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

ID: ALA553729

PubChem CID: 45260807

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)n1-c1ccc(N)cc1.Cl

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

Standard InChI Key:  XOIYPORDLDIDPY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 43 46  0  0  0  0  0  0  0  0999 V2000
   11.5923   -2.2456    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2919   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091   -1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2813   -5.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5829   -5.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151   -5.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7933    0.7419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494   -0.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942    1.4964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097    3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071    0.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4942    1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729   -7.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9067   -3.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5078    3.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191   -5.9869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8816   -6.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929    0.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5474    3.6002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2093    3.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067    1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0923    1.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4943    2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -8.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9221   -5.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553   -5.3817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9447   -3.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0923    2.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7933    3.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  4  1  0
  3  5  2  0
  4  6  1  0
  5  7  1  0
  6  7  1  0
  5  8  1  0
  6  9  2  0
  3 10  1  0
 11 12  2  0
 11 13  1  0
  2 14  1  0
  8 15  1  0
 13 15  2  0
  8 16  2  0
 12 16  1  0
  7 17  2  0
  4 18  2  0
  9 19  1  0
 10 21  2  0
 19 22  1  0
 14 23  2  0
 14 24  1  0
 17 25  1  0
 19 25  2  0
 20 26  1  0
 11 27  1  0
 10 28  1  0
 13 30  1  0
 12 31  1  0
 22 32  1  0
 26 32  1  0
 29 33  1  0
 23 34  1  0
 29 34  2  0
 24 35  2  0
 29 35  1  0
 20 36  2  0
 26 37  2  0
 27 38  1  0
 31 39  1  0
 30 40  1  0
 28 41  1  0
 36 42  1  0
 37 43  1  0
 42 43  2  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: 4.42

#Rotatable Bonds: 9

Polar Surface Area: 137.02

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 3.87

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 5

Heavy Atoms: 42

QED Weighted: 0.20

Np Likeness Score: -0.81

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