2-(6-(4-((6-Aminopyridin-3-yl)sulfonyl)piperazin-1-yl)-5-(furan-3-yl)pyridin-3-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol

ID: ALA3319539

PubChem CID: 118709629

Max Phase: Preclinical

Molecular Formula: C21H19F6N5O4S

Molecular Weight: 551.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(S(=O)(=O)N2CCN(c3ncc(C(O)(C(F)(F)F)C(F)(F)F)cc3-c3ccoc3)CC2)cn1

Standard InChI:  InChI=1S/C21H19F6N5O4S/c22-20(23,24)19(33,21(25,26)27)14-9-16(13-3-8-36-12-13)18(30-10-14)31-4-6-32(7-5-31)37(34,35)15-1-2-17(28)29-11-15/h1-3,8-12,33H,4-7H2,(H2,28,29)

Standard InChI Key:  QGQJZMHESTYQND-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    9.2863  -29.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1035  -29.0144    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6984  -28.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4045  -30.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4034  -31.0638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1114  -31.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8211  -31.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8183  -30.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1096  -29.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1112  -32.2900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8137  -28.6075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5268  -29.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2312  -28.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2330  -27.7892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5242  -27.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8137  -27.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9382  -27.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6459  -27.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3535  -27.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.6422  -26.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9376  -26.5698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0620  -26.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7700  -26.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0616  -25.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7660  -25.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7704  -27.3855    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.4775  -26.1594    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.4718  -26.9756    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7691  -24.9340    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.3537  -24.9347    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0561  -24.5240    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6464  -28.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9916  -29.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2432  -29.8587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0562  -29.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3068  -29.0850    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  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  6 10  1  0
  9  2  1  0
  2 11  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  0
 20 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 24 27  1  0
 24 28  1  0
 24 29  1  0
 25 30  1  0
 25 31  1  0
 25 32  1  0
 18 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 37 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3319539

   ---

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: 551.47

Molecular Weight (Monoisotopic): 551.1062

AlogP: 3.14

#Rotatable Bonds: 5

Polar Surface Area: 125.79

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.30

CX Basic pKa: 5.32

CX LogP: 2.50

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.46

Np Likeness Score: -0.88

References

1. Hong FT, Norman MH, Ashton KS, Bartberger MD, Chen J, Chmait S, Cupples R, Fotsch C, Jordan SR, Lloyd DJ, Sivits G, Tadesse S, Hale C, St Jean DJ..  (2014)  Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 4. Exploration of a novel binding pocket.,  57  (14): [PMID:25001129] [10.1021/jm5001979]

Source

Source(1):

• Scientific Literature