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

ID: ALA2207634

PubChem CID: 71459760

Max Phase: Preclinical

Molecular Formula: C27H30N2O

Molecular Weight: 398.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC#Cc1cc(CN2CCN(c3ccccc3OC)CC2)c2cccccc1-2

Standard InChI:  InChI=1S/C27H30N2O/c1-3-4-6-11-22-20-23(25-13-8-5-7-12-24(22)25)21-28-16-18-29(19-17-28)26-14-9-10-15-27(26)30-2/h5,7-10,12-15,20H,3-4,16-19,21H2,1-2H3

Standard InChI Key:  RSTJJQONPRJAIE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   15.8986   -4.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6433   -4.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7059   -5.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2148   -6.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0408   -6.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3826   -4.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5630   -5.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3798   -5.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7042   -4.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0883   -4.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0746   -3.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7821   -3.1085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5054   -3.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2108   -3.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2013   -2.2619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4810   -1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7692   -2.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9076   -1.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6292   -2.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3363   -1.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3231   -0.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5968   -0.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8927   -1.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6421   -3.0646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3628   -3.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8011   -6.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2251   -7.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6494   -7.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2489   -8.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6732   -9.2050    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
 10  6  2  0
 10 11  1  0
 11 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
 19 24  1  0
 24 25  1  0
  8 26  1  0
 26 27  3  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2207634

   1-(2-Methoxyphenyl)-4-[(3-pent-1-ynylazulen-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: 398.55

Molecular Weight (Monoisotopic): 398.2358

AlogP: 5.27

#Rotatable Bonds: 5

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: 7.93

CX LogP: 6.36

CX LogD: 5.72

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: -0.78

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