2-[4-(2-Cyclohexyl-ethyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl]-N-hydroxy-acetamide

ID: ALA35042

PubChem CID: 44283282

Max Phase: Preclinical

Molecular Formula: C18H24N2O3S

Molecular Weight: 348.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CC1Sc2ccccc2N(CCC2CCCCC2)C1=O)NO

Standard InChI:  InChI=1S/C18H24N2O3S/c21-17(19-23)12-16-18(22)20(11-10-13-6-2-1-3-7-13)14-8-4-5-9-15(14)24-16/h4-5,8-9,13,16,23H,1-3,6-7,10-12H2,(H,19,21)

Standard InChI Key:  AMFGMQJPZJSMRY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -1.8333   -0.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333    1.0458    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458    0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3125    0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -0.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -0.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0250    1.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417    0.6458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    1.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4208   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9750   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9750    0.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  6  1  0
  5  1  1  0
  6  5  1  0
  7  3  1  0
  8  1  1  0
  9  7  1  0
 10  2  2  0
 11  9  2  0
 12  9  1  0
 13  8  1  0
 14 12  1  0
 15  5  2  0
 16  6  2  0
 17 13  1  0
 18 17  1  0
 19 17  1  0
 20 15  1  0
 21 20  2  0
 22 19  1  0
 23 18  1  0
 24 22  1  0
  4  3  1  0
 21 16  1  0
 24 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA35042

   2-[4-(2-Cyclohexyl-ethyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-2-yl]-N-hydroxy-acetamide

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: 348.47

Molecular Weight (Monoisotopic): 348.1508

AlogP: 3.36

#Rotatable Bonds: 5

Polar Surface Area: 69.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.89

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 2.68

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -0.93

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