US8618286, 9

ID: ALA3675237

PubChem CID: 44600087

Max Phase: Preclinical

Molecular Formula: C17H22N4OS

Molecular Weight: 330.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCN1CCOc2ccc(/N=C(\N)c3cccs3)cc21

Standard InChI:  InChI=1S/C17H22N4OS/c1-20(2)7-8-21-9-10-22-15-6-5-13(12-14(15)21)19-17(18)16-4-3-11-23-16/h3-6,11-12H,7-10H2,1-2H3,(H2,18,19)

Standard InChI Key:  WKVNASUFBKWTKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    6.2387   -0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -1.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2024   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    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
    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 O   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
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0000    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
   -1.2959   -5.2508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -5.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431   -5.3976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080   -7.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2215   -8.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7580   -9.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7420   -9.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055   -8.3601    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  6  1  0
 15 10  1  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3675237

   N-(4-(2-(dimethylamino)ethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)thiophene-2-carboximidamide

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: 330.46

Molecular Weight (Monoisotopic): 330.1514

AlogP: 2.55

#Rotatable Bonds: 5

Polar Surface Area: 54.09

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.92

CX LogP: 2.65

CX LogD: 0.39

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -1.91

References

1.  (2013)  Benzoxazines, benzothiazines, and related compounds having NOS inhibitory activity, 

Source

Source(1):

• BindingDB Database