Methyl (4R)-2-(Chloromethyl)-5-cyano-6-methyl-4-quinolin-4-yl-1,4-dihydropyridine-3-carboxylate

ID: ALA1094798

Max Phase: Preclinical

Molecular Formula: C19H16ClN3O2

Molecular Weight: 353.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(CCl)NC(C)=C(C#N)[C@H]1c1ccnc2ccccc12

Standard InChI:  InChI=1S/C19H16ClN3O2/c1-11-14(10-21)17(18(19(24)25-2)16(9-20)23-11)13-7-8-22-15-6-4-3-5-12(13)15/h3-8,17,23H,9H2,1-2H3/t17-/m1/s1

Standard InChI Key:  FLUAOTJNABTFRM-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

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    4.2111  -22.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2099  -23.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9247  -24.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229  -22.5580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9251  -25.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2087  -25.4421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2065  -26.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9190  -26.6801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6354  -26.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6393  -25.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904  -26.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3484  -26.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3543  -25.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4953  -25.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975  -24.2028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797  -25.4384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0664  -25.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0667  -24.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6383  -22.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391  -23.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3544  -24.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0694  -23.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0646  -22.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3487  -22.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7776  -26.2578    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  9 12  1  0
  2  3  1  0
 10 13  1  0
  3 20  2  0
  6 14  1  0
  1  2  2  0
 14 15  2  0
 19  4  2  0
 14 16  1  0
  4  1  1  0
 16 17  1  0
  5 10  1  0
 13 18  3  0
  6  7  2  0
  7  8  1  0
 19 20  1  0
  8  9  1  0
 20 21  1  0
  9 10  2  0
 21 22  2  0
  5  3  1  6
 22 23  1  0
  5  6  1  0
 23 24  2  0
 24 19  1  0
  7 11  1  0
 11 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094798

   ---

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: 353.81

Molecular Weight (Monoisotopic): 353.0931

AlogP: 3.39

#Rotatable Bonds: 3

Polar Surface Area: 75.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.41

CX LogP: 2.19

CX LogD: 2.19

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.68

Np Likeness Score: -0.96

References

1. Arhancet GB, Woodard SS, Dietz JD, Garland DJ, Wagner GM, Iyanar K, Collins JT, Blinn JR, Numann RE, Hu X, Huang HC..  (2010)  Stereochemical requirements for the mineralocorticoid receptor antagonist activity of dihydropyridines.,  53  (10): [PMID:20408553] [10.1021/jm1002827]

Source

Source(1):

• Scientific Literature