4-[2-(Methoxymethyl)-1-[(R)-1-phenylethyl]-8-[(S)-pyrrolidin-3-ylmethoxy]-1H-imidazo[4,5-c]quinolin-7-yl]-3,5-dimethylisoxazole

ID: ALA4639128

Chembl Id: CHEMBL4639128

PubChem CID: 146018691

Max Phase: Preclinical

Molecular Formula: C30H33N5O3

Molecular Weight: 511.63

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COCc1nc2cnc3cc(-c4c(C)noc4C)c(OC[C@H]4CCNC4)cc3c2n1[C@H](C)c1ccccc1

Standard InChI:  InChI=1S/C30H33N5O3/c1-18-29(20(3)38-34-18)24-12-25-23(13-27(24)37-16-21-10-11-31-14-21)30-26(15-32-25)33-28(17-36-4)35(30)19(2)22-8-6-5-7-9-22/h5-9,12-13,15,19,21,31H,10-11,14,16-17H2,1-4H3/t19-,21+/m1/s1

Standard InChI Key:  ZORLJXWXFABTPZ-CTNGQTDRSA-N

Alternative Forms

1. Parent:

   

   ALA4639128

   GSK778

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: Yes

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 511.63

Molecular Weight (Monoisotopic): 511.2583

AlogP: 5.60

#Rotatable Bonds: 8

Polar Surface Area: 87.23

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 10.99

CX LogP: 3.62

CX LogD: 0.54

Aromatic Rings: 5

Heavy Atoms: 38

QED Weighted: 0.29

Np Likeness Score: -0.92

References

1. Wellaway CR, Bamborough P, Bernard SG, Chung CW, Craggs PD, Cutler L, Demont EH, Evans JP, Gordon L, Karamshi B, Lewis AJ, Lindon MJ, Mitchell DJ, Rioja I, Soden PE, Taylor S, Watson RJ, Willis R, Woolven JM, Wyspiańska BS, Kerr WJ, Prinjha RK..  (2020)  Structure-Based Design of a Bromodomain and Extraterminal Domain (BET) Inhibitor Selective for the N-Terminal Bromodomains That Retains an Anti-inflammatory and Antiproliferative Phenotype.,  63  (17): [PMID:32787145] [10.1021/acs.jmedchem.0c00566]

2. SGC Frankfurt.  (2021)  Data for DCP probe GSK778,  [10.6019/CHEMBL4630907]

3. Cui H, Carlson AS, Schleiff MA, Divakaran A, Johnson JA, Buchholz CR, Zahid H, Vail NR, Shi K, Aihara H, Harki DA, Miller GP, Topczewski JJ, Pomerantz WCK..  (2021)  4-Methyl-1,2,3-Triazoles as N-Acetyl-Lysine Mimics Afford Potent BET Bromodomain Inhibitors with Improved Selectivity.,  64  (14.0): [PMID:34236185] [10.1021/acs.jmedchem.1c00933]

4. Kong B, Zhu Z, Li H, Hong Q, Wang C, Ma Y, Zheng W, Jiang F, Zhang Z, Ran T, Bian Y, Yang N, Lu T, Zhu J, Tang W, Chen Y..  (2022)  Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy.,  227  [PMID:34731760] [10.1016/j.ejmech.2021.113953]

5. Tang P, Zhang J, Liu J, Chiang CM, Ouyang L..  (2021)  Targeting Bromodomain and Extraterminal Proteins for Drug Discovery: From Current Progress to Technological Development.,  64  (5.0): [PMID:33616410] [10.1021/acs.jmedchem.0c01487]

6. EUbOPEN.  (2023)  EUbOPEN Chemogenomics Library - IncuCyte,  [10.6019/CHEMBL5303304]

7. EUbOPEN.  (2023)  Tm Shift (DSF) assay results for EUbOPEN Chemogenomics Library,  [10.6019/CHEMBL5308504]

Source

Source(3):

• Scientific Literature
• Donated Chemical Probes - SGC Frankfurt
• EUbOPEN Chemogenomic Library