methyl 3-(3-methyl-4-oxo-4,5,6,7-tetrahydro-2H-isoindol-1-yl)-4-phenoxybenzoate

ID: ALA4080666

PubChem CID: 71812065

Max Phase: Preclinical

Molecular Formula: C23H21NO4

Molecular Weight: 375.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(Oc2ccccc2)c(-c2[nH]c(C)c3c2CCCC3=O)c1

Standard InChI:  InChI=1S/C23H21NO4/c1-14-21-17(9-6-10-19(21)25)22(24-14)18-13-15(23(26)27-2)11-12-20(18)28-16-7-4-3-5-8-16/h3-5,7-8,11-13,24H,6,9-10H2,1-2H3

Standard InChI Key:  NPKQOBAGAPKRFP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   30.3720  -11.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3708  -12.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0859  -12.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8025  -12.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7997  -11.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0841  -11.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0822  -10.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6680   -9.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4128   -9.9575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1797   -8.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4927   -9.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7490   -9.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5516  -10.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1035   -9.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8430   -8.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0348   -8.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7772   -7.7701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5128  -11.2604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2290  -11.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2288  -12.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9442  -12.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6541  -12.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6484  -11.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9365  -11.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6559  -12.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9457  -12.5027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6552  -13.7423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9463  -11.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7 12  2  0
 11  8  2  0
  8  9  1  0
  9  7  1  0
  6  7  1  0
  8 10  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  2 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4080666

   methyl 3-(3-methyl-4-oxo-4,5,6,7-tetrahydro-2H-isoindol-1-yl)-4-phenoxybenzoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 375.42

Molecular Weight (Monoisotopic): 375.1471

AlogP: 5.09

#Rotatable Bonds: 4

Polar Surface Area: 68.39

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.03

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.63

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.65

Np Likeness Score: -0.32

References

1. Hasvold LA, Sheppard GS, Wang L, Fidanze SD, Liu D, Pratt JK, Mantei RA, Wada CK, Hubbard R, Shen Y, Lin X, Huang X, Warder SE, Wilcox D, Li L, Buchanan FG, Smithee L, Albert DH, Magoc TJ, Park CH, Petros AM, Panchal SC, Sun C, Kovar P, Soni NB, Elmore SW, Kati WM, McDaniel KF..  (2017)  Methylpyrrole inhibitors of BET bromodomains.,  27  (10): [PMID:28268136] [10.1016/j.bmcl.2017.02.057]

Source

Source(1):

• Scientific Literature