N-{2-[2-(2-Chloro-phenyl)-2-hydroxy-ethylamino]-ethyl}-2-phenyl-acetamide; Fumarate

ID: ALA1794836

PubChem CID: 22769501

Max Phase: Preclinical

Molecular Formula: C22H25ClN2O6

Molecular Weight: 332.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccccc1)NCCNCC(O)c1ccccc1Cl.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C18H21ClN2O2.C4H4O4/c19-16-9-5-4-8-15(16)17(22)13-20-10-11-21-18(23)12-14-6-2-1-3-7-14;5-3(6)1-2-4(7)8/h1-9,17,20,22H,10-13H2,(H,21,23);1-2H,(H,5,6)(H,7,8)/b;2-1+

Standard InChI Key:  FFTZGZLUQCRAAJ-WLHGVMLRSA-N

Molfile:  

     RDKit          2D

 31 31  0  0  0  0  0  0  0  0999 V2000
   -9.8482   -0.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8482    0.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5607    0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8482    0.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1357    0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5607   -0.3082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1357   -0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5649    0.9126    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.7024    0.1001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4149    0.1126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1357    0.9168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8482   -1.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4232   -0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2732   -0.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2732    0.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9857   -0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7024   -0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4232    0.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5607   -1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2732   -1.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7149    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899    0.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9982    0.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8777    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7027    0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1152    1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1152   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9402   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3527   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9402   -1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -17.1777   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  2  0
  4  2  2  0
  5  1  1  0
  6 15  1  0
  7  2  1  0
  8  3  1  0
  9 13  1  0
 10  7  1  0
 11  5  1  0
 12  1  1  0
 13  5  1  0
 14  3  1  0
 15 16  1  0
 16  9  1  0
 17 10  2  0
 18 10  1  0
 19 12  2  0
 20 19  1  0
 21 18  2  0
 22 17  1  0
 23 21  1  0
 20 14  2  0
 23 22  2  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  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: 332.83

Molecular Weight (Monoisotopic): 332.1292

AlogP: 2.32

#Rotatable Bonds: 8

Polar Surface Area: 61.36

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: 8.58

CX LogP: 2.36

CX LogD: 1.15

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: -0.94

References

1. Large MS, Smith LH..  (1980)  Beta-adrenergic blocking agents. 19. 1-Phenyl-2-[[(substituted-amido)alkyl]amino]ethanols.,  23  (2): [PMID:6102152] [10.1021/jm00176a002]

Source

Source(1):

• Scientific Literature