US8618286, 3

ID: ALA3675231

PubChem CID: 44599933

Max Phase: Preclinical

Molecular Formula: C19H22N4O2S

Molecular Weight: 370.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N/C(=N\c1ccc2c(c1)OCC(=O)N2CCN1CCCC1)c1cccs1

Standard InChI:  InChI=1S/C19H22N4O2S/c20-19(17-4-3-11-26-17)21-14-5-6-15-16(12-14)25-13-18(24)23(15)10-9-22-7-1-2-8-22/h3-6,11-12H,1-2,7-10,13H2,(H2,20,21)

Standard InChI Key:  LFKLDLHIJLFFAI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    1.5548   -3.6021    0.0000 N   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 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
    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
   -2.5981    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9020    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9051    5.2502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1186    6.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6551    7.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1551    7.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6916    6.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9364    1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    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
    0.0000   -1.5000    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
    4.0312   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4984   -5.5497    0.0000 C   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
    5.2447   -3.1359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  8 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20  7  1  0
 20 21  2  0
 21  4  1  0
  2 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3675231

   N-(3-Oxo-4-(2-(pyrrolidin-1-yl)ethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-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: 370.48

Molecular Weight (Monoisotopic): 370.1463

AlogP: 2.61

#Rotatable Bonds: 5

Polar Surface Area: 71.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.97

CX LogP: 1.93

CX LogD: 1.18

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.65

Np Likeness Score: -1.83

References

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

Source

Source(1):

• BindingDB Database