1-{2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-3-phenyl-urea

ID: ALA3392321

PubChem CID: 118725301

Max Phase: Preclinical

Molecular Formula: C19H24N4O4

Molecular Weight: 354.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccccc1OCC(O)CNCCNC(=O)Nc1ccccc1.O

Standard InChI:  InChI=1S/C19H22N4O3.H2O/c20-12-15-6-4-5-9-18(15)26-14-17(24)13-21-10-11-22-19(25)23-16-7-2-1-3-8-16;/h1-9,17,21,24H,10-11,13-14H2,(H2,22,23,25);1H2

Standard InChI Key:  MBZWOQRTHFWTTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    9.3107   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3875   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -3.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1042   -5.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -5.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -5.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3875   -6.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6750   -5.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1000   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8125   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292   -5.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1000   -6.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8125   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -5.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9542   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8000   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5292   -5.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -5.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2375   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5042   -6.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2292   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  3  0
  4  5  1  0
  5  7  1  0
  6  2  1  0
  7  8  1  0
  8 11  1  0
  9  2  2  0
 10  2  1  0
 11 12  1  0
 12 17  1  0
 13  6  1  0
 14 20  1  0
 15 12  1  0
 16  5  2  0
 17 14  1  0
 18  7  2  0
 19 10  1  0
 20 19  1  0
 21 13  1  0
 22 13  2  0
 23 24  2  0
 24 18  1  0
 25 22  1  0
 26 21  2  0
 27 25  2  0
 26 27  1  0
 23 16  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: 354.41

Molecular Weight (Monoisotopic): 354.1692

AlogP: 1.71

#Rotatable Bonds: 9

Polar Surface Area: 106.41

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: 8.79

CX LogP: 1.61

CX LogD: 0.21

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -1.50

References

1. Baldwin JJ, Christy ME, Denny GH, Habecker CN, Freedman MB, Lyle PA, Ponticello GS, Varga SL, Gross DM, Sweet CS..  (1986)  Beta 1-selective adrenoceptor antagonists: examples of the 2-[4-[3-(substituted amino)-2-hydroxypropoxy]phenyl]imidazole class. 2.,  29  (6): [PMID:2872332] [10.1021/jm00156a028]

2. 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]

3. Mistry SN, Baker JG, Fischer PM, Hill SJ, Gardiner SM, Kellam B..  (2013)  Synthesis and in vitro and in vivo characterization of highly β1-selective β-adrenoceptor partial agonists.,  56  (10): [PMID:23614528] [10.1021/jm400348g]

Source

Source(1):

• Scientific Literature