N-(3-(4-allylpiperazin-1-yl)propyl)-N'-cyanoisonicotinamidine

ID: ALA1086797

PubChem CID: 46889150

Max Phase: Preclinical

Molecular Formula: C17H24N6

Molecular Weight: 312.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1CCN(CCCN/C(=N\C#N)c2ccncc2)CC1

Standard InChI:  InChI=1S/C17H24N6/c1-2-9-22-11-13-23(14-12-22)10-3-6-20-17(21-15-18)16-4-7-19-8-5-16/h2,4-5,7-8H,1,3,6,9-14H2,(H,20,21)

Standard InChI Key:  JPWCKVPTGCWGMZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -5.7056    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7068    0.1977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9919   -0.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2755    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784    1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9937    1.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5654    1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8494    1.0341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5686    2.2689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8556    2.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1409    3.0994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365    1.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205    1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076    1.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0084    1.0448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0095    0.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7214   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4367    0.2174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4356    1.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191    1.4576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512   -0.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512   -1.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656   -1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  8 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  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  1  0
 10 11  3  0
 22 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1086797

   N-cyano-N'-[3-(4-prop-2-enylpiperazin-1-yl)propyl]pyridine-4-carboximidamide

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: 312.42

Molecular Weight (Monoisotopic): 312.2062

AlogP: 1.09

#Rotatable Bonds: 7

Polar Surface Area: 67.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.03

CX LogP: 0.81

CX LogD: 0.10

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.27

Np Likeness Score: -1.34

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