US8912224, 342

ID: ALA3662017

PubChem CID: 71509625

Max Phase: Preclinical

Molecular Formula: C22H21FN2O4S

Molecular Weight: 428.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(F)cc1C1CCc2cc(Oc3ncc(C(=O)NCCO)s3)ccc2O1

Standard InChI:  InChI=1S/C22H21FN2O4S/c1-13-2-4-15(23)11-17(13)19-6-3-14-10-16(5-7-18(14)29-19)28-22-25-12-20(30-22)21(27)24-8-9-26/h2,4-5,7,10-12,19,26H,3,6,8-9H2,1H3,(H,24,27)

Standard InChI Key:  ASOCGOYSMCISKT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.9010    0.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1945   -3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8924   -4.9525    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    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
    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 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
   -5.1984    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4971    0.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8506    1.3617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8505    0.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0959   -1.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6298   -0.7359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6977   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8905   -2.5567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8096   -3.6348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4124   -5.0092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5243   -6.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0062   -7.3180    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
   -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 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  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 14 27  2  0
 27 28  1  0
 28 29  2  0
 29 12  1  0
 29 30  1  0
 30  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3662017

   2-[[2-(5-fluoro-2-methylphenyl)-3,4-dihydro-2H-chromen-6-yl]oxy]-N-(2-hydroxyethyl)-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: 428.49

Molecular Weight (Monoisotopic): 428.1206

AlogP: 4.17

#Rotatable Bonds: 6

Polar Surface Area: 80.68

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.33

CX Basic pKa: ┄

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.62

Np Likeness Score: -0.74

References

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

Source

Source(1):

• BindingDB Database