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

ID: ALA1090391

PubChem CID: 46884207

Max Phase: Preclinical

Molecular Formula: C22H25N3OS

Molecular Weight: 379.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1sc2nc3c(c(CCc4ccccc4)c2c1N)CCCCCC3

Standard InChI:  InChI=1S/C22H25N3OS/c23-19-18-16(13-12-14-8-4-3-5-9-14)15-10-6-1-2-7-11-17(15)25-22(18)27-20(19)21(24)26/h3-5,8-9H,1-2,6-7,10-13,23H2,(H2,24,26)

Standard InChI Key:  CGYOGQIVPPSZQL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   15.9160  -15.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9161  -14.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5008  -13.6203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5009  -15.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3283  -15.6132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3283  -13.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9089  -14.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9058  -15.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6188  -15.4456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6210  -13.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3346  -14.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3321  -15.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1224  -15.2962    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.6135  -14.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1266  -13.9503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3839  -13.1664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4385  -14.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8488  -15.3429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8532  -13.9140    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6205  -12.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3348  -12.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3343  -11.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0493  -11.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0492  -10.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3339  -10.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6173  -10.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6210  -11.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1  4  1  0
 20 21  1  0
 11 10  2  0
 21 22  1  0
 10  7  1  0
 22 23  2  0
 11 12  1  0
 23 24  1  0
  4  5  1  0
 24 25  2  0
  5  8  1  0
 25 26  1  0
  7  6  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090391

   6-Amino-8-(2-phenylethyl)-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: 379.53

Molecular Weight (Monoisotopic): 379.1718

AlogP: 4.42

#Rotatable Bonds: 4

Polar Surface Area: 82.00

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.62

CX LogP: 5.55

CX LogD: 5.55

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.97

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