{4-[2-(2-Hydroxy-3-phenoxy-propylamino)-propoxy]-phenoxy}-acetic acid methyl ester HCl

ID: ALA2115011

PubChem CID: 71459994

Max Phase: Preclinical

Molecular Formula: C21H29NO7

Molecular Weight: 389.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)COc1ccc(OCC(C)NCC(O)COc2ccccc2)cc1.O

Standard InChI:  InChI=1S/C21H27NO6.H2O/c1-16(22-12-17(23)14-27-18-6-4-3-5-7-18)13-26-19-8-10-20(11-9-19)28-15-21(24)25-2;/h3-11,16-17,22-23H,12-15H2,1-2H3;1H2

Standard InChI Key:  JAKVTMKNRDQQKS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.2125    0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875    1.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7917   -1.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792    0.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -1.5292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0625   -1.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -0.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3625   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -1.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9375   -0.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6500   -0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625    0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3625   -0.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6375    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4958   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -2.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4958   -2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -2.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4 22  1  0
  5  8  1  0
  6 10  1  0
  7 13  1  0
  8  2  1  0
  9 12  1  0
 10 19  2  0
 11  5  1  0
 12  4  1  0
 13  9  1  0
 14  2  1  0
 15  7  1  0
 16  6  1  0
 17 18  2  0
 18 11  1  0
 19 20  1  0
 20 11  2  0
 21  9  1  0
 22 16  1  0
 23 14  1  0
 24 15  2  0
 25 15  1  0
 26 22  1  0
 27 25  2  0
 28 24  1  0
 29 27  1  0
 17 10  1  0
 28 29  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: 389.45

Molecular Weight (Monoisotopic): 389.1838

AlogP: 2.04

#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: 8.87

CX LogP: 2.35

CX LogD: 0.87

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -0.62

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