(S)-3-chloro-4-(4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)phenylsulfonyl)benzonitrile

ID: ALA3357071

PubChem CID: 49870852

Max Phase: Preclinical

Molecular Formula: C16H11ClF3NO3S

Molecular Weight: 389.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@](O)(c1ccc(S(=O)(=O)c2ccc(C#N)cc2Cl)cc1)C(F)(F)F

Standard InChI:  InChI=1S/C16H11ClF3NO3S/c1-15(22,16(18,19)20)11-3-5-12(6-4-11)25(23,24)14-7-2-10(9-21)8-13(14)17/h2-8,22H,1H3/t15-/m0/s1

Standard InChI Key:  UMQOWWADXICFNS-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    4.1568  -10.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473   -9.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4469   -7.4067    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704   -9.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2893   -9.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8732   -9.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263   -7.4070    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5821  -10.2818    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7369   -8.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7141   -9.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7367   -7.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -6.9983    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9864  -10.9901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4461   -9.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1348   -8.2271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0003  -11.1038    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0236   -8.2276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1550   -8.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4247   -8.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -9.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9976   -8.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2940   -9.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0020  -10.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1692  -10.9876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7133   -9.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  2 14  2  0
  9 17  1  0
  5 22  1  0
 25 10  2  0
 22 23  2  0
 10 19  1  0
 23 16  1  0
  6  4  1  0
 24  8  2  0
 23 25  1  0
 10 21  1  0
 11 12  1  0
  9 11  1  1
 11  3  1  0
  8 22  1  0
  4 18  2  0
  1  6  2  0
  6  8  1  0
 21  5  2  0
 14  1  1  0
  8 13  2  0
 19 15  3  0
  9 20  1  0
 11  7  1  0
 18  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3357071

   3-chloro-4-[4-[(2S)-1,1,1-trifluoro-2-hydroxypropan-2-yl]phenyl]sulfonylbenzonitrile

2. Alternative Forms:

   

   ALA3357071

   ---

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: 389.78

Molecular Weight (Monoisotopic): 389.0100

AlogP: 3.81

#Rotatable Bonds: 3

Polar Surface Area: 78.16

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.63

CX Basic pKa: ┄

CX LogP: 3.92

CX LogD: 3.92

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: -1.48

References

1. Sun D, Ye Q, Yan X, Rew Y, Fan P, He X, Jiang M, McMinn DL, Monshouwer M, Tu H, Powers JP..  (2014)  Synthesis, in Vitro Covalent Binding Evaluation, and Metabolism of (14)C-Labeled Inhibitors of 11β-HSD1.,  5  (11): [PMID:25408839] [10.1021/ml500331y]

Source

Source(1):

• Scientific Literature