[4-Amino-2-(3-methoxyphenylamino)-thiazol-5-yl]-phenylmethanone

ID: ALA553481

PubChem CID: 44250179

Max Phase: Preclinical

Molecular Formula: C17H15N3O2S

Molecular Weight: 325.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(Nc2nc(N)c(C(=O)c3ccccc3)s2)c1

Standard InChI:  InChI=1S/C17H15N3O2S/c1-22-13-9-5-8-12(10-13)19-17-20-16(18)15(23-17)14(21)11-6-3-2-4-7-11/h2-10H,18H2,1H3,(H,19,20)

Standard InChI Key:  BMACDARQSMTWPD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.6520   -0.5710    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3970   -1.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5720   -1.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171   -0.5710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9845   -0.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8819   -2.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7024   -1.9368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5464   -2.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9845    0.7390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    1.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2700    1.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    2.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411    1.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411    1.1515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    0.7390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0313   -3.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957   -4.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8753   -4.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3903   -3.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7259   -2.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0871   -2.0230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556    3.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8411    3.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
 11 12  1  0
  2  6  1  0
 12 13  2  0
 13 14  1  0
  6  7  2  0
 14 15  2  0
 15 10  1  0
  2  3  2  0
  8 16  2  0
  6  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  2  0
  5  9  1  0
 18 19  1  0
  4  5  2  0
 19 20  2  0
 20  8  1  0
  9 10  1  0
  3 21  1  0
  5  1  1  0
 12 22  1  0
 10 11  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA553481

   [4-Amino-2-(3-methoxyanilino)-1,3-thiazol-5-yl]-phenylmethanone

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: 325.39

Molecular Weight (Monoisotopic): 325.0885

AlogP: 3.71

#Rotatable Bonds: 5

Polar Surface Area: 77.24

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.14

CX Basic pKa: 1.40

CX LogP: 4.61

CX LogD: 4.61

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -1.45

References

1. Romagnoli R, Baraldi PG, Carrion MD, Cruz-Lopez O, Cara CL, Basso G, Viola G, Khedr M, Balzarini J, Mahboobi S, Sellmer A, Brancale A, Hamel E..  (2009)  2-Arylamino-4-amino-5-aroylthiazoles. "One-pot" synthesis and biological evaluation of a new class of inhibitors of tubulin polymerization.,  52  (17): [PMID:19663386] [10.1021/jm9001692]

Source

Source(1):

• Scientific Literature