(R)-N-benzyl-2-(3-(2-(2-hydroxy-2-(4-hydroxy-3-(hydroxymethyl)phenyl)ethylamino)ethyl)phenyl)acetamide

ID: ALA230203

PubChem CID: 11247541

Max Phase: Preclinical

Molecular Formula: C26H30N2O4

Molecular Weight: 434.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1cccc(CCNC[C@H](O)c2ccc(O)c(CO)c2)c1)NCc1ccccc1

Standard InChI:  InChI=1S/C26H30N2O4/c29-18-23-15-22(9-10-24(23)30)25(31)17-27-12-11-19-7-4-8-21(13-19)14-26(32)28-16-20-5-2-1-3-6-20/h1-10,13,15,25,27,29-31H,11-12,14,16-18H2,(H,28,32)/t25-/m0/s1

Standard InChI Key:  CWTXUHVXNNFEPT-VWLOTQADSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
   -3.2723    1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2734    0.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586    0.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8422    0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8450    1.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    2.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9882    0.5857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1321    2.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4161    1.8341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352    3.0689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968    2.2492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0128    1.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7258    2.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4418    1.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4420    1.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1572    0.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8711    1.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8653    1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1495    2.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    2.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2942    1.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002    1.0400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0056    2.2826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7231    1.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4345    2.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1486    1.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8595    2.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8540    3.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1315    3.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4235    3.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5588   -0.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2734   -0.6525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  5  8  1  0
 16 17  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
 19 14  1  0
  4  5  1  0
 18 20  1  0
  8 10  1  1
 20 21  1  0
  2  3  1  0
 21 22  2  0
  9 11  1  0
 21 23  1  0
  5  6  2  0
 23 24  1  0
 11 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 12 13  1  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 13 14  1  0
 28 29  1  0
  2  7  1  0
 29 30  2  0
 30 25  1  0
 14 15  2  0
  3 31  1  0
  3  4  2  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA230203

   (R)-N-benzyl-2-(3-(2-(2-hydroxy-2-(4-hydroxy-3-(hydroxymethyl)phenyl)ethylamino)ethyl)phenyl)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: 434.54

Molecular Weight (Monoisotopic): 434.2206

AlogP: 2.61

#Rotatable Bonds: 11

Polar Surface Area: 101.82

Molecular Species: BASE

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.09

CX Basic pKa: 9.37

CX LogP: 2.10

CX LogD: 0.47

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: -0.25

References

1. Brown AD, Bunnage ME, Glossop PA, James K, Jones R, Lane CA, Lewthwaite RA, Mantell S, Perros-Huguet C, Price DA, Trevethick M, Webster R..  (2007)  The discovery of long acting beta2-adrenoreceptor agonists.,  17  (14): [PMID:17498952] [10.1016/j.bmcl.2007.04.081]

Source

Source(1):

• Scientific Literature