(S)-1-{2-[(2-Pyridin-3-yl-thiazole-4-carbonyl)-amino]-acryloyl}-pyrrolidine-2-carboxylic acid methyl ester

ID: ALA191995

PubChem CID: 44400851

Max Phase: Preclinical

Molecular Formula: C18H18N4O4S

Molecular Weight: 386.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(NC(=O)c1csc(-c2cccnc2)n1)C(=O)N1CCC[C@H]1C(=O)OC

Standard InChI:  InChI=1S/C18H18N4O4S/c1-11(17(24)22-8-4-6-14(22)18(25)26-2)20-15(23)13-10-27-16(21-13)12-5-3-7-19-9-12/h3,5,7,9-10,14H,1,4,6,8H2,2H3,(H,20,23)/t14-/m0/s1

Standard InChI Key:  XZQNOIQADWZTPK-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  1  0  0  0  0  0999 V2000
   10.1417   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3875    0.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7375    0.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0167   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8292   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8625    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3000    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -1.0500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5792   -0.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4042    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0542   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -0.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1917    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0167   -0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8625    1.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3000    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8125    1.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0750    0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3417   -0.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1625    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792    0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3292    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1167   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625    0.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  7  1  0
  5  2  2  0
  6  1  1  0
  7  9  1  0
  8 11  1  0
  9  6  1  0
 10  3  1  0
 11  1  2  0
 12  5  1  0
 10 13  1  1
 14  4  2  0
 15  6  2  0
 16  7  2  0
 17 13  2  0
 18 20  2  0
 19  3  1  0
 20 12  1  0
 21 13  1  0
 22 10  1  0
 23 12  2  0
 24 19  1  0
 25 27  2  0
 26 21  1  0
 27 23  1  0
  8  5  1  0
 25 18  1  0
 24 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA191995

   methyl (2S)-1-[2-[(2-pyridin-3-yl-1,3-thiazole-4-carbonyl)amino]prop-2-enoyl]pyrrolidine-2-carboxylate

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: 386.43

Molecular Weight (Monoisotopic): 386.1049

AlogP: 1.61

#Rotatable Bonds: 5

Polar Surface Area: 101.49

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.18

CX Basic pKa: 3.99

CX LogP: 0.78

CX LogD: 0.78

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: -1.36

References

1. Ayida BK, Simonsen KB, Vourloumis D, Hermann T..  (2005)  Synthesis of dehydroalanine fragments as thiostrepton side chain mimetics.,  15  (10): [PMID:15863296] [10.1016/j.bmcl.2005.03.084]

Source

Source(1):

• Scientific Literature