rac-2-(3,5-Dimethylphenyl)-1-[4-(4-methoxyphenyl)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl]ethan-1-one

ID: ALA4553576

PubChem CID: 155510420

Max Phase: Preclinical

Molecular Formula: C24H25NO2S

Molecular Weight: 391.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(C2c3ccsc3CCN2C(=O)Cc2cc(C)cc(C)c2)cc1

Standard InChI:  InChI=1S/C24H25NO2S/c1-16-12-17(2)14-18(13-16)15-23(26)25-10-8-22-21(9-11-28-22)24(25)19-4-6-20(27-3)7-5-19/h4-7,9,11-14,24H,8,10,15H2,1-3H3

Standard InChI Key:  RBLWDUVEFZBDKM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   28.4583  -16.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1703  -15.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1703  -15.0502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4583  -14.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4587  -13.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1749  -13.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1752  -12.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4602  -12.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7433  -12.5768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7465  -13.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7462  -15.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7463  -15.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9574  -14.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4696  -15.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9573  -16.1315    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.8860  -14.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5993  -15.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8885  -13.8148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3150  -14.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0249  -15.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7402  -14.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7430  -13.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0247  -13.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3125  -13.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4591  -11.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1730  -10.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0242  -12.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4532  -15.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12  4  1  0
 11  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  2  0
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  9 10  2  0
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  4  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 11  1  0
  3 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  8 25  1  0
 25 26  1  0
 23 27  1  0
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553576

   ---

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: 391.54

Molecular Weight (Monoisotopic): 391.1606

AlogP: 5.09

#Rotatable Bonds: 4

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.58

CX LogD: 5.58

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -1.25

References

1. Wortmann L, Lindenthal B, Muhn P, Walter A, Nubbemeyer R, Heldmann D, Sobek L, Morandi F, Schrey AK, Moosmayer D, Günther J, Kuhnke J, Koppitz M, Lücking U, Röhn U, Schäfer M, Nowak-Reppel K, Kühne R, Weinmann H, Langer G..  (2019)  Discovery of BAY-298 and BAY-899: Tetrahydro-1,6-naphthyridine-Based, Potent, and Selective Antagonists of the Luteinizing Hormone Receptor Which Reduce Sex Hormone Levels in Vivo.,  62  (22): [PMID:31670515] [10.1021/acs.jmedchem.9b01382]

Source

Source(1):

• Scientific Literature