3-amino-4-(5-ethylfuran-2-yl)-5,6,7,8,9,10-hexahydrocycloocta[b]thieno[3,2-e]pyridine-2-carboxamide

ID: ALA1091075

PubChem CID: 46884245

Max Phase: Preclinical

Molecular Formula: C20H23N3O2S

Molecular Weight: 369.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(-c2c3c(nc4sc(C(N)=O)c(N)c24)CCCCCC3)o1

Standard InChI:  InChI=1S/C20H23N3O2S/c1-2-11-9-10-14(25-11)15-12-7-5-3-4-6-8-13(12)23-20-16(15)17(21)18(26-20)19(22)24/h9-10H,2-8,21H2,1H3,(H2,22,24)

Standard InChI Key:  WFLFCWLGESAVJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.6964   -2.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1117   -1.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1116   -3.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -3.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2842   -1.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036   -2.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067   -3.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9937   -3.5081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915   -1.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779   -2.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2804   -3.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099   -3.3587    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0010   -2.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -2.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714   -1.2289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260   -2.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2363   -3.4054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2407   -1.9765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920   -1.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3300   -0.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5854    0.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105    0.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6648   -0.5475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959    0.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5608    1.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  3  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  1  2  1  0
 15 16  1  0
  7  8  2  0
 14 17  1  0
  2  3  1  0
 17 18  2  0
  8  9  1  0
 17 19  1  0
  9 12  2  0
 10 20  1  0
 20 21  2  0
  1  4  1  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
  4  5  1  0
 23 25  1  0
  5  8  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091075

   6-Amino-8-(5-ethylfuran-2-yl)-4-thia-2-azatricyclo[7.6.0.03,7]pentadeca-1(9),2,5,7-tetraene-5-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: 369.49

Molecular Weight (Monoisotopic): 369.1511

AlogP: 4.46

#Rotatable Bonds: 3

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: 4.45

CX LogD: 4.45

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.37

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