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

ID: ALA1202833

PubChem CID: 49860443

Max Phase: Preclinical

Molecular Formula: C32H32ClN5O6

Molecular Weight: 581.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(NCc3ccccn3)nc2c(=O)n1Cc1ccnc(C)c1.Cl

Standard InChI:  InChI=1S/C32H31N5O6.ClH/c1-19-14-20(11-13-33-19)18-37-29(32(39)43-5)27(21-15-24(40-2)30(42-4)25(16-21)41-3)23-9-10-26(36-28(23)31(37)38)35-17-22-8-6-7-12-34-22;/h6-16H,17-18H2,1-5H3,(H,35,36);1H

Standard InChI Key:  BMPBVARHWQIZQY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 44 47  0  0  0  0  0  0  0  0999 V2000
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   -3.9122    1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501    0.8944    0.0000 O   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
   -1.2919    2.9980    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
    0.0151    5.2437    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
    2.3553    5.3817    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
   -1.2791    7.4991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3171    8.1012    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
   -3.8816    6.0051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.5017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -3.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1872   -3.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1872   -5.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -6.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7853   -5.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7853   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -3.0057    0.0000 N   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
    0.0000   -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
   -1.2928   -2.6973    0.0000 O   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
   -3.9122   -1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9158   -2.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2152   -3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2159   -5.2469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9172   -5.9975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -5.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788   -5.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171   -3.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19  8  1  0
  7 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 23 32  1  0
 32 33  2  0
 33 20  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36  6  1  0
 36 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  1  0
 42 44  2  0
 44 38  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: 581.63

Molecular Weight (Monoisotopic): 581.2274

AlogP: 4.63

#Rotatable Bonds: 10

Polar Surface Area: 126.69

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 5.72

CX LogP: 2.98

CX LogD: 2.97

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.23

Np Likeness Score: -0.88

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