1-ethyl-3-(4-(2-(pyridin-3-yl)vinyl)-5-(1H-pyrrol-2-yl)thiazol-2-yl)urea

ID: ALA3736029

PubChem CID: 92045129

Max Phase: Preclinical

Molecular Formula: C17H17N5OS

Molecular Weight: 339.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)Nc1nc(/C=C/c2cccnc2)c(-c2ccc[nH]2)s1

Standard InChI:  InChI=1S/C17H17N5OS/c1-2-19-16(23)22-17-21-14(8-7-12-5-3-9-18-11-12)15(24-17)13-6-4-10-20-13/h3-11,20H,2H2,1H3,(H2,19,21,22,23)/b8-7+

Standard InChI Key:  KXSSNSOHTLLWNT-BQYQJAHWSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    5.2447   -3.1359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2484   -4.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0312   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7388   -4.0972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6192   -5.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1121   -5.1589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1292   -6.4080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9925   -6.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1862   -6.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9100   -6.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -6.0210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7951   -7.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812   -8.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -7.6949    0.0000 C   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 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
   -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
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 12  2  0
  5 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3736029

   1-Ethyl-3-{4-[(E)-2-(Pyridin-3-Yl)ethenyl]-5-(1h-Pyrrol-2-Yl)-1,3-Thiazol-2-Yl}urea

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: 339.42

Molecular Weight (Monoisotopic): 339.1154

AlogP: 3.85

#Rotatable Bonds: 5

Polar Surface Area: 82.70

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.85

CX Basic pKa: 4.86

CX LogP: 2.80

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -1.62

References

1. Zhang J, Yang Q, Cross JB, Romero JA, Poutsiaka KM, Epie F, Bevan D, Wang B, Zhang Y, Chavan A, Zhang X, Moy T, Daniel A, Nguyen K, Chamberlain B, Carter N, Shotwell J, Silverman J, Metcalf CA, Ryan D, Lippa B, Dolle RE..  (2015)  Discovery of Azaindole Ureas as a Novel Class of Bacterial Gyrase B Inhibitors.,  58  (21): [PMID:26460684] [10.1021/acs.jmedchem.5b00961]

Source

Source(1):

• Scientific Literature