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

ID: ALA539357

PubChem CID: 45266037

Max Phase: Preclinical

Molecular Formula: C33H33ClN4O7

Molecular Weight: 596.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCCc3ccccn3)nc2c(=O)n1Cc1ccnc(C)c1.Cl

Standard InChI:  InChI=1S/C33H32N4O7.ClH/c1-20-16-21(11-14-34-20)19-37-30(33(39)43-5)28(22-17-25(40-2)31(42-4)26(18-22)41-3)24-9-10-27(36-29(24)32(37)38)44-15-12-23-8-6-7-13-35-23;/h6-11,13-14,16-18H,12,15,19H2,1-5H3;1H

Standard InChI Key:  UFWBSYCNSBCHQV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 45 48  0  0  0  0  0  0  0  0999 V2000
   12.8910   -1.1152    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
    0.0099   -3.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5882   -3.7528    0.0000 C   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
    1.2964   -1.4973    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
   -1.2928    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8958    6.0028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0945    1.4850    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
   -3.9067    3.0027    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
   -5.1976    5.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7928    0.7396    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
   -5.2030    3.7575    0.0000 C   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
   -3.8816   -6.0051    0.0000 O   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
    3.8942    1.4964    0.0000 O   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
   -2.5995    5.2481    0.0000 C   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
   10.3910    0.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050    3.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2346    5.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7877   -0.7605    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
    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
   -4.9221   -5.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3858   -0.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0842   -1.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  2  5  1  0
  5  6  1  0
  4  7  1  0
  6  7  1  0
  4  8  1  0
  6  9  2  0
  3 10  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 13 14  2  0
  8 15  2  0
 12 15  1  0
  2 16  1  0
  7 17  2  0
  9 18  1  0
  5 19  2  0
 10 22  2  0
 16 23  1  0
 17 24  1  0
 18 24  2  0
 20 25  2  0
 21 26  1  0
 11 27  1  0
 23 28  2  0
 25 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 18 32  1  0
 26 33  1  0
 20 34  1  0
 32 35  1  0
 33 35  1  0
 21 36  2  0
 23 37  1  0
 34 37  2  0
 25 38  1  0
 26 39  2  0
 27 40  1  0
 31 41  1  0
 29 42  1  0
 30 43  1  0
 36 44  1  0
 39 45  1  0
 44 45  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: 596.64

Molecular Weight (Monoisotopic): 596.2271

AlogP: 4.64

#Rotatable Bonds: 11

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: 5.85

CX LogP: 3.58

CX LogD: 3.57

Aromatic Rings: 5

Heavy Atoms: 44

QED Weighted: 0.20

Np Likeness Score: -0.79

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