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

ID: ALA542410

PubChem CID: 44314916

Max Phase: Preclinical

Molecular Formula: C31H30ClN5O7

Molecular Weight: 583.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1c(-c2cc(OC)c(OC)c(OC)c2)c2ccc(OCc3ncccn3)nc2c(=O)n1Cc1ccnc(C)c1.Cl

Standard InChI:  InChI=1S/C31H29N5O7.ClH/c1-18-13-19(9-12-32-18)16-36-28(31(38)42-5)26(20-14-22(39-2)29(41-4)23(15-20)40-3)21-7-8-25(35-27(21)30(36)37)43-17-24-33-10-6-11-34-24;/h6-15H,16-17H2,1-5H3;1H

Standard InChI Key:  LFKKHEZGIPBVJG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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
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    7.7933    0.7419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4943    2.9919    0.0000 N   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
   -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
    3.8942    1.4964    0.0000 O   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
    5.1929    0.7441    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
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   -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
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    7.7933    3.7419    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
   -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
  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
 20 21  2  0
 20 22  1  0
 10 24  2  0
 16 25  1  0
 18 26  1  0
 17 27  1  0
 18 27  2  0
 23 28  2  0
 20 29  1  0
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 11 30  1  0
 25 31  2  0
 28 31  1  0
 10 32  1  0
 12 33  1  0
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 25 39  1  0
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 34 43  1  0
 32 44  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: 583.60

Molecular Weight (Monoisotopic): 583.2067

AlogP: 4.00

#Rotatable Bonds: 10

Polar Surface Area: 136.78

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 5.72

CX LogP: 3.29

CX LogD: 3.28

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.22

Np Likeness Score: -0.73

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