[1-(3-Amino-4,5-dimethoxy-phenyl)-6,7-diethoxy-3-hydroxymethyl-naphthalen-2-yl]-methanol hydrochloride

ID: ALA542178

Cas Number: 710275-71-1

PubChem CID: 10717370

Max Phase: Preclinical

Molecular Formula: C24H30ClNO6

Molecular Weight: 427.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cc2cc(CO)c(CO)c(-c3cc(N)c(OC)c(OC)c3)c2cc1OCC.Cl

Standard InChI:  InChI=1S/C24H29NO6.ClH/c1-5-30-20-9-14-7-16(12-26)18(13-27)23(17(14)11-21(20)31-6-2)15-8-19(25)24(29-4)22(10-15)28-3;/h7-11,26-27H,5-6,12-13,25H2,1-4H3;1H

Standard InChI Key:  FFPIBIWSDYHXRG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    7.6872    2.2443    0.0000 Cl  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
   -1.2919    2.9980    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
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2844    5.9982    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
   -2.5853    5.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127    5.2449    0.0000 C   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
   -2.5891    3.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089    3.7449    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
    1.2964   -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
   -3.6230    5.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775    7.4991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3159    5.9894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911    1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.5017    0.0000 O   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
   -3.9091   -1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9506    0.8952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072   -2.7019    0.0000 O   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
    3.8890   -3.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2359    8.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3528    5.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9270    3.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9270   -3.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  3  6  2  0
  2  8  2  0
  7  9  2  0
  7 10  1  0
  6 11  1  0
  4 12  2  0
  9 12  1  0
  4 13  1  0
 10 13  2  0
  5 14  1  0
 11 14  2  0
  8 15  1  0
  5 16  2  0
 15 17  2  0
 16 17  1  0
  9 18  1  0
  7 19  1  0
 10 20  1  0
 15 21  1  0
 17 22  1  0
  6 23  1  0
 11 24  1  0
 23 25  1  0
 24 26  1  0
 21 27  1  0
 22 28  1  0
 19 29  1  0
 20 30  1  0
 27 31  1  0
 28 32  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: 427.50

Molecular Weight (Monoisotopic): 427.1995

AlogP: 3.89

#Rotatable Bonds: 9

Polar Surface Area: 103.40

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.66

CX LogP: 2.33

CX LogD: 2.33

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: 0.45

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]

Source

Source(1):

• Scientific Literature