1-[3-(Phenylethynyl)azulen-1-ylmethyl]-4-(2-methoxyphenyl)piperazine

ID: ALA2207633

PubChem CID: 71459759

Max Phase: Preclinical

Molecular Formula: C30H28N2O

Molecular Weight: 432.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(Cc2cc(C#Cc3ccccc3)c3cccccc2-3)CC1

Standard InChI:  InChI=1S/C30H28N2O/c1-33-30-15-9-8-14-29(30)32-20-18-31(19-21-32)23-26-22-25(17-16-24-10-4-2-5-11-24)27-12-6-3-7-13-28(26)27/h2-15,22H,18-21,23H2,1H3

Standard InChI Key:  KMVWYPYWHLOVLW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.3179   -4.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0630   -3.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1249   -5.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6342   -5.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4608   -5.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8029   -4.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9835   -5.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8009   -5.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1257   -4.4068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5092   -3.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4955   -3.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2036   -2.6147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9275   -3.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6335   -2.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6240   -1.7675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9031   -1.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1906   -1.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3310   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0531   -1.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7607   -1.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7475   -0.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0206   -0.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3159   -0.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0659   -2.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7874   -2.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2226   -5.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6469   -6.5782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0716   -7.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6692   -8.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0932   -8.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9197   -8.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3203   -7.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8940   -7.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  1  3  1  0
  3  4  2  0
  7  5  2  0
  4  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
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 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
 19 24  1  0
 24 25  1  0
  8 26  1  0
 26 27  3  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2207633

   1-(2-Methoxyphenyl)-4-[[3-(2-phenylethynyl)azulen-1-yl]methyl]piperazine

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: 432.57

Molecular Weight (Monoisotopic): 432.2202

AlogP: 5.52

#Rotatable Bonds: 4

Polar Surface Area: 15.71

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.86

CX LogP: 6.61

CX LogD: 6.01

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.39

Np Likeness Score: -1.00

References

1. Löber S, Hübner H, Buschauer A, Sanna F, Argiolas A, Melis MR, Gmeiner P..  (2012)  Novel azulene derivatives for the treatment of erectile dysfunction.,  22  (23): [PMID:23099096] [10.1016/j.bmcl.2012.09.064]

Source

Source(1):

• Scientific Literature