1-{3-[6-(1-Hydroxy-1-methyl-ethyl)-1-oxy-pyridin-3-yl]-phenyl}-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid cyclopropylamide

ID: ALA485620

PubChem CID: 10297996

Max Phase: Preclinical

Molecular Formula: C26H24N4O4

Molecular Weight: 456.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)c1ccc(-c2cccc(-n3cc(C(=O)NC4CC4)c(=O)c4cccnc43)c2)c[n+]1[O-]

Standard InChI:  InChI=1S/C26H24N4O4/c1-26(2,33)22-11-8-17(14-30(22)34)16-5-3-6-19(13-16)29-15-21(25(32)28-18-9-10-18)23(31)20-7-4-12-27-24(20)29/h3-8,11-15,18,33H,9-10H2,1-2H3,(H,28,32)

Standard InChI Key:  GVABMKVKGRIEOY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -1.0630   -3.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485   -3.4654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3485   -1.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -2.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -3.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804   -3.4654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7949   -3.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0804   -1.8154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0804   -0.9904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3660   -4.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -5.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9383   -5.9404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9383   -6.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2238   -7.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -6.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5094   -0.9904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2238   -0.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0488   -0.5779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363    0.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6528   -7.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3673   -7.5904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2403   -7.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0653   -6.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6528   -5.5279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  2  0
 17 12  1  0
  7 12  1  0
  5  4  2  0
  9 18  1  0
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  4  1  1  0
  9 10  1  0
 20 21  2  0
 10  5  1  0
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  2  3  1  0
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  5  6  1  0
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 12 13  2  0
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 29 28  1  0
 27 29  1  0
  3  6  2  0
 13 14  1  0
  6  7  1  0
 23 30  1  0
 14 15  2  0
 30 31  1  0
  1  2  2  0
 30 32  1  0
 15 16  1  0
 30 33  1  0
  7  8  1  0
 22 34  1  0
M  CHG  2  22   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA485620

   N-cyclopropyl-1-[3-[6-(2-hydroxypropan-2-yl)-1-oxidopyridin-1-ium-3-yl]phenyl]-4-oxo-1,8-naphthyridine-3-carboxamide

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: 456.50

Molecular Weight (Monoisotopic): 456.1798

AlogP: 2.81

#Rotatable Bonds: 5

Polar Surface Area: 111.16

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.87

CX Basic pKa: 1.86

CX LogP: 1.87

CX LogD: 1.87

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.35

Np Likeness Score: -0.94

References

1. Guay D, Boulet L, Friesen RW, Girard M, Hamel P, Huang Z, Laliberté F, Laliberté S, Mancini JA, Muise E, Pon D, Styhler A..  (2008)  Optimization and structure-activity relationship of a series of 1-phenyl-1,8-naphthyridin-4-one-3-carboxamides: identification of MK-0873, a potent and effective PDE4 inhibitor.,  18  (20): [PMID:18835163] [10.1016/j.bmcl.2008.09.009]

Source

Source(1):

• Scientific Literature