(R)-4-(2-Hydroxy-3-((2-(2-methoxyphenoxy)ethyl)amino)-propyl)benzene-1,2-diol

ID: ALA4518727

PubChem CID: 155541417

Max Phase: Preclinical

Molecular Formula: C18H23NO5

Molecular Weight: 333.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1OCCNC[C@H](O)Cc1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C18H23NO5/c1-23-17-4-2-3-5-18(17)24-9-8-19-12-14(20)10-13-6-7-15(21)16(22)11-13/h2-7,11,14,19-22H,8-10,12H2,1H3/t14-/m1/s1

Standard InChI Key:  RHQUUSAPEMUYFD-CQSZACIVSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    5.1266  -12.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8369  -11.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5503  -12.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2605  -11.6383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9739  -12.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6801  -11.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8338  -10.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132  -11.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4141  -10.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016  -10.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9903  -10.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9960  -11.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091  -12.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3934  -12.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1037  -11.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2805  -10.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913  -12.0733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8154  -12.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5252  -11.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5226  -10.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8043  -10.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0974  -10.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3824  -10.4033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3761   -9.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  1
  1  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  6 14  1  0
 14 15  1  0
 11 16  1  0
 12 17  1  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 15  1  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4518727

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 333.38

Molecular Weight (Monoisotopic): 333.1576

AlogP: 1.68

#Rotatable Bonds: 9

Polar Surface Area: 91.18

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.63

CX Basic pKa: 8.97

CX LogP: 1.56

CX LogD: 0.32

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.41

Np Likeness Score: 0.25

References

1. Stanek M, Picard LP, Schmidt MF, Kaindl JM, Hübner H, Bouvier M, Weikert D, Gmeiner P..  (2019)  Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias.,  62  (10): [PMID:31042379] [10.1021/acs.jmedchem.9b00349]

Source

Source(1):

• Scientific Literature