US8586620, 97

ID: ALA3645475

PubChem CID: 15951272

Max Phase: Preclinical

Molecular Formula: C19H22N4S

Molecular Weight: 338.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCC[C@@H]1Cc1c[nH]c2ccc(/N=C(\N)c3cccs3)cc12

Standard InChI:  InChI=1S/C19H22N4S/c1-23-8-2-4-15(23)10-13-12-21-17-7-6-14(11-16(13)17)22-19(20)18-5-3-9-24-18/h3,5-7,9,11-12,15,21H,2,4,8,10H2,1H3,(H2,20,22)/t15-/m1/s1

Standard InChI Key:  NXMUTZARWRLWNI-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  1  0  0  0  0  0999 V2000
   -2.3079   -6.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1079   -6.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2222   -7.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028   -7.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1979   -5.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -5.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    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
   -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
   -2.6003    1.4977    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
   -3.8969   -0.4545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5517    0.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5554    1.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8054    3.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3382    2.9741    0.0000 S   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  2  1  0
  6  7  1  1
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  8  1  0
 16 11  1  0
 14 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3645475

   N'-[3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indol-5-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: 338.48

Molecular Weight (Monoisotopic): 338.1565

AlogP: 3.90

#Rotatable Bonds: 4

Polar Surface Area: 57.41

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.65

CX LogP: 3.65

CX LogD: 1.22

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.56

Np Likeness Score: -0.93

References

1.  (2013)  Substituted indole compounds having NOS inhibitory activity, 

Source

Source(1):

• BindingDB Database