4-[Benzyl-(2-naphthylmethyl)-amino]-butyronitrile

ID: ALA566469

PubChem CID: 44473507

Max Phase: Preclinical

Molecular Formula: C22H22N2

Molecular Weight: 314.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCCCN(Cc1ccccc1)Cc1ccc2ccccc2c1

Standard InChI:  InChI=1S/C22H22N2/c23-14-6-7-15-24(17-19-8-2-1-3-9-19)18-20-12-13-21-10-4-5-11-22(21)16-20/h1-5,8-13,16H,6-7,15,17-18H2

Standard InChI Key:  LUOWOCACBZBWAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    5.8994    0.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6114    0.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3286    0.0443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0407    0.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3336   -0.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0508   -1.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0541   -2.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7705   -2.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4835   -2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4758   -1.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7590   -0.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1853    0.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -1.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9091   -0.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0357    1.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -0.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4740    0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7608    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0514    0.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0597   -0.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7735   -1.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7479    1.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7427    2.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7410    3.3502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  2  0
 12 17  1  0
  1  2  1  0
 16 13  1  0
  6  7  2  0
 13 14  2  0
 14  1  1  0
  3  4  1  0
  4 15  1  0
  7  8  1  0
 16 17  1  0
  8  9  2  0
 17 18  2  0
  3  5  1  0
 18 19  1  0
  9 10  1  0
 19 20  2  0
  2  3  1  0
 20 21  1  0
 21 16  2  0
 10 11  2  0
 15 22  1  0
 11  6  1  0
 22 23  1  0
  5  6  1  0
 23 24  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA566469

   4-[Benzyl(naphthalen-2-ylmethyl)amino]butanenitrile

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: 314.43

Molecular Weight (Monoisotopic): 314.1783

AlogP: 5.15

#Rotatable Bonds: 7

Polar Surface Area: 27.03

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.23

CX LogP: 4.69

CX LogD: 3.80

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.56

Np Likeness Score: -1.05

References

1. Valant C, Maillet E, Bourguignon JJ, Bucher B, Utard V, Galzi JL, Hibert M..  (2009)  Allosteric functional switch of neurokinin A-mediated signaling at the neurokinin NK2 receptor: structural exploration.,  52  (19): [PMID:19746979] [10.1021/jm900671k]

Source

Source(1):

• Scientific Literature