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

ID: ALA1743910

PubChem CID: 54585701

Max Phase: Preclinical

Molecular Formula: C19H23ClFNO6

Molecular Weight: 379.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)COc1ccc(OCCNCC(O)COc2ccccc2F)cc1

Standard InChI:  InChI=1S/C19H22FNO6.ClH/c20-17-3-1-2-4-18(17)27-12-14(22)11-21-9-10-25-15-5-7-16(8-6-15)26-13-19(23)24;/h1-8,14,21-22H,9-13H2,(H,23,24);1H

Standard InChI Key:  QKKWJZBHVSHATC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   13.0650   -3.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7900   -4.6048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0775   -5.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0400   -2.4673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3608   -4.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6358   -3.3340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3608   -3.7215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9358   -3.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -5.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2233   -4.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3608   -3.7840    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.5025   -4.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7900   -3.6840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6483   -4.5923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2233   -3.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9275   -4.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2108   -5.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5108   -3.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2150   -3.7715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7900   -4.9965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9358   -5.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0775   -5.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6483   -5.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3650   -5.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0775   -4.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6483   -5.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3608   -6.2590    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  1  1  0
 14 24  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 14  1  0
 22  3  1  0
 23  5  1  0
 24 25  1  0
 25 20  1  0
 26 27  1  0
 27 22  2  0
 12 18  2  0
 23 26  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: 379.38

Molecular Weight (Monoisotopic): 379.1431

AlogP: 1.70

#Rotatable Bonds: 12

Polar Surface Area: 97.25

Molecular Species: ZWITTERION

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.98

CX Basic pKa: 8.79

CX LogP: -0.54

CX LogD: -0.56

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -0.99

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