(4-{2-[3-(3-Fluoro-phenoxy)-2-hydroxy-propylamino]-ethoxy}-phenoxy)-acetic acid methyl ester, 1/4 H2O HCl

ID: ALA1743908

PubChem CID: 54584767

Max Phase: Preclinical

Molecular Formula: C20H25ClFNO6

Molecular Weight: 393.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COc1ccc(OCCNCC(O)COc2cccc(F)c2)cc1.Cl

Standard InChI:  InChI=1S/C20H24FNO6.ClH/c1-25-20(24)14-28-18-7-5-17(6-8-18)26-10-9-22-12-16(23)13-27-19-4-2-3-15(21)11-19;/h2-8,11,16,22-23H,9-10,12-14H2,1H3;1H

Standard InChI Key:  PZWIDWIHGWANRA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   13.4291   -3.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4040   -2.7370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7069   -4.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0011   -3.6096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1348   -4.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7276   -4.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209   -5.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9929   -5.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2997   -4.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711   -4.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8592   -4.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8571   -5.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0033   -4.8664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1556   -3.9603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2789   -4.8914    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.2871   -4.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5815   -3.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8675   -4.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5732   -5.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5628   -4.0522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1452   -5.2755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7069   -6.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2893   -5.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4209   -6.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9929   -6.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7173   -5.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4312   -4.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8570   -3.5219    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  7  2  0
  4  6  1  0
  5 12  1  0
  6  1  1  0
  7  5  1  0
  8  3  1  0
  9  4  1  0
 10 23  1  0
 11 18  2  0
 12 10  1  0
 13 26  1  0
 14  1  1  0
 15  8  1  0
 16  9  1  0
 17  9  2  0
 18 17  1  0
 19 16  2  0
 20 10  1  0
 21 11  1  0
 22 24  2  0
 23 13  1  0
 24  7  1  0
 25 22  1  0
 26 27  1  0
 27 21  1  0
 28 14  1  0
 19 11  1  0
  8 25  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: 393.41

Molecular Weight (Monoisotopic): 393.1588

AlogP: 1.79

#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: 2.07

CX LogD: 0.67

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.04

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