US8618286, 17

ID: ALA3675245

PubChem CID: 44600245

Max Phase: Preclinical

Molecular Formula: C18H22N4O2S2

Molecular Weight: 390.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CCN1CCSc2cc(/N=C(\N)c3cccs3)ccc21)CC(=O)O

Standard InChI:  InChI=1S/C18H22N4O2S2/c1-21(12-17(23)24)6-7-22-8-10-26-16-11-13(4-5-14(16)22)20-18(19)15-3-2-9-25-15/h2-5,9,11H,6-8,10,12H2,1H3,(H2,19,20)(H,23,24)

Standard InChI Key:  GBISUSYSGDLKKW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.2024   -2.6932    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
    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 S   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
   -3.8963   -3.7531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8941   -5.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8539   -5.8521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1923   -6.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3302   -7.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7974   -7.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5474   -6.5007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5437   -5.3860    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8003   -1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8387   -0.8872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8024   -2.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  5  1  0
 14  9  1  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
  2 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3675245

   2-[2-[7-[[Amino(thiophen-2-yl)methylidene]amino]-2,3-dihydro-1,4-benzothiazin-4-yl]ethyl-methylamino]acetic acid

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: 390.53

Molecular Weight (Monoisotopic): 390.1184

AlogP: 2.71

#Rotatable Bonds: 7

Polar Surface Area: 82.16

Molecular Species: ZWITTERION

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.35

CX Basic pKa: 9.59

CX LogP: 0.72

CX LogD: -0.40

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: -1.79

References

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

Source

Source(1):

• BindingDB Database