1,1,1,3,3,3-Hexafluoro-2-(4-((2S)-2-(4-morpholinylmethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

ID: ALA3127348

PubChem CID: 76311063

Max Phase: Preclinical

Molecular Formula: C22H25F6N3O4S2

Molecular Weight: 573.58

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)[C@@H](CN2CCOCC2)C1

Standard InChI:  InChI=1S/C22H25F6N3O4S2/c23-21(24,25)20(32,22(26,27)28)16-3-5-17(6-4-16)31-8-7-30(37(33,34)19-2-1-13-36-19)15-18(31)14-29-9-11-35-12-10-29/h1-6,13,18,32H,7-12,14-15H2/t18-/m0/s1

Standard InChI Key:  QAIPKSPQMAFRIQ-SFHVURJKSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    2.1621   -2.4595    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1570   -1.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4451   -2.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -1.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871   -2.4544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4030   -3.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2237   -3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328   -2.4440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2211   -1.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4566   -2.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8698   -3.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6940   -3.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1060   -2.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6877   -1.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8648   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9310   -2.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3458   -3.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3411   -1.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7540   -2.4374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1661   -1.7194    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9263   -1.0089    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7458   -1.0042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9356   -3.8667    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.1708   -3.1484    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7540   -3.8624    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -3.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -3.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634   -4.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4805   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0901   -3.9303    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386   -3.8735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2286   -4.5894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4044   -4.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9944   -5.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4093   -6.0189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387   -6.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6449   -5.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  4  9  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 18 20  1  0
 18 21  1  0
 18 22  1  0
 17 23  1  0
 17 24  1  0
 17 25  1  0
  5  1  1  0
  1 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 26  1  0
  7 31  1  1
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3127348

   1,1,1,3,3,3-hexafluoro-2-[4-[(2S)-2-(morpholin-4-ylmethyl)-4-thiophen-2-ylsulfonylpiperazin-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: 573.58

Molecular Weight (Monoisotopic): 573.1191

AlogP: 3.27

#Rotatable Bonds: 6

Polar Surface Area: 73.32

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.52

CX Basic pKa: 6.12

CX LogP: 3.52

CX LogD: 3.42

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.54

Np Likeness Score: -1.67

References

1. 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