2-(5-bromo-2-methyl-1-(4-(methylsulfonyl)benzyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

ID: ALA4102679

PubChem CID: 137656723

Max Phase: Preclinical

Molecular Formula: C18H17BrN2O4S

Molecular Weight: 437.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(CC(=O)O)c2cc(Br)cnc2n1Cc1ccc(S(C)(=O)=O)cc1

Standard InChI:  InChI=1S/C18H17BrN2O4S/c1-11-15(8-17(22)23)16-7-13(19)9-20-18(16)21(11)10-12-3-5-14(6-4-12)26(2,24)25/h3-7,9H,8,10H2,1-2H3,(H,22,23)

Standard InChI Key:  IKHYFMLBVROBQK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   15.0272   -7.3300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6228   -6.6242    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.2138   -7.3274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7925   -4.1817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4535   -3.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1983   -2.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2310   -3.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6758   -2.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4889   -2.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9664   -1.6775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8245   -3.0858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7938   -4.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5022   -5.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4999   -6.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2075   -6.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9155   -6.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9115   -5.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2034   -4.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3309   -6.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1300   -3.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3828   -2.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8403   -2.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0448   -2.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7948   -3.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3390   -3.8725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4973   -1.8884    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
 20  4  1  0
  4  5  1  0
  5  6  2  0
  6 21  1  0
  5  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16  2  1  0
  2 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102679

   ---

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: 437.32

Molecular Weight (Monoisotopic): 436.0092

AlogP: 3.19

#Rotatable Bonds: 5

Polar Surface Area: 89.26

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.40

CX Basic pKa: 1.64

CX LogP: 2.45

CX LogD: -0.79

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.39

References

1. Sandham DA, Barker L, Brown L, Brown Z, Budd D, Charlton SJ, Chatterjee D, Cox B, Dubois G, Duggan N, Hall E, Hatto J, Maas J, Manini J, Profit R, Riddy D, Ritchie C, Sohal B, Shaw D, Stringer R, Sykes DA, Thomas M, Turner KL, Watson SJ, West R, Willard E, Williams G, Willis J..  (2017)  Discovery of Fevipiprant (NVP-QAW039), a Potent and Selective DP2 Receptor Antagonist for Treatment of Asthma.,  8  (5): [PMID:28523115] [10.1021/acsmedchemlett.7b00157]

Source

Source(1):

• Scientific Literature