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

ID: ALA2115015

PubChem CID: 15174930

Max Phase: Preclinical

Molecular Formula: C21H28N2O6

Molecular Weight: 404.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H28N2O6/c24-12-10-23-21(26)16-29-20-8-6-19(7-9-20)27-13-11-22-14-17(25)15-28-18-4-2-1-3-5-18/h1-9,17,22,24-25H,10-16H2,(H,23,26)/t17-/m0/s1

Standard InChI Key:  CJXVAOIYYFPZDN-KRWDZBQOSA-N

Molfile:  

     RDKit          2D

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   13.1143  -10.0595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4615   -8.6232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -8.6574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8719   -9.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6408   -8.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7191   -8.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9994   -8.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0067   -9.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1440   -8.6346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876   -9.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2247   -7.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4098   -9.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4098   -7.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7077   -7.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1661   -9.3414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4372   -9.0507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9408   -8.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8621   -9.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3511   -9.3414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5745   -8.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8694   -8.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876   -9.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513   -9.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8694  -10.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513   -9.9056    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 20  1  0
  9 16  1  0
 10  8  1  0
 11 22  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 23  1  0
 20 11  1  0
 21  3  1  0
 22 24  1  0
 23 21  1  0
 24 18  1  0
 25 12  2  0
 26 12  1  0
 27 25  1  0
 28 26  2  0
 29 28  1  0
  9 15  2  0
 29 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115015

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

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: 404.46

Molecular Weight (Monoisotopic): 404.1947

AlogP: 0.58

#Rotatable Bonds: 14

Polar Surface Area: 109.28

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.96

CX Basic pKa: 8.79

CX LogP: 0.51

CX LogD: -0.89

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -0.80

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