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

ID: ALA1743911

PubChem CID: 54583784

Max Phase: Preclinical

Molecular Formula: C20H25ClFNO6

Molecular Weight: 393.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COc1cccc(OCCNCC(O)COc2ccccc2F)c1.Cl

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

Standard InChI Key:  OGBMCUSOKMGGTC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   12.6373   -5.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586   -4.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464   -5.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6415   -5.9137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301   -4.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7762   -5.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2047   -5.0934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9169   -4.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4926   -4.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0707   -5.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0683   -4.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829   -4.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9218   -3.8690    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2072   -4.6811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3494   -4.6686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7829   -3.8648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3561   -5.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7804   -3.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5033   -5.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464   -5.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -5.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5008   -3.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0683   -3.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9318   -5.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6440   -4.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0658   -5.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2179   -5.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301   -6.3510    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 10  1  0
  3  2  1  0
  4  1  2  0
  5  3  2  0
  6  9  2  0
  7  8  1  0
  8  1  1  0
  9  7  1  0
 10 12  1  0
 11  6  1  0
 12 19  1  0
 13  5  1  0
 14 24  1  0
 15  1  1  0
 16 12  1  0
 17 11  1  0
 18 22  2  0
 19 14  1  0
 20  3  1  0
 21  5  1  0
 22  9  1  0
 23 18  1  0
 24 25  1  0
 25 17  1  0
 26 15  1  0
 27 28  1  0
 28 20  2  0
 11 23  2  0
 21 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: 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: 8.76

CX LogP: 2.07

CX LogD: 0.70

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.08

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