7-(3-(Aminomethyl)-4-((5-methylisoxazol-3-yl)methoxy)phenyl)-4-methylquinolin-2-amine

ID: ALA4468534

PubChem CID: 155533249

Max Phase: Preclinical

Molecular Formula: C22H22N4O2

Molecular Weight: 374.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(COc2ccc(-c3ccc4c(C)cc(N)nc4c3)cc2CN)no1

Standard InChI:  InChI=1S/C22H22N4O2/c1-13-7-22(24)25-20-10-16(3-5-19(13)20)15-4-6-21(17(9-15)11-23)27-12-18-8-14(2)28-26-18/h3-10H,11-12,23H2,1-2H3,(H2,24,25)

Standard InChI Key:  HOQPHJZRSVCLCE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.7469  -21.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4591  -22.3434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4573  -20.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1701  -21.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1708  -21.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8835  -22.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5959  -21.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5911  -21.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8779  -20.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0348  -22.3424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4549  -19.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3016  -22.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3042  -23.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0038  -21.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7118  -22.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7224  -23.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0141  -23.5492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4144  -21.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1271  -22.2930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4340  -23.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4418  -24.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1534  -24.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2507  -25.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0516  -25.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4535  -25.0143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9008  -24.4123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3912  -26.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
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  2 11  1  0
  4 12  1  0
 13 14  2  0
 14 18  1  0
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  8 13  1  0
 15 16  2  0
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 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 23  2  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4468534

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 374.44

Molecular Weight (Monoisotopic): 374.1743

AlogP: 4.13

#Rotatable Bonds: 5

Polar Surface Area: 100.19

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.69

CX LogP: 3.40

CX LogD: 2.00

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -1.02

References

1. Cinelli MA, Reidl CT, Li H, Chreifi G, Poulos TL, Silverman RB..  (2020)  First Contact: 7-Phenyl-2-Aminoquinolines, Potent and Selective Neuronal Nitric Oxide Synthase Inhibitors That Target an Isoform-Specific Aspartate.,  63  (9): [PMID:32302123] [10.1021/acs.jmedchem.9b01573]

Source

Source(1):

• Scientific Literature