Propane-1-sulfonic acid {2,4-difluoro-3-[5-(3-methoxy-prop-1-ynyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide

ID: ALA3945707

PubChem CID: 49779974

Max Phase: Preclinical

Molecular Formula: C21H19F2N3O4S

Molecular Weight: 447.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCS(=O)(=O)Nc1ccc(F)c(C(=O)c2c[nH]c3ncc(C#CCOC)cc23)c1F

Standard InChI:  InChI=1S/C21H19F2N3O4S/c1-3-9-31(28,29)26-17-7-6-16(22)18(19(17)23)20(27)15-12-25-21-14(15)10-13(11-24-21)5-4-8-30-2/h6-7,10-12,26H,3,8-9H2,1-2H3,(H,24,25)

Standard InChI Key:  YGVMSLDTJJETDU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.2116   -3.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2397   -4.1685    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9353   -3.7345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3741   -3.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3723   -4.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0803   -4.9512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0786   -3.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7872   -3.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920   -4.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5764   -4.7921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0564   -4.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5686   -3.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9770   -2.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7942   -2.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5687   -2.0452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1998   -3.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0162   -3.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4259   -2.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0131   -2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1981   -2.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7868   -1.3411    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7895   -4.1689    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.4242   -4.1708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6494   -4.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4665   -4.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8745   -5.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6665   -3.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9551   -2.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2452   -2.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5380   -2.9024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298   -2.4947    0.0000 C   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
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 20 21  1  0
 16 22  1  0
 17 23  1  0
 23  2  1  0
  2 24  1  0
 24 25  1  0
 25 26  1  0
  4 27  1  0
 27 28  3  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3945707

   N-[2,4-difluoro-3-[5-(3-methoxyprop-1-ynyl)-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: 447.46

Molecular Weight (Monoisotopic): 447.1064

AlogP: 3.22

#Rotatable Bonds: 7

Polar Surface Area: 101.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.87

CX Basic pKa: 1.62

CX LogP: 2.72

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: -1.28

References

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

Source

Source(1):

• Patent Bioactivity Data