N-(4-(4-Chlorophenoxy)-3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)-ethanesulfonamide

ID: ALA4098055

PubChem CID: 137659228

Max Phase: Preclinical

Molecular Formula: C22H20ClN3O4S

Molecular Weight: 457.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)Nc1ccc(Oc2ccc(Cl)cc2)c(-c2cn(C)c(=O)c3[nH]ccc23)c1

Standard InChI:  InChI=1S/C22H20ClN3O4S/c1-3-31(28,29)25-15-6-9-20(30-16-7-4-14(23)5-8-16)18(12-15)19-13-26(2)22(27)21-17(19)10-11-24-21/h4-13,24-25H,3H2,1-2H3

Standard InChI Key:  ILIBVZQYUORVEK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   27.1695  -20.5949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5823  -21.3089    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.9948  -20.5924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0089  -20.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0077  -21.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7199  -21.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4337  -21.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4309  -20.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7181  -20.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1412  -20.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8504  -20.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8501  -21.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5627  -21.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2739  -21.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2682  -20.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5551  -20.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7118  -19.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7125  -17.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.7132  -16.7961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2885  -17.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4238  -18.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4203  -18.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1946  -19.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6741  -18.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2002  -17.7805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.2956  -21.7234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8719  -21.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1594  -21.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9879  -21.7012    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  5  2  0
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 18 19  1  0
 19 20  1  0
  9 17  1  0
 18 21  2  0
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 24 25  1  0
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 26 27  1  0
 27 23  1  0
  5 28  1  0
 28  2  1  0
  2 29  1  0
 29 30  1  0
 14 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098055

   ---

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: 457.94

Molecular Weight (Monoisotopic): 457.0863

AlogP: 4.74

#Rotatable Bonds: 6

Polar Surface Area: 93.19

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.37

CX Basic pKa: ┄

CX LogP: 2.97

CX LogD: 2.97

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: -1.07

References

1. McDaniel KF, Wang L, Soltwedel T, Fidanze SD, Hasvold LA, Liu D, Mantei RA, Pratt JK, Sheppard GS, Bui MH, Faivre EJ, Huang X, Li L, Lin X, Wang R, Warder SE, Wilcox D, Albert DH, Magoc TJ, Rajaraman G, Park CH, Hutchins CW, Shen JJ, Edalji RP, Sun CC, Martin R, Gao W, Wong S, Fang G, Elmore SW, Shen Y, Kati WM..  (2017)  Discovery of N-(4-(2,4-Difluorophenoxy)-3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)ethanesulfonamide (ABBV-075/Mivebresib), a Potent and Orally Available Bromodomain and Extraterminal Domain (BET) Family Bromodomain Inhibitor.,  60  (20): [PMID:28949521] [10.1021/acs.jmedchem.7b00746]

Source

Source(1):

• Scientific Literature