1-[2-(3-Diisopropylamino-2-hydroxy-propoxy)-phenyl]-3-naphthalen-1-yl-propan-1-one

ID: ALA357023

PubChem CID: 10598909

Max Phase: Preclinical

Molecular Formula: C28H35NO3

Molecular Weight: 433.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)N(CC(O)COc1ccccc1C(=O)CCc1cccc2ccccc12)C(C)C

Standard InChI:  InChI=1S/C28H35NO3/c1-20(2)29(21(3)4)18-24(30)19-32-28-15-8-7-14-26(28)27(31)17-16-23-12-9-11-22-10-5-6-13-25(22)23/h5-15,20-21,24,30H,16-19H2,1-4H3

Standard InChI Key:  UXLNGOOPOYAJCH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    6.4042    0.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8375    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9875   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500    0.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -0.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9750    1.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5625   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -2.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167    0.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7042   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125    1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792    1.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8375    0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042   -0.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4042   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4042    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  1  1  0
  5  7  1  0
  6  8  1  0
  7 16  1  0
  8 11  1  0
  9  3  1  0
 10  3  2  0
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 14  4  1  0
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 16 14  1  0
 17 14  1  0
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 19 20  1  0
 20  8  2  0
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 22 19  2  0
 23  5  2  0
 24 15  2  0
 25 12  1  0
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 27 13  1  0
 28 13  1  0
 29 31  2  0
 30 21  1  0
 31 23  1  0
 32 30  2  0
 18 29  1  0
 22 15  1  0
 32 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA357023

   1-(2-(3-(Diisopropylamino)-2-hydroxypropoxy)phenyl)-3-(naphthalen-1-yl)propan-1-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: 433.59

Molecular Weight (Monoisotopic): 433.2617

AlogP: 5.51

#Rotatable Bonds: 11

Polar Surface Area: 49.77

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.13

CX LogP: 5.58

CX LogD: 3.85

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -0.57

References

1. Fleischer R, Wiese M..  (2003)  Three-dimensional quantitative structure-activity relationship analysis of propafenone-type multidrug resistance modulators: influence of variable selection on test set predictivity.,  46  (23): [PMID:14584949] [10.1021/jm030876r]

2. Kaiser D, Terfloth L, Kopp S, Schulz J, de Laet R, Chiba P, Ecker GF, Gasteiger J..  (2007)  Self-organizing maps for identification of new inhibitors of P-glycoprotein.,  50  (7): [PMID:17352460] [10.1021/jm060604z]

Source

Source(1):

• Scientific Literature