4-(2,3-Bis-hydroxymethyl-6,7-dimethoxy-naphthalen-1-yl)-1-butyl-3,6-dihydro-1H-pyridin-2-one

ID: ALA2115234

PubChem CID: 10763354

Max Phase: Preclinical

Molecular Formula: C23H27NO5

Molecular Weight: 397.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1ccc(-c2c(CO)c(CO)cc3cc(OC)c(OC)cc23)cc1=O

Standard InChI:  InChI=1S/C23H27NO5/c1-4-5-7-24-8-6-15(11-22(24)27)23-18-12-21(29-3)20(28-2)10-16(18)9-17(13-25)19(23)14-26/h6,8-12,25-26H,4-5,7,13-14H2,1-3H3

Standard InChI Key:  GLQDANQNRADIEB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    7.5897   -4.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2980   -3.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0129   -3.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3780   -6.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2980   -2.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5716   -5.9253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7335   -3.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5887   -3.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8927   -5.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7775   -4.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7335   -2.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0129   -2.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8681   -3.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5887   -2.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8681   -2.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2627   -5.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6697   -6.8176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1474   -3.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1361   -2.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4599   -3.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9882   -6.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4713   -2.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4713   -4.7185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4942   -1.4584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4326   -2.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4440   -3.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1989   -6.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041   -6.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8091   -6.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  9  1  0
  5  2  1  0
  6 16  1  0
  7  3  2  0
  8  2  2  0
  9  1  2  0
 10  1  1  0
 11  7  1  0
 12 11  2  0
 13  8  1  0
 14  5  2  0
 15 13  2  0
 16 10  2  0
 17  4  2  0
 18 13  1  0
 19 15  1  0
 20  7  1  0
 21  6  1  0
 22 11  1  0
 23 20  1  0
 24 22  1  0
 25 19  1  0
 26 18  1  0
 27 21  1  0
 28 27  1  0
 29 28  1  0
  6  4  1  0
  5 12  1  0
 15 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115234

   4-[2,3-Bis(hydroxymethyl)-6,7-dimethoxynaphthalen-1-yl]-1-butylpyridin-2-one

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: 397.47

Molecular Weight (Monoisotopic): 397.1889

AlogP: 3.47

#Rotatable Bonds: 8

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.22

CX LogD: 2.22

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: 0.05

References

1. Iwasaki T, Kondo K, Kuroda T, Moritani Y, Yamagata S, Sugiura M, Kikkawa H, Kaminuma O, Ikezawa K..  (1996)  Novel selective PDE IV inhibitors as antiasthmatic agents. Synthesis and biological activities of a series of 1-aryl-2,3-bis(hydroxymethyl)naphthalene lignans.,  39  (14): [PMID:8709099] [10.1021/jm9509096]

2. Iwasaki T, Kondo K, Kuroda T, Moritani Y, Yamagata S, Sugiura M, Kikkawa H, Kaminuma O, Ikezawa K..  (1996)  Novel selective PDE IV inhibitors as antiasthmatic agents. Synthesis and biological activities of a series of 1-aryl-2,3-bis(hydroxymethyl)naphthalene lignans.,  39  (14): [PMID:8709099] [10.1021/jm9509096]

Source

Source(1):

• Scientific Literature