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

ID: ALA4215889

PubChem CID: 145971621

Max Phase: Preclinical

Molecular Formula: C23H30N2O5

Molecular Weight: 414.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Cc1ccc(OCC(O)CN2CCN(c3ccccc3OC)CC2)cc1

Standard InChI:  InChI=1S/C23H30N2O5/c1-28-22-6-4-3-5-21(22)25-13-11-24(12-14-25)16-19(26)17-30-20-9-7-18(8-10-20)15-23(27)29-2/h3-10,19,26H,11-17H2,1-2H3

Standard InChI Key:  QBMBZYSVGFDWTF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.9912   -3.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6992   -4.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4089   -3.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4060   -2.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6974   -2.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6950   -1.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4015   -1.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1104   -1.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8169   -1.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1128   -2.3686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5258   -1.5472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5227   -2.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2275   -2.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9364   -2.3606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9359   -1.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2266   -1.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6425   -2.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6405   -3.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3470   -3.9967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0561   -3.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0541   -2.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3470   -2.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6990   -4.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9912   -5.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9910   -6.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2836   -4.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5758   -5.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9320   -3.9949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2251   -3.5850    0.0000 C   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
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 15 16  1  0
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 18 19  2  0
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 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
 19 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4215889

   ---

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: 414.50

Molecular Weight (Monoisotopic): 414.2155

AlogP: 1.97

#Rotatable Bonds: 9

Polar Surface Area: 71.47

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.25

CX LogP: 2.57

CX LogD: 2.33

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.63

Np Likeness Score: -1.02

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