(R)-4-methoxy-2-(3-(methylamino)-1-phenylpropoxy)benzonitrile oxalate

ID: ALA1762476

PubChem CID: 54583931

Max Phase: Preclinical

Molecular Formula: C20H22N2O6

Molecular Weight: 296.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCC[C@@H](Oc1cc(OC)ccc1C#N)c1ccccc1.O=C(O)C(=O)O

Standard InChI:  InChI=1S/C18H20N2O2.C2H2O4/c1-20-11-10-17(14-6-4-3-5-7-14)22-18-12-16(21-2)9-8-15(18)13-19;3-1(4)2(5)6/h3-9,12,17,20H,10-11H2,1-2H3;(H,3,4)(H,5,6)/t17-;/m1./s1

Standard InChI Key:  FCJZJQBLFVEPPT-UNTBIKODSA-N

Molfile:  

     RDKit          2D

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   11.7250  -14.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4395  -14.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1539  -14.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4395  -13.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0105  -14.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7250  -15.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2486  -15.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2474  -15.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9622  -16.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6787  -15.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6758  -15.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9604  -14.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3938  -16.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1076  -15.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8227  -16.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5365  -15.9349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1048  -15.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8203  -14.7041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8193  -13.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1037  -13.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3875  -13.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3919  -14.7086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9620  -17.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9580  -13.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2517  -16.3462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9648  -17.9986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2423  -13.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2530  -17.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  2  0
 19 20  2  0
  8  9  1  0
 20 21  1  0
 10 13  1  0
 21 22  2  0
 22 17  1  0
 14 17  1  1
  9 23  1  0
 13 14  1  0
 12 24  1  0
  9 10  2  0
 16 25  1  0
 14 15  1  0
 23 26  3  0
  7  8  2  0
 24 27  1  0
 15 16  1  0
 25 28  1  0
 10 11  1  0
 17 18  2  0
 11 12  2  0
 18 19  1  0
 12  7  1  0
M  END

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: 296.37

Molecular Weight (Monoisotopic): 296.1525

AlogP: 3.30

#Rotatable Bonds: 7

Polar Surface Area: 54.28

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.80

CX LogP: 2.99

CX LogD: 0.65

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.85

Np Likeness Score: -0.34

References

1. Cheshire DR, Åberg A, Andersson GM, Andrews G, Beaton HG, Birkinshaw TN, Boughton-Smith N, Connolly S, Cook TR, Cooper A, Cooper SL, Cox D, Dixon J, Gensmantel N, Hamley PJ, Harrison R, Hartopp P, Käck H, Leeson PD, Luker T, Mete A, Millichip I, Nicholls DJ, Pimm AD, St-Gallay SA, Wallace AV..  (2011)  The discovery of novel, potent and highly selective inhibitors of inducible nitric oxide synthase (iNOS).,  21  (8): [PMID:21398123] [10.1016/j.bmcl.2011.02.061]

Source

Source(1):

• Scientific Literature