Bis-(5-pyridin-3-yl-thiophen-2-ylmethyl)-amine

ID: ALA178711

PubChem CID: 11210706

Max Phase: Preclinical

Molecular Formula: C20H17N3S2

Molecular Weight: 363.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1cncc(-c2ccc(CNCc3ccc(-c4cccnc4)s3)s2)c1

Standard InChI:  InChI=1S/C20H17N3S2/c1-3-15(11-21-9-1)19-7-5-17(24-19)13-23-14-18-6-8-20(25-18)16-4-2-10-22-12-16/h1-12,23H,13-14H2

Standard InChI Key:  CKCZUAVVHJHNJY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    1.9542    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    0.8583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125    0.8583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1208    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625    0.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -1.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3875   -1.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.9708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3875    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -0.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  7  1  0
  4  1  1  0
  5  1  2  0
  6 10  1  0
  7 19  1  0
  8  4  1  0
  9  5  1  0
 10  7  2  0
 11  1  1  0
 12  2  1  0
 13 17  2  0
 14 16  2  0
 15 18  1  0
 16 12  1  0
 17 11  1  0
 18  8  1  0
 19 15  1  0
 20 11  2  0
 21 12  2  0
 22 24  2  0
 23 25  2  0
 24 20  1  0
 25 21  1  0
  9  8  2  0
 22 13  1  0
  6  2  2  0
 23 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA178711

   Bis-(5-pyridin-3-yl-thiophen-2-ylmethyl)-amine

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: 363.51

Molecular Weight (Monoisotopic): 363.0864

AlogP: 5.22

#Rotatable Bonds: 6

Polar Surface Area: 37.81

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.65

CX LogP: 3.93

CX LogD: 2.67

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -1.07

References

1. Denton TT, Zhang X, Cashman JR..  (2005)  5-substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6.,  48  (1): [PMID:15634016] [10.1021/jm049696n]

2.  (2013)  Synthetic compounds and derivatives as modulators of smoking or nicotine ingestion and lung cancer, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data