1-{2-[3-(2-Acetyl-phenoxy)-2-hydroxy-propylamino]-ethyl}-3-phenyl-urea; compound with oxalic acid

ID: ALA3392258

PubChem CID: 13030934

Max Phase: Preclinical

Molecular Formula: C22H27N3O8

Molecular Weight: 371.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccccc1OCC(O)CNCCNC(=O)Nc1ccccc1.O=C(O)C(=O)O

Standard InChI:  InChI=1S/C20H25N3O4.C2H2O4/c1-15(24)18-9-5-6-10-19(18)27-14-17(25)13-21-11-12-22-20(26)23-16-7-3-2-4-8-16;3-1(4)2(5)6/h2-10,17,21,25H,11-14H2,1H3,(H2,22,23,26);(H,3,4)(H,5,6)

Standard InChI Key:  SZXCDXZDRDNXQX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 33  0  0  0  0  0  0  0  0999 V2000
    5.5098   -6.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3348   -6.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7473   -7.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7473   -5.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0973   -5.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0973   -7.4029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9542   -3.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -3.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -2.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875   -2.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -3.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6750   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -3.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -2.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -3.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -3.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3792   -3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1000   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1000   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3792   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1042   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  2  0
  1  6  1  0
  8 11  1  0
  9  7  1  0
 10  8  1  0
 11 12  1  0
 12 16  1  0
 13  7  2  0
 14 10  2  0
 15  7  1  0
 16 17  1  0
 17 22  1  0
 18  9  1  0
 19 26  1  0
 20 17  1  0
 21  8  2  0
 22 19  1  0
 23 10  1  0
 24 11  2  0
 25 15  1  0
 26 25  1  0
 27 18  1  0
 28 18  2  0
 29 21  1  0
 30 24  1  0
 31 28  1  0
 32 27  2  0
 33 31  2  0
 33 32  1  0
 29 30  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: 371.44

Molecular Weight (Monoisotopic): 371.1845

AlogP: 2.04

#Rotatable Bonds: 10

Polar Surface Area: 99.69

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.46

CX Basic pKa: 8.69

CX LogP: 1.31

CX LogD: 0.00

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.38

Np Likeness Score: -1.10

References

1. Lare MS, Smith LH..  (1982)  Beta-adrenergic blocking agents. 22. 1-Phenoxy-3-[[(substituted-amido) alkyl]amino]-2-propanols.,  25  (11): [PMID:6128420] [10.1021/jm00353a004]

Source

Source(1):

• Scientific Literature