(5-(3,5-Dichloro-4-methoxy-phenyl)-thiophen-2-yl)-(3-hydroxy-phenyl)-methanone

ID: ALA4089862

PubChem CID: 137644465

Max Phase: Preclinical

Molecular Formula: C18H12Cl2O3S

Molecular Weight: 379.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(Cl)cc(-c2ccc(C(=O)c3cccc(O)c3)s2)cc1Cl

Standard InChI:  InChI=1S/C18H12Cl2O3S/c1-23-18-13(19)8-11(9-14(18)20)15-5-6-16(24-15)17(22)10-3-2-4-12(21)7-10/h2-9,21H,1H3

Standard InChI Key:  ZHTGNWVMKZKUIM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   23.0625  -11.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8875  -11.7292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.1442  -10.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4750  -10.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8099  -10.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9254  -10.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5377  -11.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3220  -10.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4953  -10.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8780   -9.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0960   -9.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5767  -12.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7563  -12.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9112  -13.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4236  -13.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7576  -14.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5788  -14.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0650  -13.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7284  -13.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2715  -15.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9341  -11.5444    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.0478   -8.8226    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.2799   -9.9288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8930  -10.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3  6  1  0
  1 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
  8 21  1  0
 10 22  1  0
  9 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089862

   ---

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: 379.26

Molecular Weight (Monoisotopic): 377.9884

AlogP: 5.67

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.85

CX Basic pKa: ┄

CX LogP: 5.74

CX LogD: 5.72

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.59

Np Likeness Score: -0.38

References

1. Abdelsamie AS, van Koppen CJ, Bey E, Salah M, Börger C, Siebenbürger L, Laschke MW, Menger MD, Frotscher M..  (2017)  Treatment of estrogen-dependent diseases: Design, synthesis and profiling of a selective 17β-HSD1 inhibitor with sub-nanomolar IC50 for a proof-of-principle study.,  127  [PMID:27852458] [10.1016/j.ejmech.2016.11.004]

Source

Source(1):

• Scientific Literature