50-MEL-B
CHEMBL2366076
 IC50 5.76 5.76 1727.7 1
TYK-nu
CHEMBL1075601
 IC50 5.74 5.74 1801.4 1
PSN1
CHEMBL614241
 IC50 5.73 5.73 1873.4 1
C2BBe1
CHEMBL2366283
 IC50 5.71 5.71 1958.0 1
SNU1
CHEMBL614931
 IC50 5.54 5.54 2904.1 1
HAL-01
CHEMBL2366142
 IC50 5.53 5.53 2925.8 1
LOX IMVI
CHEMBL614096
 IC50 5.5 5.5 3187.9 1
P12-Ichikawa
CHEMBL614660
 IC50 5.46 5.46 3439.9 1
EW-3
CHEMBL2366307
 IC50 5.45 5.45 3557.8 1

Pharmacokinetic Data

Parameter Value Units Species
CL 45.0 mL.min-1.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine/threonine-protein kinase B-raf Ki = 0.16 nM 9.8 Inhibition of BRAF 22583669
Serine/threonine-protein kinase B-raf IC50 = 0.16 nM 9.8 Inhibition of full length human 6His-tagged BRAF V600E mutant expressed in bacul... 29461827
Serine/threonine-protein kinase B-raf Kd = 0.16 nM 9.8 Binding affinity to human N-His6-tagged B-Raf expressed in Sf9 cells 22024030
Serine/threonine-protein kinase B-raf Ki = 0.16 nM 9.8 Inhibition of human cloned wild type BRAF by ELISA-based MEK phosphorylation ass... 18783202
Serine/threonine-protein kinase B-raf Ki = 0.16 nM 9.8 Inhibition of N-terminus His-6 tagged human B-Raf expressed in baculovirus infec... 22222036
Unchecked Ki = 0.16 nM 9.8 Inhibition of full length GST-tagged mouse B-Raf V600E mutant-mediated MEK1 phos... 22985962
Serine/threonine-protein kinase B-raf Ki = 0.16 nM 9.8 Inhibition of B-Raf V600E mutant 22808911
Serine/threonine-protein kinase B-raf Ki = 0.16 nM 9.8 Inhibition of B-Raf (unknown origin) assessed as apparent inhibition constant 17145850
Serine/threonine-protein kinase B-raf Ki = 0.16 nM 9.8 Affinity Biochemical interaction: (Enzymatic assay) EUB0000655a BRAF -
Serine/threonine-protein kinase B-raf Kd = 0.3 nM 9.52 Binding affinity to B-Raf by fluorescene ligand binding assay 18621524
Serine/threonine-protein kinase B-raf Kd = 0.3 nM 9.52 Binding affinity at bRaf kinase in fluorescent ligand displacement assay 16260133
Serine/threonine-protein kinase B-raf Ki = 0.3 nM 9.52 Inhibition of B-Raf 22808911
RAF proto-oncogene serine/threonine-protein kinase Ki = 1.72 nM 8.76 Affinity Biochemical interaction: (Enzymatic assay) EUB0000655a RAF1 -
RAF proto-oncogene serine/threonine-protein kinase Ki = 1.72 nM 8.76 Inhibition of c-Raf (unknown origin) assessed as apparent inhibition constant 17145850
RAF proto-oncogene serine/threonine-protein kinase Ki = 1.72 nM 8.76 Inhibition of C-RAF 18783202
RAF proto-oncogene serine/threonine-protein kinase Ki = 1.72 nM 8.76 Inhibition of C-Raf 22808911
DU-4475 IC50 = 23.54 nM 7.63 SANGER: Inhibition of human DU-4475 cell growth in a cell viability assay. -
Serine/threonine-protein kinase B-raf IC50 = 28.0 nM 7.55 Affinity Phenotypic Cellular interaction: (Western blot assay (phosphorylation o... -
Serine/threonine-protein kinase B-raf EC50 = 28.0 nM 7.55 Inhibition of B-Raf V600E mutant-mediated Erk phosphorylation in human Colo205 c... 22222036
RAF proto-oncogene serine/threonine-protein kinase IC50 = 28.0 nM 7.55 Affinity Phenotypic Cellular interaction: (Western blot assay (phosphorylation o... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 261
- 10.6019/CHEMBL4689842 U2OS 261
- 10.6019/CHEMBL4689842 Fibroblast 257
17145850 10.1158/0008-5472.can-06-2554 Unchecked 50
- 10.6019/CHEMBL5444388 Serine/threonine-protein kinase B-raf 23
- 10.6019/CHEMBL5444388 RAF proto-oncogene serine/threonine-protein kinase 23
17145850 10.1158/0008-5472.can-06-2554 Serine/threonine-protein kinase B-raf 21
- 10.6019/CHEMBL5465560 Tyrosine-protein kinase ABL1 16
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5465560 Epidermal growth factor receptor 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5465560 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 11
22222036 10.1016/j.bmcl.2011.11.060 Serine/threonine-protein kinase B-raf 9
- 10.6019/CHEMBL5465560 Mast/stem cell growth factor receptor Kit 9
- 10.6019/CHEMBL5465560 Receptor-type tyrosine-protein kinase FLT3 8
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
18621524 10.1016/j.bmcl.2008.06.070 Unchecked 5
- 10.6019/CHEMBL5465560 Proto-oncogene tyrosine-protein kinase receptor Ret 4
- 10.6019/CHEMBL5465560 Hepatocyte growth factor receptor 4
- 10.6019/CHEMBL5465560 Serine/threonine-protein kinase B-raf 3

Data from ChEMBL 36 via Core Engine