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

ID: ALA1743905

PubChem CID: 54587720

Max Phase: Preclinical

Molecular Formula: C20H26ClNO7

Molecular Weight: 391.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COc1ccc(OCCNCC(O)COc2ccc(O)cc2)cc1.Cl

Standard InChI:  InChI=1S/C20H25NO7.ClH/c1-25-20(24)14-28-19-8-6-17(7-9-19)26-11-10-21-12-16(23)13-27-18-4-2-15(22)3-5-18;/h2-9,16,21-23H,10-14H2,1H3;1H

Standard InChI Key:  RFBMRJNPONTCJH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   11.6206   -3.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5957   -2.8894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1921   -3.7598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3502   -5.0259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9168   -4.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -5.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4925   -4.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745   -5.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2096   -6.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0599   -5.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0624   -5.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2071   -5.0134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3453   -4.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4842   -5.0259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -6.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7720   -3.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -5.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217   -6.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2096   -5.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0599   -4.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7678   -5.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745   -4.2013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5109   -6.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3477   -5.4215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4949   -5.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9234   -5.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6356   -5.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0449   -3.6723    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  1  2  0
  3  5  1  0
  4 11  1  0
  5  1  1  0
  6  4  1  0
  7  3  1  0
  8 25  1  0
  9 19  2  0
 10 20  2  0
 11  8  1  0
 12 26  1  0
 13  1  1  0
 14  7  1  0
 15  6  1  0
 16  7  2  0
 17  6  2  0
 18 15  2  0
 19 17  1  0
 20 16  1  0
 21 14  2  0
 22  8  1  0
 23  9  1  0
 24 10  1  0
 25 12  1  0
 26 27  1  0
 27 24  1  0
 28 13  1  0
 21 10  1  0
  9 18  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: 391.42

Molecular Weight (Monoisotopic): 391.1631

AlogP: 1.35

#Rotatable Bonds: 12

Polar Surface Area: 106.48

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.95

CX Basic pKa: 8.76

CX LogP: 1.37

CX LogD: 0.23

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.37

Np Likeness Score: -0.37

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