N'-cyano-N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)isonicotinamidine

ID: ALA1099374

PubChem CID: 46861870

Max Phase: Preclinical

Molecular Formula: C21H26N6O

Molecular Weight: 378.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(CCCN/C(=N\C#N)c2ccncc2)CC1

Standard InChI:  InChI=1S/C21H26N6O/c1-28-20-6-3-2-5-19(20)27-15-13-26(14-16-27)12-4-9-24-21(25-17-22)18-7-10-23-11-8-18/h2-3,5-8,10-11H,4,9,12-16H2,1H3,(H,24,25)

Standard InChI Key:  PCSRINCTRTWFDX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -6.3152   -5.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3141   -6.7023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5961   -7.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8797   -6.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8825   -5.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5979   -5.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1696   -5.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4536   -5.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1727   -4.6311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4598   -4.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7451   -3.8006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407   -5.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0247   -5.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117   -5.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5957   -5.8552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5947   -6.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172   -7.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8326   -6.6826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8314   -5.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149   -5.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5470   -7.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5430   -7.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2567   -8.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -7.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9695   -7.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -6.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2508   -5.8547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631   -5.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  5  7  1  0
 14 15  1  0
 15 16  1  0
  3  4  2  0
  7  8  1  0
  7  9  2  0
  4  5  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  9 10  1  0
 18 21  1  0
  2  3  1  0
 21 22  2  0
 10 11  3  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
  8 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 26 21  1  0
 12 13  1  0
 26 27  1  0
  1  2  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099374

   N''-cyano-N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)isonicotinamidine

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: 378.48

Molecular Weight (Monoisotopic): 378.2168

AlogP: 2.12

#Rotatable Bonds: 7

Polar Surface Area: 76.78

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.72

CX LogP: 1.82

CX LogD: 1.33

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.34

Np Likeness Score: -1.47

References

1. Fiorino F, Severino B, De Angelis F, Perissutti E, Magli E, Frecentese F, Esposito A, Massarelli P, Nencini C, Santagada V, Caliendo G..  (2010)  New 5-HT(1A) receptor ligands containing a N'-cyanoisonicotinamidine nucleus: synthesis and in vitro pharmacological evaluation.,  20  (9): [PMID:20347301] [10.1016/j.bmcl.2010.02.106]

Source

Source(1):

• Scientific Literature