4-chloro-N-(4-fluoro-3-(2-isopropyl-6-methyl-1,3-dioxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-4-yloxy)phenyl)benzenesulfonamide

ID: ALA3104879

PubChem CID: 72946092

Max Phase: Preclinical

Molecular Formula: C23H19ClFN3O5S

Molecular Weight: 503.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(c(Oc3cc(NS(=O)(=O)c4ccc(Cl)cc4)ccc3F)n1)C(=O)N(C(C)C)C2=O

Standard InChI:  InChI=1S/C23H19ClFN3O5S/c1-12(2)28-22(29)17-10-13(3)26-21(20(17)23(28)30)33-19-11-15(6-9-18(19)25)27-34(31,32)16-7-4-14(24)5-8-16/h4-12,27H,1-3H3

Standard InChI Key:  ZMXPRLZLGHHSKI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.3142  -17.1633    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7272  -16.4492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9022  -16.4485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7442  -16.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7431  -17.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4579  -17.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1743  -17.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1715  -16.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4561  -15.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0284  -17.5764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994  -17.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861  -17.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1718  -17.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707  -18.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6012  -18.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565  -18.8099    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8894  -17.5753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3073  -15.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5970  -16.3389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0283  -17.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3193  -17.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4941  -18.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3114  -18.4589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6414  -17.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9453  -18.9932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4474  -17.5312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3031  -15.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7276  -19.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3188  -19.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5526  -19.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8843  -15.9183    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
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 14 17  1  0
  7 18  1  0
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 20 21  2  0
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 23 24  2  0
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 26 27  1  0
 27 23  1  0
 25 28  2  0
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 21 30  1  0
 26 31  1  0
 31 32  1  0
 31 33  1  0
  8 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3104879

   4-chloro-N-[4-fluoro-3-(6-methyl-1,3-dioxo-2-propan-2-ylpyrrolo[3,4-c]pyridin-4-yl)oxyphenyl]benzenesulfonamide

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: 503.94

Molecular Weight (Monoisotopic): 503.0718

AlogP: 4.78

#Rotatable Bonds: 6

Polar Surface Area: 105.67

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.79

CX Basic pKa: 0.80

CX LogP: 3.93

CX LogD: 3.80

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.49

Np Likeness Score: -1.75

References

1. Yu M, Ken Zhang J, Wang Y, Zhu J, Kayser F, Medina JC, Siegler K, Conn M, Shan B, Grillo MP, Coward P, Jim Liu J..  (2014)  Discovery and optimization of N-(3-(1,3-dioxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-4-yloxy)phenyl)benzenesulfonamides as novel GPR119 agonists.,  24  (1): [PMID:24332491] [10.1016/j.bmcl.2013.11.053]

Source

Source(1):

• Scientific Literature