7-{[(6,6-Dimethyl-hept-2-en-4-ynyl)-methyl-amino]-methyl}-benzo[b]thiophene-3-carbonitrile hydrochloride

ID: ALA542037

PubChem CID: 45262783

Max Phase: Preclinical

Molecular Formula: C20H23ClN2S

Molecular Weight: 322.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C/C=C/C#CC(C)(C)C)Cc1cccc2c(C#N)csc12.Cl

Standard InChI:  InChI=1S/C20H22N2S.ClH/c1-20(2,3)11-6-5-7-12-22(4)14-16-9-8-10-18-17(13-21)15-23-19(16)18;/h5,7-10,15H,12,14H2,1-4H3;1H/b7-5+;

Standard InChI Key:  UOHPFTPKQUBGEX-GZOLSCHFSA-N

Molfile:  

     RDKit          2D

 24 24  0  0  0  0  0  0  0  0999 V2000
    5.1521    3.6227    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -2.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8749    8.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1713    9.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5579   -3.7661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971    3.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5785    7.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4677    9.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842    6.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935    3.7700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2878    5.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4631   10.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5094    9.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5045   10.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3352    3.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  5  1  0
  4  5  1  0
  3  6  2  0
  2  7  1  0
  4  7  2  0
  4  8  1  0
  9 10  3  0
  8 11  3  0
  6 12  1  0
  9 13  1  0
 10 14  1  0
 13 15  2  0
 12 16  1  0
  6 17  1  0
  5 18  2  0
 15 19  1  0
 16 19  1  0
 17 20  2  0
 18 20  1  0
 14 21  1  0
 14 22  1  0
 14 23  1  0
 16 24  1  0
M  END

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: 322.48

Molecular Weight (Monoisotopic): 322.1504

AlogP: 4.81

#Rotatable Bonds: 4

Polar Surface Area: 27.03

Molecular Species: BASE

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.58

CX LogP: 5.27

CX LogD: 4.06

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: -0.44

References

1. Nussbaumer P, Petranyi G, Stütz A..  (1991)  Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics.,  34  (1): [PMID:1992153] [10.1021/jm00105a011]

Source

Source(1):

• Scientific Literature