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

ID: ALA2115018

PubChem CID: 15174977

Max Phase: Preclinical

Molecular Formula: C22H30N2O7

Molecular Weight: 434.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCNC(=O)COc1ccc(OCCNC[C@H](O)COc2ccc(O)cc2)cc1

Standard InChI:  InChI=1S/C22H30N2O7/c1-28-12-11-24-22(27)16-31-21-8-6-19(7-9-21)29-13-10-23-14-18(26)15-30-20-4-2-17(25)3-5-20/h2-9,18,23,25-26H,10-16H2,1H3,(H,24,27)/t18-/m0/s1

Standard InChI Key:  UGETVXMFKSSLKM-SFHVURJKSA-N

Molfile:  

     RDKit          2D

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   12.9769   -6.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9946   -5.0456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3305   -5.0515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1513   -5.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7436   -5.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4984   -5.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4314   -5.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5735   -5.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0016   -5.0693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4314   -6.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9974   -5.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2651   -4.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2651   -5.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5558   -4.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2656   -6.7629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1438   -5.4587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1191   -4.3197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2817   -5.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8444   -5.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7157   -5.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4356   -5.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2693   -4.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5499   -3.5821    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 12  1  0
  6  1  1  0
  7  4  1  0
  8  5  1  0
  9 26  1  0
 10 18  2  0
 11 21  2  0
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 15  7  1  0
 16  8  2  0
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 18 16  1  0
 19 14  2  0
 20 15  2  0
 21 17  1  0
  9 22  1  1
 23 10  1  0
 24 11  1  0
 25 30  1  0
 26 13  1  0
 27  3  1  0
 28 29  1  0
 29 24  1  0
 30 27  1  0
 31 25  1  0
 11 20  1  0
 19 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115018

   2-[4-[2-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethoxy]phenoxy]-N-(2-methoxyethyl)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: 434.49

Molecular Weight (Monoisotopic): 434.2053

AlogP: 0.94

#Rotatable Bonds: 15

Polar Surface Area: 118.51

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.92

CX Basic pKa: 8.76

CX LogP: 0.60

CX LogD: -0.55

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -0.75

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