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

ID: ALA1089298

PubChem CID: 46884358

Max Phase: Preclinical

Molecular Formula: C19H21N3O2S

Molecular Weight: 355.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1sc2nc(CC3CCCCC3)cc(-c3ccco3)c2c1N

Standard InChI:  InChI=1S/C19H21N3O2S/c20-16-15-13(14-7-4-8-24-14)10-12(9-11-5-2-1-3-6-11)22-19(15)25-17(16)18(21)23/h4,7-8,10-11H,1-3,5-6,9,20H2,(H2,21,23)

Standard InChI Key:  LXLJXSRRBGCWEF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    6.3268  -23.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3668  -23.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6732  -22.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9392  -22.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9031  -23.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5975  -24.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7589  -23.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7558  -23.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4688  -24.2748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4710  -22.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1846  -23.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1821  -23.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9724  -24.1253    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4635  -23.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9766  -22.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2339  -21.9956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2885  -23.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6988  -24.1721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7032  -22.7431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4705  -21.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1325  -21.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8771  -20.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0520  -20.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7977  -21.3141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0400  -24.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
  1  2  1  0
  3  4  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  7  8  2  0
 15 16  1  0
 14 17  1  0
  8  9  1  0
 17 18  2  0
  9 12  2  0
 17 19  1  0
  4  5  1  0
 10 20  1  0
 20 21  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
  2  3  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
  5  6  1  0
  8 25  1  0
 25  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089298

   3-Amino-6-(cyclohexylmethyl)-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: 355.46

Molecular Weight (Monoisotopic): 355.1354

AlogP: 4.36

#Rotatable Bonds: 4

Polar Surface Area: 95.14

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.73

Np Likeness Score: -1.35

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