Propane-1-sulfonic acid {2,4-difluoro-3-[5-(6-hydroxy-pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide

ID: ALA3961672

PubChem CID: 49779914

Max Phase: Preclinical

Molecular Formula: C22H18F2N4O4S

Molecular Weight: 472.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCS(=O)(=O)Nc1ccc(F)c(C(=O)c2c[nH]c3ncc(-c4ccc(O)nc4)cc23)c1F

Standard InChI:  InChI=1S/C22H18F2N4O4S/c1-2-7-33(31,32)28-17-5-4-16(23)19(20(17)24)21(30)15-11-27-22-14(15)8-13(10-26-22)12-3-6-18(29)25-9-12/h3-6,8-11,28H,2,7H2,1H3,(H,25,29)(H,26,27)

Standard InChI Key:  MKVMMAUBKKDDSE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   24.9541  -17.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9821  -18.1722    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.6777  -17.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1166  -17.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1148  -18.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8228  -18.9549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8210  -17.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5296  -17.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5345  -18.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3188  -18.7958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7988  -18.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.7586  -17.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1683  -16.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7556  -16.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9405  -16.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5292  -15.3448    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.5320  -18.1726    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.1666  -18.1745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3918  -18.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2090  -18.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6170  -19.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4119  -17.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4135  -16.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7067  -16.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9979  -16.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0003  -17.3234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7077  -17.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2898  -16.0941    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  9  2  0
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  7  4  1  0
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  9 10  1  0
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 20 21  1  0
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 23  2  1  0
  2 24  1  0
 24 25  1  0
 25 26  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 27  2  0
  4 27  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3961672

   N-[2,4-difluoro-3-[5-(6-oxo-1H-pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenyl]propane-1-sulfonamide

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: 472.47

Molecular Weight (Monoisotopic): 472.1017

AlogP: 3.99

#Rotatable Bonds: 7

Polar Surface Area: 125.04

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: 2.39

CX LogP: 3.09

CX LogD: 3.08

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.35

Np Likeness Score: -1.25

References

1.  (2012)  Compounds and methods for kinase modulation, and indications thereof, 

Source

Source(1):

• Patent Bioactivity Data