3-amino-6-(2,4-dimethoxyphenyl)-4-(furan-2-yl)thieno[2,3-b]pyridine-2-carboxamide

ID: ALA1090013

PubChem CID: 46884288

Max Phase: Preclinical

Molecular Formula: C20H17N3O4S

Molecular Weight: 395.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cc(-c3ccco3)c3c(N)c(C(N)=O)sc3n2)c(OC)c1

Standard InChI:  InChI=1S/C20H17N3O4S/c1-25-10-5-6-11(15(8-10)26-2)13-9-12(14-4-3-7-27-14)16-17(21)18(19(22)24)28-20(16)23-13/h3-9H,21H2,1-2H3,(H2,22,24)

Standard InChI Key:  LDJFUOXYSMNRKA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   16.1297  -15.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1266  -16.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8396  -16.8831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8418  -15.2319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5555  -15.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5529  -16.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3432  -16.7337    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.8343  -16.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3474  -15.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6047  -14.6039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6593  -16.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0696  -16.7804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0740  -15.3515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8414  -14.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5033  -13.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2479  -13.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4228  -13.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1685  -13.9225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4128  -16.8759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6994  -16.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9841  -16.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9810  -17.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6992  -18.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4115  -17.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1239  -18.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8386  -17.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2677  -18.1023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2661  -18.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
  4 14  1  0
 14 15  2  0
  1  2  2  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
  8  9  2  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
  8 11  1  0
 23 24  2  0
 24 19  1  0
  2 19  1  0
 11 12  2  0
 25 26  1  0
 24 25  1  0
  2  3  1  0
 11 13  1  0
 27 28  1  0
 22 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090013

   3-Amino-6-(2,4-dimethoxyphenyl)-4-(furan-2-yl)thieno[2,3-b]pyridine-2-carboxamide

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: 395.44

Molecular Weight (Monoisotopic): 395.0940

AlogP: 3.92

#Rotatable Bonds: 5

Polar Surface Area: 113.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: -1.39

References

1. Lockman JW, Reeder MD, Suzuki K, Ostanin K, Hoff R, Bhoite L, Austin H, Baichwal V, Adam Willardsen J..  (2010)  Inhibition of eEF2-K by thieno[2,3-b]pyridine analogues.,  20  (7): [PMID:20189382] [10.1016/j.bmcl.2010.02.005]

Source

Source(1):

• Scientific Literature