Compound 1604

Identifiers

Common name: I-BET151

Canonical SMILES:

COc1cc2c3n([C@H](C)c4ccccn4)c(=O)[nH]c3cnc2cc1-c1c(C)noc1C

IUPAC name:

7-(dimethyl-1,2-oxazol-4-yl)-8-methoxy-1-[(1R)-1-(pyridin-2-yl)ethyl]-3H-imidazo[4,5-c]quinolin-2-one

InChi:

InChI=1S/C23H21N5O3/c1-12-21(14(3)31-27-12)16-9-18-15(10-20(16)30-4)22-19(11-25-18)26-23(29)28(22)13(2)17-7-5-6-8-24-17/h5-11,13H,1-4H3,(H,26,29)/t13-/m1/s1

InChiKey:
```
VUVUVNZRUGEAHB-CYBMUJFWSA-N
```

External links

52912189

CHEMBL2017291

1GH

External search

Bibliography (1)

Publication	Name
Dawson MA, Prinjha RK, Dittmann A, Giotopoulos G, Bantscheff M, Chan WI, Robson SC, Chung CW, Hopf C, Savitski MM, Huthmacher C, Gudgin E, Lugo D, Beinke S, Chapman TD, Roberts EJ, Soden PE, Auger KR, Mirguet O, Doehner K, Delwel R, Burnett AK, Jeffrey P, Drewes G, Lee K, Huntly BJ, Kouzarides T. . Inhibition of BET recruitment to chromatin as an effective treatment for MLL-fusion leukaemia. Nature.	I-BET151

Publication

Name

Dawson MA, Prinjha RK, Dittmann A, Giotopoulos G, Bantscheff M, Chan WI, Robson SC, Chung CW, Hopf C, Savitski MM, Huthmacher C, Gudgin E, Lugo D, Beinke S, Chapman TD, Roberts EJ, Soden PE, Auger KR, Mirguet O, Doehner K, Delwel R, Burnett AK, Jeffrey P, Drewes G, Lee K, Huntly BJ, Kouzarides T. . Inhibition of BET recruitment to chromatin as an effective treatment for MLL-fusion leukaemia. Nature.

I-BET151

Pharmacological data

Biochemical tests	Cellular tests	PK tests	Cytotoxicity tests
5	12	0	0

Targets

PPI family	Best activity	Diseases	MMoA
Bromodomain / Histone	7.82	cancer	Inhibition

Physicochemical filters

Descriptor	Lipinski's RO5	Veber	Pfizer's 3/75
MW	≤ 500 g/mol	-	-
AlogP	≤ 5	-	≤ 3
HBA	≤ 10	-	-
HBD	≤ 5	-	-
(HBA + HBD)	-	≤ 12	-
TPSA	-	≤ 140 Å²	≥ 75 Å²
RB	-	≤ 10	-

	Descriptor	Lipinski's RO5	Veber	Pfizer's 3/75
Compliance
MW	415.16 g/mol
HBA	8
HBD	1
HBA + HBD	9
AlogP	2.69
TPSA	93.38
RB	3

Radar chart

Short name	Threshold
MW	≤ 500 g/mol
AlogP	≤ 5
HBD	≤ 5
HBA	≤ 10
TPSA	≤ 140 Å²
RB	≤ 10
ArRing	≤ 4
Fsp3	≥ 0.4
R/S	≥ 1

PCA : iPPI-DB chemical space

PCA : Correlation circle

Efficiencies: iPPI-DB biplot LE versus LLE

Summary

Bibliographic ressources	Biochemical tests	Cellular tests	PK tests	Cytotoxicity tests
1	5	12	0	0

Pharmacological data

Bibliography	Name	Target	Assay type	Assay name	Cell line	Activity type	Activity
21964340	I-BET151	BRD2 P25440	Biochemical assay	Fluorescence Polarization		pIC50 (half maximal inhibitory concentration, -log10)	6.30
21964340	I-BET151	BRD3 Q15059	Biochemical assay	Fluorescence Polarization		pIC50 (half maximal inhibitory concentration, -log10)	6.60
21964340	I-BET151	BRD4 O60885	Biochemical assay	Fluorescence Polarization		pIC50 (half maximal inhibitory concentration, -log10)	6.10
21964340	I-BET151	BRD3 Q15059	Biochemical assay	Surface Plasmon Resonance		pKd (dissociation constant, -log10)	7.70
21964340	I-BET151	BRD4 O60885	Biochemical assay	Surface Plasmon Resonance		pKd (dissociation constant, -log10)	7.00
21964340	I-BET151	BRD4 O60885	Cellular assay	LPS-stimulated IL6 production	PBMC	pIC50 (half maximal inhibitory concentration, -log10)	6.80
21964340	I-BET151	BRD4 O60885	Cellular assay	LPS-stimulated IL6 production	Human Whole Blood	pIC50 (half maximal inhibitory concentration, -log10)	5.90
21964340	I-BET151	BRD4 O60885	Cellular assay	LPS-stimulated IL6 production	Rat Whole Blood	pIC50 (half maximal inhibitory concentration, -log10)	5.90
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-fusion leukaemic proliferation	MV4-11	pIC50 (half maximal inhibitory concentration, -log10)	7.59
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-fusion leukaemic proliferation	RS4-11	pIC50 (half maximal inhibitory concentration, -log10)	6.72
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-fusion leukaemic proliferation	MOLM-13	pIC50 (half maximal inhibitory concentration, -log10)	6.92
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-fusion leukaemic proliferation	NOMO1	pIC50 (half maximal inhibitory concentration, -log10)	7.82
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-fusion leukaemic proliferation	HEL	pIC50 (half maximal inhibitory concentration, -log10)	6.00
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-fusion leukaemic proliferation	MEG01	pIC50 (half maximal inhibitory concentration, -log10)	4.60
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-fusion leukaemic proliferation	HL60	pIC50 (half maximal inhibitory concentration, -log10)	6.05
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-ENL-fusion leukaemic proliferation	MSCV transformed haematopoietic progenitors	pIC50 (half maximal inhibitory concentration, -log10)	6.38
21964340	I-BET151	BRD4 O60885	Cellular assay	MLL-AF9-fusion leukaemic proliferation	MSCV transformed haematopoietic progenitors	pIC50 (half maximal inhibitory concentration, -log10)	6.24

Ta	Name	Drugbank ID
0.4856	Alobresib	DB14970
0.4689	Rilematovir	DB15672
0.4605	Dactolisib	DB11651
0.4490	ATX-914	DB12673
0.4312	BMS-986142	DB15291
0.4231	MK-0249	DB11910
0.4197	Fulacimstat	DB15085
0.4148	LY-3023414	DB12167
0.4128	BIIB021	DB12359
0.4091	2-((9H-PURIN-6-YLTHIO)METHYL)-5-CHLORO-3-(2-METHOXYPHENYL)QUINAZOLIN-4(3H)-ONE	DB06831
0.4081	Gepotidacin	DB12134
0.4047	Dilmapimod	DB12140
0.4043	Merestinib	DB12381
0.4025	Dasabuvir	DB09183
0.4024	1-(2-Fluorobenzyl)-3-Butyl-8-(N-Acetyl-4-Aminobenzyl)-Xanthine	DB02008