1,1,1,3,3,3-hexafluoro-2-(4-(4-(thiophen-2-ylsulfonyl)piperazin-1-yl)phenyl)propan-2-ol

ID: ALA3113992

PubChem CID: 56832521

Max Phase: Preclinical

Molecular Formula: C17H16F6N2O3S2

Molecular Weight: 474.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(c1cccs1)N1CCN(c2ccc(C(O)(C(F)(F)F)C(F)(F)F)cc2)CC1

Standard InChI:  InChI=1S/C17H16F6N2O3S2/c18-16(19,20)15(26,17(21,22)23)12-3-5-13(6-4-12)24-7-9-25(10-8-24)30(27,28)14-2-1-11-29-14/h1-6,11,26H,7-10H2

Standard InChI Key:  FTXKDYBMOPKENQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.6658   -4.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4896   -4.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9027   -4.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4891   -3.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6622   -3.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2569   -4.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7282   -4.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1387   -4.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1391   -3.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9646   -3.5202    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7286   -2.8044    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.5490   -2.8001    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.5531   -4.2313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4329   -4.2383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0172   -3.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1953   -3.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7829   -4.2376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1944   -4.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0226   -4.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9573   -4.2369    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5420   -4.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1317   -4.2355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383   -3.5178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7203   -5.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489   -5.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2641   -6.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8748   -5.7015    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7279   -5.6580    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9601   -4.9470    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.5448   -5.6542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
  9 12  1  0
  7 13  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  6 14  1  0
 17 20  1  0
 20 21  1  0
 20 22  2  0
 20 23  2  0
 21 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 21  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3113992

   1,1,1,3,3,3-Hexafluoro-2-{4-[4-(Thiophen-2-Ylsulfonyl)piperazin-1-Yl]phenyl}propan-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: 474.45

Molecular Weight (Monoisotopic): 474.0507

AlogP: 3.57

#Rotatable Bonds: 4

Polar Surface Area: 60.85

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.51

CX Basic pKa: 2.13

CX LogP: 3.84

CX LogD: 3.59

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: -1.77

References

1. St Jean DJ, Ashton KS, Bartberger MD, Chen J, Chmait S, Cupples R, Galbreath E, Helmering J, Hong FT, Jordan SR, Liu L, Kunz RK, Michelsen K, Nishimura N, Pennington LD, Poon SF, Reid D, Sivits G, Stec MM, Tadesse S, Tamayo N, Van G, Yang KC, Zhang J, Norman MH, Fotsch C, Lloyd DJ, Hale C..  (2014)  Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 2. Leveraging structure-based drug design to identify analogues with improved pharmacokinetic profiles.,  57  (2): [PMID:24405213] [10.1021/jm4016747]

2. Ashton KS, Andrews KL, Bryan MC, Chen J, Chen K, Chen M, Chmait S, Croghan M, Cupples R, Fotsch C, Helmering J, Jordan SR, Kurzeja RJ, Michelsen K, Pennington LD, Poon SF, Sivits G, Van G, Vonderfecht SL, Wahl RC, Zhang J, Lloyd DJ, Hale C, St Jean DJ..  (2014)  Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 1. Discovery of a novel tool compound for in vivo proof-of-concept.,  57  (2): [PMID:24405172] [10.1021/jm4016735]

Source

Source(1):

• Scientific Literature