US8912224, 321

ID: ALA3661996

PubChem CID: 71292871

Max Phase: Preclinical

Molecular Formula: C22H22N2O3S

Molecular Weight: 394.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1cnc(Oc2ccc3c(c2)CCC(c2ccccc2)O3)s1

Standard InChI:  InChI=1S/C22H22N2O3S/c1-2-12-23-21(25)20-14-24-22(28-20)26-17-9-11-19-16(13-17)8-10-18(27-19)15-6-4-3-5-7-15/h3-7,9,11,13-14,18H,2,8,10,12H2,1H3,(H,23,25)

Standard InChI Key:  MZLAALXYKJSUIA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -3.6334   -8.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227   -7.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4309   -7.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5420   -6.3307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498   -6.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -7.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056   -3.8679    0.0000 N   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
    2.5973   -1.5031    0.0000 O   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
    0.0000    1.5000    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
   -2.5981    1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    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
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1968    1.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995    3.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7974    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7950    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4948    0.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -3.8595    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 15  1  0
 20 21  2  0
 21 12  1  0
 17 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 10 28  1  0
 28  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3661996

   2-[(2-phenyl-3,4-dihydro-2H-chromen-6-yl)oxy]-N-propyl-1,3-thiazole-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: 394.50

Molecular Weight (Monoisotopic): 394.1351

AlogP: 5.14

#Rotatable Bonds: 6

Polar Surface Area: 60.45

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.36

CX Basic pKa: ┄

CX LogP: 5.01

CX LogD: 5.01

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: -0.56

References

1.  (2014)  Substituted 2-(chroman-6-yloxy)-thiazoles and their use as pharmaceuticals, 

Source

Source(1):

• BindingDB Database