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

ID: ALA5281552

Max Phase: Preclinical

Molecular Formula: C20H18N2O2S

Molecular Weight: 350.44

Names and Identifiers

Canonical SMILES:  O=C1c2scc(-c3cccnc3)c2CCN1C(CO)c1ccccc1

Standard InChI:  InChI=1S/C20H18N2O2S/c23-12-18(14-5-2-1-3-6-14)22-10-8-16-17(13-25-19(16)20(22)24)15-7-4-9-21-11-15/h1-7,9,11,13,18,23H,8,10,12H2

Standard InChI Key:  PBQVXLJBUDHUGU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.2848   -0.9101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4271    0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1391   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1436   -0.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9987   -1.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7138   -0.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9262   -1.1561    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9189    0.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4053   -0.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1324    0.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492    1.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7628    2.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5599    2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415    1.9817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9327    1.1842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9987   -2.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131   -2.5610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4278   -1.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403   -0.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1415   -0.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4320    0.3233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7150   -0.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  5  4  1  0
  3  6  1  0
  5  6  2  0
  3  7  2  0
  2  8  1  0
  8  9  1  0
  6 10  1  0
  5 11  1  0
 11 12  2  0
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 13 11  1  0
 14 13  2  0
 15 14  1  0
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 13 18  1  0
 18 17  2  0
  8 19  1  0
 19 20  1  0
 21  9  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
  9 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281552

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 350.44

Molecular Weight (Monoisotopic): 350.1089

AlogP: 3.54

#Rotatable Bonds: 4

Polar Surface Area: 53.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.63

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: -0.82

References

1. Tanaka Y, Kurasawa O, Yokota A, Klein MG, Saito B, Matsumoto S, Okaniwa M, Ambrus-Aikelin G, Uchiyama N, Morishita D, Kimura H, Imamura S..  (2020)  New Series of Potent Allosteric Inhibitors of Deoxyhypusine Synthase.,  11  (8.0): [PMID:34345355] [10.1021/acsmedchemlett.0c00331]

Source

Source(1):

• Scientific Literature