8-Oxo-2-(pyridin-2-ylmethoxy)-7-pyridin-3-ylmethyl-5-(3,4,5-trimethoxy-phenyl)-7,8-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester 2M HCl

ID: ALA539266

Cas Number: 324572-03-4

PubChem CID: 44314926

Max Phase: Preclinical

Molecular Formula: C31H29ClN4O7

Molecular Weight: 568.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ccccn3)nc2c(=O)n1Cc1cccnc1.Cl

Standard InChI:  InChI=1S/C31H28N4O7.ClH/c1-38-23-14-20(15-24(39-2)29(23)40-3)26-22-10-11-25(42-18-21-9-5-6-13-33-21)34-27(22)30(36)35(28(26)31(37)41-4)17-19-8-7-12-32-16-19;/h5-16H,17-18H2,1-4H3;1H

Standard InChI Key:  VMYRWJCEOPQNRD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -0.3958   -4.2292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -1.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -1.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -3.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -1.4875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1875   -3.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -5.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -3.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6042   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417   -0.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -1.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -2.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917    0.5958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -1.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5375   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -6.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1875   -3.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1875   -5.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -5.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -0.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -4.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -5.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4625    0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  2  0
  5  2  1  0
  6  5  1  0
  7  6  1  0
  8  4  1  0
  9  6  2  0
 10  3  1  0
 11 12  2  0
 12 15  1  0
 13 14  2  0
 14  8  1  0
 15  8  2  0
 16  2  1  0
 17  7  2  0
 18  9  1  0
 19  5  2  0
 20 26  1  0
 21 10  2  0
 22 32  1  0
 23 16  1  0
 24 18  1  0
 25 18  2  0
 26 31  1  0
 27 11  1  0
 28 10  1  0
 29 12  1  0
 30 13  1  0
 31 24  1  0
 32 23  2  0
 33 20  2  0
 34 41  1  0
 35 23  1  0
 36 26  2  0
 37 27  1  0
 38 28  1  0
 39 29  1  0
 40 30  1  0
 41 35  2  0
 42 43  2  0
 43 36  1  0
  7  4  1  0
 22 34  2  0
 25 17  1  0
 13 11  1  0
 33 42  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: 568.59

Molecular Weight (Monoisotopic): 568.1958

AlogP: 4.29

#Rotatable Bonds: 10

Polar Surface Area: 123.89

Molecular Species: NEUTRAL

HBA: 11

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 4.85

CX LogP: 3.21

CX LogD: 3.21

Aromatic Rings: 5

Heavy Atoms: 42

QED Weighted: 0.23

Np Likeness Score: -0.92

References

1. Ukita T, Nakamura Y, Kubo A, Yamamoto Y, Moritani Y, Saruta K, Higashijima T, Kotera J, Fujishige K, Takagi M, Kikkawa K, Omori K..  (2003)  1,7- and 2,7-naphthyridine derivatives as potent and highly specific PDE5 inhibitors.,  13  (14): [PMID:12824030] [10.1016/s0960-894x(03)00440-2]

Source

Source(1):

• Scientific Literature