2-(2-(4-((6-Amino-3-pyridinyl)sulfonyl)-2-(1-propyn-1-yl)-1-piperazinyl)-1,3-thiazol-5-yl)-1,1,1-trifluoro-2-propanol

ID: ALA3238316

PubChem CID: 90655472

Max Phase: Preclinical

Molecular Formula: C18H20F3N5O3S2

Molecular Weight: 475.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#C[C@H]1CN(S(=O)(=O)c2ccc(N)nc2)CCN1c1ncc(C(C)(O)C(F)(F)F)s1

Standard InChI:  InChI=1S/C18H20F3N5O3S2/c1-3-4-12-11-25(31(28,29)13-5-6-15(22)23-9-13)7-8-26(12)16-24-10-14(30-16)17(2,27)18(19,20)21/h5-6,9-10,12,27H,7-8,11H2,1-2H3,(H2,22,23)/t12-,17?/m0/s1

Standard InChI Key:  SEUGHLRWPCHHBJ-WHUIICBVSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   19.8388  -16.0103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5137  -18.8671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2200  -18.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0977  -21.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9300  -20.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5121  -18.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5119  -19.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2877  -15.3106    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.6388  -20.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5388  -15.3435    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.8050  -20.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6787  -21.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8023  -18.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4373  -16.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3880  -23.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3039  -17.6439    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.0930  -19.6914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3882  -22.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2537  -16.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0891  -18.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6775  -22.1589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9713  -19.3856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1360  -16.1466    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.3864  -20.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1019  -17.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1006  -22.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2200  -20.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9523  -16.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9633  -18.7890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3802  -20.0981    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5593  -20.0939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3 29  2  0
 18 26  2  0
  5  9  1  0
 24 12  1  0
 22 30  2  0
  7  2  1  0
 30 31  2  0
 13 20  1  0
 29  6  1  0
 17 11  1  0
  2  3  1  0
  2 13  1  0
 17 20  1  0
 27  5  3  0
 28  8  1  0
 25 16  1  0
 21 18  1  0
 30 17  1  0
  7 27  1  1
 11  7  1  0
 28 10  1  0
 16  3  1  0
 24 30  1  0
 25 14  1  0
 28 23  1  0
 12 21  2  0
  6 25  2  0
 14 28  1  0
 14 19  1  0
  4 24  2  0
 26  4  1  0
 14  1  1  0
 18 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3238316

   2-[2-[(2S)-4-(6-aminopyridin-3-yl)sulfonyl-2-prop-1-ynylpiperazin-1-yl]-1,3-thiazol-5-yl]-1,1,1-trifluoropropan-2-ol

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: 475.52

Molecular Weight (Monoisotopic): 475.0960

AlogP: 1.79

#Rotatable Bonds: 4

Polar Surface Area: 112.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.23

CX Basic pKa: 3.22

CX LogP: 2.44

CX LogD: 2.44

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.65

Np Likeness Score: -0.83

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