(4-{2-[3-(2-Chloro-phenoxy)-2-hydroxy-propylamino]-ethoxy}-phenoxy)-acetic acid methyl ester HCl

ID: ALA1743909

PubChem CID: 54584768

Max Phase: Preclinical

Molecular Formula: C20H25Cl2NO6

Molecular Weight: 409.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COc1ccc(OCCNCC(O)COc2ccccc2Cl)cc1.Cl

Standard InChI:  InChI=1S/C20H24ClNO6.ClH/c1-25-20(24)14-27-17-8-6-16(7-9-17)26-11-10-22-12-15(23)13-28-19-5-3-2-4-18(19)21;/h2-9,15,22-23H,10-14H2,1H3;1H

Standard InChI Key:  DSQLGSHHPYGONN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   12.7732   -3.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5065   -4.5252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940   -4.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7565   -2.3877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -4.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3482   -3.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0732   -3.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6482   -3.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232   -4.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9357   -4.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -3.7085    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2190   -4.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3607   -4.5127    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5065   -3.6085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9357   -3.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6440   -4.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9232   -4.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2232   -3.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9315   -3.7002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5065   -4.9210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6482   -4.9335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7940   -5.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607   -4.9460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0815   -4.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7940   -4.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2065   -3.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3607   -5.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -6.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4161   -7.8080    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  3  2  1  0
  4  1  2  0
  5  3  2  0
  6  7  1  0
  7  1  1  0
  8  6  1  0
  9 10  1  0
 10 21  1  0
 11  5  1  0
 12 17  1  0
 13 24  1  0
 14  1  1  0
 15  8  2  0
 16  8  1  0
 17 16  2  0
 18 15  1  0
 19 10  1  0
 20 12  1  0
 21 13  1  0
 22  3  1  0
 23  5  1  0
 24 25  1  0
 25 20  1  0
 26 14  1  0
 27 28  1  0
 28 22  2  0
 12 18  2  0
 23 27  2  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: 409.87

Molecular Weight (Monoisotopic): 409.1292

AlogP: 2.30

#Rotatable Bonds: 12

Polar Surface Area: 86.25

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 2.54

CX LogD: 1.14

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -0.91

References

1. Howe R, Rao BS, Holloway BR, Stribling D..  (1992)  Selective beta 3-adrenergic agonists of brown adipose tissue and thermogenesis. 1. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetates.,  35  (10): [PMID:1350309] [10.1021/jm00088a009]

Source

Source(1):

• Scientific Literature