(2R)-2-(4-((2S)-4-((6-Amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)phenyl)-3,3,3-trifluoro-1,2-propanediol

ID: ALA3237981

PubChem CID: 89761004

Max Phase: Preclinical

Molecular Formula: C21H23F3N4O4S

Molecular Weight: 484.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#C[C@H]1CN(S(=O)(=O)c2ccc(N)nc2)CCN1c1ccc([C@@](O)(CO)C(F)(F)F)cc1

Standard InChI:  InChI=1S/C21H23F3N4O4S/c1-2-3-17-13-27(33(31,32)18-8-9-19(25)26-12-18)10-11-28(17)16-6-4-15(5-7-16)20(30,14-29)21(22,23)24/h4-9,12,17,29-30H,10-11,13-14H2,1H3,(H2,25,26)/t17-,20-/m0/s1

Standard InChI Key:  HZYIALCWDCIMRP-PXNSSMCTSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    4.7583   -8.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5833   -8.9750    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1744   -8.2584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8777  -10.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8765  -11.0439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5914  -11.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3077  -11.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3049  -10.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5895   -9.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3003   -8.5642    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0162   -8.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7274   -8.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292   -7.7356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0136   -7.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2963   -7.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1538   -7.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8682   -7.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8692   -6.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1501   -6.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4388   -6.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912  -12.2817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4395   -8.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1535   -9.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8624   -9.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5835   -6.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2982   -6.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5831   -5.2654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2973   -4.8525    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8684   -4.8532    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5749   -4.4375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.2986   -7.3275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2957   -5.6708    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  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  9  2  1  0
  2 10  1  0
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 16  1  0
  6 22  1  0
 23 24  3  0
 12 23  1  1
 24 25  1  0
 19 26  1  0
 26 27  1  0
 26 28  1  6
 28 29  1  0
 28 30  1  0
 28 31  1  0
 27 32  1  0
 26 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3237981

   CID 89761004

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: 484.50

Molecular Weight (Monoisotopic): 484.1392

AlogP: 1.31

#Rotatable Bonds: 5

Polar Surface Area: 119.99

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.99

CX Basic pKa: 2.68

CX LogP: 1.92

CX LogD: 1.92

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.55

Np Likeness Score: -0.86

References

1. Nishimura N, Norman MH, Liu L, Yang KC, Ashton KS, Bartberger MD, Chmait S, Chen J, Cupples R, Fotsch C, Helmering J, Jordan SR, Kunz RK, Pennington LD, Poon SF, Siegmund A, Sivits G, Lloyd DJ, Hale C, St Jean DJ..  (2014)  Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 3. Structure-activity relationships within the aryl carbinol region of the N-arylsulfonamido-N'-arylpiperazine series.,  57  (7): [PMID:24611879] [10.1021/jm5000497]

Source

Source(1):

• Scientific Literature