4-tert-Butyl-N-(3-hydroxy-phenyl)-benzenesulfonamide

ID: ALA185823

Cas Number: 692763-14-7

PubChem CID: 701308

Max Phase: Preclinical

Molecular Formula: C16H19NO3S

Molecular Weight: 305.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(S(=O)(=O)Nc2cccc(O)c2)cc1

Standard InChI:  InChI=1S/C16H19NO3S/c1-16(2,3)12-7-9-15(10-8-12)21(19,20)17-13-5-4-6-14(18)11-13/h4-11,17-18H,1-3H3

Standard InChI Key:  PFOZVVVJWABLDF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    0.4542   -0.5042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -0.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542    0.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -1.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0125   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250    0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6083    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667    0.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042    1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250    0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2500   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375    1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  2  0
  5  1  2  0
  6  7  1  0
  7 12  1  0
  8  2  1  0
  9  8  2  0
 10  3  2  0
 11  3  1  0
 12 11  2  0
 13 10  1  0
 14  9  1  0
 15 14  1  0
 16 20  2  0
 17  6  1  0
 18  6  1  0
 19  6  1  0
 20  8  1  0
 21 16  1  0
 13  7  2  0
 14 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA185823

   4-tert-butyl-N-(3-hydroxyphenyl)benzenesulfonamide

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: 305.40

Molecular Weight (Monoisotopic): 305.1086

AlogP: 3.49

#Rotatable Bonds: 3

Polar Surface Area: 66.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.82

CX Basic pKa: ┄

CX LogP: 3.70

CX LogD: 3.58

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.91

Np Likeness Score: -1.27

References

1. Natarajan A, Guo Y, Harbinski F, Fan YH, Chen H, Luus L, Diercks J, Aktas H, Chorev M, Halperin JA..  (2004)  Novel arylsulfoanilide-oxindole hybrid as an anticancer agent that inhibits translation initiation.,  47  (21): [PMID:15456240] [10.1021/jm0496234]

2. Jung HJ, Cho M, Kim Y, Han G, Kwon HJ..  (2014)  Development of a novel class of mitochondrial ubiquinol-cytochrome c reductase binding protein (UQCRB) modulators as promising antiangiogenic leads.,  57  (19): [PMID:25244355] [10.1021/jm500863j]

3. Choi E, Lee J, Lee S, Song BW, Seo HH, Cha MJ, Lim S, Lee C, Song SW, Han G, Hwang KC..  (2016)  Potential therapeutic application of small molecule with sulfonamide for chondrogenic differentiation and articular cartilage repair.,  26  (20): [PMID:27614412] [10.1016/j.bmcl.2016.08.069]

Source

Source(1):

• Scientific Literature