US8785638, 188

ID: ALA3671014

PubChem CID: 49806458

Max Phase: Preclinical

Molecular Formula: C24H27NO3S2

Molecular Weight: 441.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2sc3c(c2c(Sc2ccccc2)c1C(OC(C)(C)C)C(=O)O)CCCC3

Standard InChI:  InChI=1S/C24H27NO3S2/c1-14-18(20(23(26)27)28-24(2,3)4)21(29-15-10-6-5-7-11-15)19-16-12-8-9-13-17(16)30-22(19)25-14/h5-7,10-11,20H,8-9,12-13H2,1-4H3,(H,26,27)

Standard InChI Key:  KWAZIOPNWPVELK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3115    2.9665    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8032    3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838    4.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1756    4.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7857    2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040    1.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4133    1.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8863   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3471   -5.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688   -5.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3089   -6.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938   -3.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900   -4.9562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -3.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  6  2  0
 11 12  1  0
 12  4  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 13 21  2  0
 21  2  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
 22 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3671014

   tert-Butoxy[2-methyl-4-(phenylsulfanyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]acetic acid

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: 441.62

Molecular Weight (Monoisotopic): 441.1432

AlogP: 6.58

#Rotatable Bonds: 5

Polar Surface Area: 59.42

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.38

CX Basic pKa: 2.26

CX LogP: 6.52

CX LogD: 3.62

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.48

Np Likeness Score: -1.20

References

1.  (2014)  Thieno [2, 3-B] pyridine derivatives as viral replication inhibitors, 

Source

Source(1):

• BindingDB Database