N-(3-(3-methyl-4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridin-1-yl)-4-phenoxyphenyl)methanesulfonamide

ID: ALA4087079

PubChem CID: 90387291

Max Phase: Preclinical

Molecular Formula: C21H21N3O4S

Molecular Weight: 411.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1[nH]c(-c2cc(NS(C)(=O)=O)ccc2Oc2ccccc2)c2c1C(=O)NCC2

Standard InChI:  InChI=1S/C21H21N3O4S/c1-13-19-16(10-11-22-21(19)25)20(23-13)17-12-14(24-29(2,26)27)8-9-18(17)28-15-6-4-3-5-7-15/h3-9,12,23-24H,10-11H2,1-2H3,(H,22,25)

Standard InChI Key:  ZGNLBROTMZIJBB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.5799  -28.4664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9967  -29.1833    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4091  -28.4638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4290  -28.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4278  -29.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1428  -29.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8595  -29.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8567  -28.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1410  -27.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1391  -27.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7226  -25.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4701  -26.6368    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355  -25.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5697  -27.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2860  -28.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2857  -29.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0011  -29.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7152  -29.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7094  -28.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9935  -27.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7129  -29.5976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2834  -29.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5479  -25.8488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8013  -26.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6034  -26.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1577  -26.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9043  -25.4107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0965  -25.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8418  -24.4508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
 10 24  2  0
 23 11  2  0
 11 12  1  0
 12 10  1  0
  9 10  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  5 21  1  0
 21  2  1  0
  2 22  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087079

   N-[3-(3-methyl-4-oxo-2,5,6,7-tetrahydropyrrolo[3,4-c]pyridin-1-yl)-4-phenoxyphenyl]methanesulfonamide

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: 411.48

Molecular Weight (Monoisotopic): 411.1253

AlogP: 3.44

#Rotatable Bonds: 5

Polar Surface Area: 100.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.05

CX Basic pKa: ┄

CX LogP: 1.81

CX LogD: 1.81

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -0.60

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