N-(2-Hydroxy-1-methyl-ethyl)-2-{4-[2-(2-hydroxy-3-phenoxy-propylamino)-ethoxy]-phenoxy}-acetamide

ID: ALA2113709

PubChem CID: 71461675

Max Phase: Preclinical

Molecular Formula: C22H32N2O7

Molecular Weight: 418.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CO)NC(=O)COc1ccc(OCCNCC(O)COc2ccccc2)cc1.O

Standard InChI:  InChI=1S/C22H30N2O6.H2O/c1-17(14-25)24-22(27)16-30-21-9-7-20(8-10-21)28-12-11-23-13-18(26)15-29-19-5-3-2-4-6-19;/h2-10,17-18,23,25-26H,11-16H2,1H3,(H,24,27);1H2

Standard InChI Key:  XCLWTTRYZOAMTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.6014   -4.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9650   -3.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3768   -2.7682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3768   -4.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7238   -2.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5280   -2.7968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1356   -3.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8889   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9521   -2.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2531   -2.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3877   -2.7682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8074   -3.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4771   -2.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6535   -3.4717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6535   -2.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464   -1.9618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5382   -3.1629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2004   -2.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4358   -3.4831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6728   -3.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083   -3.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6122   -3.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8176   -2.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0867   -2.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8074   -4.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6122   -2.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0867   -4.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3775   -3.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3775   -4.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  2  0
  5  7  1  0
  6 11  1  0
  7  2  1  0
  8  5  1  0
  9 22  1  0
 10 17  1  0
 11  9  1  0
 12 23  1  0
 13  6  1  0
 14  8  2  0
 15  8  1  0
 16 14  1  0
 17 15  2  0
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 20  3  1  0
 21 24  1  0
 22 12  1  0
 23 25  1  0
 24 20  1  0
 25 19  1  0
 26 13  2  0
 27 13  1  0
 28 20  1  0
 29 27  2  0
 30 26  1  0
 31 29  1  0
 10 16  2  0
 31 30  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: 418.49

Molecular Weight (Monoisotopic): 418.2104

AlogP: 0.97

#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: 13.38

CX Basic pKa: 8.79

CX LogP: 0.93

CX LogD: -0.47

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -0.76

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