N-{3-[5-(4-Chloro-3-hydroxybenzoyl)thiophen-2-yl]phenyl}-benzenesulfonamide

ID: ALA4519897

PubChem CID: 155542289

Max Phase: Preclinical

Molecular Formula: C23H16ClNO4S2

Molecular Weight: 469.97

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(Cl)c(O)c1)c1ccc(-c2cccc(NS(=O)(=O)c3ccccc3)c2)s1

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

Standard InChI Key:  PJWQHMPSYVIIQW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.9381  -11.7378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6480  -11.3334    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9428  -10.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1355  -10.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1344  -11.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8425  -12.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5521  -11.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5493  -10.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8407  -10.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382   -9.7028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5447   -9.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1293   -9.2963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2908   -9.6245    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.8358   -9.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4250   -8.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6263   -8.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4264  -12.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6470   -9.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9808   -9.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7930   -9.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2722   -9.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9335   -8.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1223   -8.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1273  -10.6730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9828  -12.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5013  -12.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8349  -13.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6486  -13.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1277  -12.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7914  -12.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8423  -12.9746    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
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  5 17  1  0
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 14 18  1  0
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  2 25  1  0
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 28 29  1  0
 29 30  2  0
 30 25  1  0
  6 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4519897

   ---

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: 7.20

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 5.32

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -1.26

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