N-{3-[5-(2-Chloro-3-hydroxy-benzoyl)-thiophen-2-yl]-phenyl}-benzenesulfonamide

ID: ALA4574253

PubChem CID: 155564096

Max Phase: Preclinical

Molecular Formula: C23H16ClNO4S2

Molecular Weight: 469.97

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2cccc(NS(=O)(=O)c3ccccc3)c2)s1)c1cccc(O)c1Cl

Standard InChI:  InChI=1S/C23H16ClNO4S2/c24-22-18(10-5-11-19(22)26)23(27)21-13-12-20(30-21)15-6-4-7-16(14-15)25-31(28,29)17-8-2-1-3-9-17/h1-14,25-26H

Standard InChI Key:  BYONQZJFCLEVGK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.3480   -5.5552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0578   -5.1508    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.3526   -4.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5454   -4.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5442   -5.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2523   -5.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9619   -5.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9591   -4.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2505   -4.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2480   -3.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9545   -3.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5391   -3.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7006   -3.4419    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.2456   -2.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8348   -2.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0361   -2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8362   -5.9738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0568   -2.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3906   -3.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2028   -3.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6821   -3.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3433   -2.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5321   -2.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5371   -4.4904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3926   -5.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9111   -6.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2447   -7.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0584   -7.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5375   -6.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2012   -5.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8376   -4.3378    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 30 25  1  0
  4 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4574253

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 469.97

Molecular Weight (Monoisotopic): 469.0209

AlogP: 5.81

#Rotatable Bonds: 6

Polar Surface Area: 83.47

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.28

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 5.37

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -1.20

References

1. Abdelsamie AS, Herath S, Biskupek Y, Börger C, Siebenbürger L, Salah M, Scheuer C, Marchais-Oberwinkler S, Frotscher M, Pohlemann T, Menger MD, Hartmann RW, Laschke MW, van Koppen CJ..  (2019)  Targeted Endocrine Therapy: Design, Synthesis, and Proof-of-Principle of 17β-Hydroxysteroid Dehydrogenase Type 2 Inhibitors in Bone Fracture Healing.,  62  (3): [PMID:30645111] [10.1021/acs.jmedchem.8b01493]

Source

Source(1):

• Scientific Literature