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

ID: ALA5282634

Max Phase: Preclinical

Molecular Formula: C22H20N4OS

Molecular Weight: 388.50

Names and Identifiers

Canonical SMILES:  NCC(c1c[nH]c2ccccc12)N1CCc2c(-c3cccnc3)csc2C1=O

Standard InChI:  InChI=1S/C22H20N4OS/c23-10-20(17-12-25-19-6-2-1-5-15(17)19)26-9-7-16-18(13-28-21(16)22(26)27)14-4-3-8-24-11-14/h1-6,8,11-13,20,25H,7,9-10,23H2

Standard InChI Key:  XSYKKVGKKRLWNG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    0.1831   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831   -0.9101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951   -1.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6117   -0.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6071   -0.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951    0.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    0.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8735   -0.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -1.1561    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6005    0.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0173    1.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309    2.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0279    2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6095    1.9817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007    1.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -2.1435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -1.3237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457   -0.9122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -2.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451   -2.5611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -1.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5511   -0.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399    0.0779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331   -0.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2519   -2.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0583   -2.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6096   -1.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3609   -0.8103    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  1  0
  5  4  2  0
  5  6  1  0
  1  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  1  0
 10  7  1  0
 11 10  2  0
 12 11  1  0
 13 12  2  0
 14 13  1  0
 15 14  2  0
 10 15  1  0
  3 16  2  0
  2 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 21 18  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 18  2  0
 21 25  1  0
 26 25  2  0
 27 26  1  0
 28 27  2  0
 22 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282634

   ---

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: 388.50

Molecular Weight (Monoisotopic): 388.1358

AlogP: 3.99

#Rotatable Bonds: 4

Polar Surface Area: 75.01

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.67

CX LogP: 2.74

CX LogD: 1.45

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -0.76

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