rac-N-(3,5-Dichlorophenyl)-4-[4-(trifluoromethyl)phenyl]-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxamide

ID: ALA4468307

PubChem CID: 155533073

Max Phase: Preclinical

Molecular Formula: C21H15Cl2F3N2OS

Molecular Weight: 471.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(Cl)cc(Cl)c1)N1CCc2sccc2C1c1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C21H15Cl2F3N2OS/c22-14-9-15(23)11-16(10-14)27-20(29)28-7-5-18-17(6-8-30-18)19(28)12-1-3-13(4-2-12)21(24,25)26/h1-4,6,8-11,19H,5,7H2,(H,27,29)

Standard InChI Key:  XKKLCGVIYVTODM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   27.0620  -25.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0620  -24.9671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3499  -24.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3504  -23.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0665  -23.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0668  -22.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3518  -22.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6349  -22.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6382  -23.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6379  -25.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6380  -24.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8490  -24.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3613  -25.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8489  -26.0484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.7776  -24.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4909  -24.9712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7801  -23.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2066  -24.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9166  -24.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6318  -24.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6346  -23.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9163  -23.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2041  -23.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3449  -24.9843    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   29.9158  -22.5040    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.3507  -21.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0647  -20.8383    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.6357  -20.8402    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.3463  -20.4253    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  3  4  1  0
  5  6  2  0
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 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
 21 25  1  0
 23 26  1  0
  8 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4468307

   ---

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: 471.33

Molecular Weight (Monoisotopic): 470.0234

AlogP: 7.25

#Rotatable Bonds: 2

Polar Surface Area: 32.34

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.74

CX Basic pKa: ┄

CX LogP: 6.87

CX LogD: 6.87

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -1.97

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