(4-{2-[3-(4-Chloro-phenoxy)-2-hydroxy-propylamino]-ethoxy}-phenoxy)-acetic acid methyl ester HCl

ID: ALA1743906

PubChem CID: 54582793

Max Phase: Preclinical

Molecular Formula: C20H25Cl2NO6

Molecular Weight: 409.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COc1ccc(OCCNCC(O)COc2ccc(Cl)cc2)cc1.Cl

Standard InChI:  InChI=1S/C20H24ClNO6.ClH/c1-25-20(24)14-28-19-8-6-17(7-9-19)26-11-10-22-12-16(23)13-27-18-4-2-15(21)3-5-18;/h2-9,16,22-23H,10-14H2,1H3;1H

Standard InChI Key:  JIHCGVMYAZHZMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   13.0384   -3.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0134   -2.2107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6051   -3.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7634   -4.3482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3301   -3.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0509   -4.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9051   -3.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -5.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -4.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4759   -4.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4801   -4.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6176   -4.3357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7634   -3.4315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051   -6.0065    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0509   -5.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1926   -3.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301   -4.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9009   -4.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176   -4.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3301   -6.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1801   -4.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4801   -3.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1884   -3.5232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7634   -4.7440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9051   -4.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3384   -4.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0509   -4.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4634   -2.9940    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  1  2  0
  3  5  1  0
  4 11  1  0
  5  1  1  0
  6  4  1  0
  7  3  1  0
  8 19  2  0
  9 25  1  0
 10 21  1  0
 11  9  1  0
 12 26  1  0
 13  1  1  0
 14  8  1  0
 15  6  1  0
 16  7  2  0
 17  6  2  0
 18  7  1  0
 19 17  1  0
 20 15  2  0
 21 18  2  0
 22 16  1  0
 23  9  1  0
 24 10  1  0
 25 12  1  0
 26 27  1  0
 27 24  1  0
 28 13  1  0
 10 22  2  0
  8 20  1  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: 409.87

Molecular Weight (Monoisotopic): 409.1292

AlogP: 2.30

#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: 8.79

CX LogP: 2.54

CX LogD: 1.14

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.41

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. 1. [4-[2-[(2-Hydroxy-3-phenoxypropyl)amino]ethoxy]phenoxy]acetates.,  35  (10): [PMID:1350309] [10.1021/jm00088a009]

Source

Source(1):

• Scientific Literature