2-{4-[2-(2-Hydroxy-3-phenoxy-propylamino)-ethoxy]-phenoxy}-N-methyl-acetamide

ID: ALA2115016

PubChem CID: 15174917

Max Phase: Preclinical

Molecular Formula: C20H26N2O5

Molecular Weight: 374.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)COc1ccc(OCCNC[C@H](O)COc2ccccc2)cc1

Standard InChI:  InChI=1S/C20H26N2O5/c1-21-20(24)15-27-19-9-7-18(8-10-19)25-12-11-22-13-16(23)14-26-17-5-3-2-4-6-17/h2-10,16,22-23H,11-15H2,1H3,(H,21,24)/t16-/m0/s1

Standard InChI Key:  RXAULKXJKGDDNG-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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   13.9997  -10.1020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9997   -8.6711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3456   -8.6597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1439   -8.6940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7577   -9.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5100   -8.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5690   -8.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8730   -8.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8592   -9.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0056   -8.6711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -9.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0979   -9.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0979   -7.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2737   -9.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2737   -7.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5632   -7.8641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1576   -9.0660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2902   -9.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7267   -9.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8239   -8.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4365   -8.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015   -8.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -9.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9918   -9.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015  -10.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9918   -9.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  6  1  0
  5 10  1  0
  6  1  1  0
  4  7  1  0
  8 19  1  0
  9 16  1  0
 10  8  1  0
 11 20  1  0
 12  5  1  0
 13  7  2  0
 14  7  1  0
 15 13  1  0
 16 14  2  0
  8 17  1  1
 18  9  1  0
 19 11  1  0
 20 22  1  0
 21  3  1  0
 22 18  1  0
 23 12  2  0
 24 12  1  0
 25 23  1  0
 26 24  2  0
 27 26  1  0
  9 15  2  0
 27 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115016

   2-[4-[2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]ethoxy]phenoxy]-N-methylacetamide

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: 374.44

Molecular Weight (Monoisotopic): 374.1842

AlogP: 1.22

#Rotatable Bonds: 12

Polar Surface Area: 89.05

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.79

CX LogP: 1.20

CX LogD: -0.20

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: -0.87

References

1. Howe R, Rao BS, Holloway BR, Stribling D..  (1992)  Selective beta 3-adrenergic agonists of brown adipose tissue and thermogenesis. 2. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetamides.,  35  (10): [PMID:1350310] [10.1021/jm00088a010]

Source

Source(1):

• Scientific Literature