1-(4-bromophenyl)-4-(3-(methylphenylacetate-4-yl-oxy)-2-hydroxypropyl)-piperazine

ID: ALA4205279

PubChem CID: 145978303

Max Phase: Preclinical

Molecular Formula: C22H27BrN2O4

Molecular Weight: 463.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Cc1ccc(OCC(O)CN2CCN(c3ccc(Br)cc3)CC2)cc1

Standard InChI:  InChI=1S/C22H27BrN2O4/c1-28-22(27)14-17-2-8-21(9-3-17)29-16-20(26)15-24-10-12-25(13-11-24)19-6-4-18(23)5-7-19/h2-9,20,26H,10-16H2,1H3

Standard InChI Key:  UVNUFDMBXRXOSI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    2.0581  -27.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0569  -28.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7650  -28.5301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4746  -28.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4718  -27.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632  -26.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7607  -26.0755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4672  -25.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1762  -26.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8826  -25.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1786  -26.8885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5916  -26.0671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5884  -26.8812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933  -27.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0022  -26.8804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0017  -26.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2923  -25.6514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7082  -27.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7063  -28.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4128  -28.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1218  -28.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1198  -27.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4127  -26.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7648  -29.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0570  -29.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0568  -30.5729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494  -29.3469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415  -29.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8297  -28.5167    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 10 12  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
  3 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4205279

   ---

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: 463.37

Molecular Weight (Monoisotopic): 462.1154

AlogP: 2.73

#Rotatable Bonds: 8

Polar Surface Area: 62.24

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.48

CX LogP: 3.49

CX LogD: 3.15

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: -1.12

References

1. Huang JJ, Zhang ZH, He F, Liu XW, Xu XJ, Dai LJ, Liu QM, Yuan M..  (2018)  Novel naftopidil derivatives containing methyl phenylacetate and their blocking effects on α1D/1A-adrenoreceptor subtypes.,  28  (4): [PMID:29422390] [10.1016/j.bmcl.2018.01.068]

Source

Source(1):

• Scientific Literature