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

ID: ALA1089019

PubChem CID: 46884209

Max Phase: Preclinical

Molecular Formula: C19H18F3N3O2S

Molecular Weight: 409.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1sc2nc3c(c(-c4ccc(C(F)(F)F)o4)c2c1N)CCCCCC3

Standard InChI:  InChI=1S/C19H18F3N3O2S/c20-19(21,22)12-8-7-11(27-12)13-9-5-3-1-2-4-6-10(9)25-18-14(13)15(23)16(28-18)17(24)26/h7-8H,1-6,23H2,(H2,24,26)

Standard InChI Key:  VHLDQURHHUWKSX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.8910  -23.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8911  -22.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4758  -21.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4759  -23.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033  -23.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3033  -21.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8839  -22.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8808  -23.0732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5938  -23.4873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5960  -21.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3096  -22.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3071  -23.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0974  -23.3378    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.5885  -22.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1016  -21.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3589  -21.2081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4135  -22.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8238  -23.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8282  -21.9556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5955  -21.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2575  -20.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0021  -19.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1770  -19.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9227  -20.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6916  -19.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0267  -18.3208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8712  -19.1615    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9708  -18.6583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
  7  6  1  0
 25 27  1  0
  6  3  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089019

   6-Amino-8-[5-(trifluoromethyl)furan-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: 409.43

Molecular Weight (Monoisotopic): 409.1072

AlogP: 4.92

#Rotatable Bonds: 2

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: 4.52

CX LogD: 4.52

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -1.30

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