4-(5-bromothiophene-2-carbonyl)-5-(3,5-dimethylphenyl)-7-methyl-4,5-dihydro-1H-benzo[e][1,4]diazepin-2(3H)-one

ID: ALA5085334

PubChem CID: 166632839

Max Phase: Preclinical

Molecular Formula: C23H21BrN2O2S

Molecular Weight: 469.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C)cc(C2c3cc(C)ccc3NC(=O)CN2C(=O)c2ccc(Br)s2)c1

Standard InChI:  InChI=1S/C23H21BrN2O2S/c1-13-4-5-18-17(11-13)22(16-9-14(2)8-15(3)10-16)26(12-21(27)25-18)23(28)19-6-7-20(24)29-19/h4-11,22H,12H2,1-3H3,(H,25,27)

Standard InChI Key:  NIPTUMFVYBXSMZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   32.2289  -11.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2278  -12.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9425  -13.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9407  -11.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5129  -13.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0735  -13.1030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4054  -12.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0293  -11.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2873  -13.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6591  -12.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6561  -11.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2577  -11.4829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1137  -14.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3264  -14.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1511  -15.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7622  -15.7101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5512  -15.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7228  -14.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5250  -10.9941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6052  -13.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3249  -14.5097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4174  -13.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0098  -14.1571    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.7374  -13.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5922  -12.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7750  -12.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4798  -14.1280    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   32.3653  -15.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1639  -16.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 10  2  0
 11  4  2  0
  4  1  1  0
  2  5  1  0
  6  7  1  0
  7  8  1  0
  6  9  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  9 10  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  9 13  1  0
  8 19  2  0
  6 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  2  0
 24 27  1  0
 15 28  1  0
 17 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5085334

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 469.40

Molecular Weight (Monoisotopic): 468.0507

AlogP: 5.62

#Rotatable Bonds: 2

Polar Surface Area: 49.41

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.22

CX Basic pKa: ┄

CX LogP: 6.11

CX LogD: 6.11

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -1.20

References

1. Shen Y, Li F, Szewczyk MM, Halabelian L, Chau I, Eram MS, Dela Seña C, Park KS, Meng F, Chen H, Zeng H, Dong A, Wu H, Trush VV, McLeod D, Zepeda-Velázquez CA, Campbell RM, Mader MM, Watson BM, Schapira M, Arrowsmith CH, Al-Awar R, Barsyte-Lovejoy D, Kaniskan HÜ, Brown PJ, Vedadi M, Jin J..  (2021)  A First-in-Class, Highly Selective and Cell-Active Allosteric Inhibitor of Protein Arginine Methyltransferase 6.,  64  (7.0): [PMID:33591753] [10.1021/acs.jmedchem.0c02160]

Source

Source(1):

• Scientific Literature