2-(2-Hydroxycarbamoylmethyl-3-oxo-2,3-dihydro-benzo[1,4]thiazin-4-yl)-propionamide

ID: ALA286238

PubChem CID: 11162652

Max Phase: Preclinical

Molecular Formula: C13H15N3O4S

Molecular Weight: 309.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C(N)=O)N1C(=O)C(CC(=O)NO)Sc2ccccc21

Standard InChI:  InChI=1S/C13H15N3O4S/c1-7(12(14)18)16-8-4-2-3-5-9(8)21-10(13(16)19)6-11(17)15-20/h2-5,7,10,20H,6H2,1H3,(H2,14,18)(H,15,17)

Standard InChI Key:  YXBYJUJBZWKXTN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -0.7958   -0.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000    1.3000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5083    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5125    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292    1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375   -0.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6250   -1.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500    0.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.3083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000   -2.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750    0.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2333   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2333    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208   -1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9458    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9458    0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  7  1  0
  5  1  1  0
  6  1  1  0
  7  5  1  0
  8  3  1  0
  9  6  1  0
 10  8  1  0
 11  2  2  0
 12  9  2  0
 13 10  2  0
 14 10  1  0
 15  9  1  0
 16 14  1  0
 17  5  2  0
 18  7  2  0
 19  6  1  0
 20 17  1  0
 21 20  2  0
  4  3  1  0
 21 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA286238

   2-(2-Hydroxycarbamoylmethyl-3-oxo-2,3-dihydro-benzo[1,4]thiazin-4-yl)-propionamide

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: 309.35

Molecular Weight (Monoisotopic): 309.0783

AlogP: 0.26

#Rotatable Bonds: 4

Polar Surface Area: 112.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.89

CX Basic pKa: ┄

CX LogP: -0.55

CX LogD: -0.56

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: -0.97

References

1. Molteni V, He X, Nabakka J, Yang K, Kreusch A, Gordon P, Bursulaya B, Warner I, Shin T, Biorac T, Ryder NS, Goldberg R, Doughty J, He Y..  (2004)  Identification of novel potent bicyclic peptide deformylase inhibitors.,  14  (6): [PMID:15006385] [10.1016/j.bmcl.2004.01.014]

Source

Source(1):

• Scientific Literature