Ethyl 5-(3-(4-(4-chlorophenyl)piperazin-1-yl)propoxy)-1Hindole-2-carboxylate

ID: ALA568284

PubChem CID: 45112463

Max Phase: Preclinical

Molecular Formula: C24H28ClN3O3

Molecular Weight: 441.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2cc(OCCCN3CCN(c4ccc(Cl)cc4)CC3)ccc2[nH]1

Standard InChI:  InChI=1S/C24H28ClN3O3/c1-2-30-24(29)23-17-18-16-21(8-9-22(18)26-23)31-15-3-10-27-11-13-28(14-12-27)20-6-4-19(25)5-7-20/h4-9,16-17,26H,2-3,10-15H2,1H3

Standard InChI Key:  WTIUQHNBWSFVMR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    1.4818   -8.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4806   -9.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954  -10.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1936   -8.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9089   -8.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092   -9.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6952  -10.0438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808   -9.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6948   -8.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0057   -9.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4185  -10.0890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4180   -8.6603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2429   -8.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6556   -9.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672   -8.5537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530   -8.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6616   -8.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3759   -8.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904   -8.5544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0919   -7.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8024   -7.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191   -7.7217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5209   -8.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8059   -8.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2297   -7.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2254   -6.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9375   -6.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6544   -6.4788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6547   -7.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9419   -7.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3679   -6.0647    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 18 19  1  0
 19 20  1  0
  9  5  1  0
  4  1  1  0
  8 10  1  0
  5  6  1  0
 10 11  2  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 10 12  1  0
 25 26  2  0
  2  3  1  0
 26 27  1  0
 12 13  1  0
 27 28  2  0
  3  6  2  0
 28 29  1  0
 13 14  1  0
 29 30  2  0
 30 25  1  0
 22 25  1  0
  1  2  2  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA568284

   Ethyl 5-(3-(4-(4-chlorophenyl)piperazin-1-yl)propoxy)-1Hindole-2-carboxylate

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: 441.96

Molecular Weight (Monoisotopic): 441.1819

AlogP: 4.59

#Rotatable Bonds: 8

Polar Surface Area: 57.80

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.58

CX Basic pKa: 7.80

CX LogP: 4.62

CX LogD: 4.07

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: -1.52

References

1. Frecentese F, Fiorino F, Perissutti E, Severino B, Magli E, Esposito A, De Angelis F, Massarelli P, Nencini C, Viti B, Santagada V, Caliendo G..  (2010)  Efficient microwave combinatorial synthesis of novel indolic arylpiperazine derivatives as serotoninergic ligands.,  45  (2): [PMID:19954866] [10.1016/j.ejmech.2009.11.023]

Source

Source(1):

• Scientific Literature