3-(5-(4-carbamimidoylphenyl)thiophen-2-yl)quinoline-6-carboximidamide

ID: ALA4875205

PubChem CID: 164626322

Max Phase: Preclinical

Molecular Formula: C21H17N5S

Molecular Weight: 371.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(-c2ccc(-c3cnc4ccc(C(=N)N)cc4c3)s2)cc1

Standard InChI:  InChI=1S/C21H17N5S/c22-20(23)13-3-1-12(2-4-13)18-7-8-19(27-18)16-10-15-9-14(21(24)25)5-6-17(15)26-11-16/h1-11H,(H3,22,23)(H3,24,25)

Standard InChI Key:  LLNKXSQKKKXTOP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   16.8644  -11.7830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5269  -12.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0116  -13.2028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7087  -12.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3711  -13.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5530  -13.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2240  -11.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4017  -12.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0683  -12.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2459  -12.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8334  -13.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0274  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9385  -12.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2267  -12.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5109  -12.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7992  -12.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0834  -12.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3675  -12.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6516  -12.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9400  -12.1937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6516  -13.4312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3675  -11.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0834  -10.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7992  -11.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5109  -10.9562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2267  -11.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6929  -12.2686    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  4  7  2  0
  7  8  1  0
  8  9  2  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 18 22  1  0
 22 23  2  0
 16 24  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 14 26  1  0
 13 27  1  0
 10 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875205

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 371.47

Molecular Weight (Monoisotopic): 371.1205

AlogP: 4.20

#Rotatable Bonds: 4

Polar Surface Area: 112.63

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 11.62

CX LogP: 3.04

CX LogD: -1.76

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: -0.57

References

1. Depauw S, Lambert M, Jambon S, Paul A, Peixoto P, Nhili R, Marongiu L, Figeac M, Dassi C, Paul-Constant C, Billoré B, Kumar A, Farahat AA, Ismail MA, Mineva E, Sweat DP, Stephens CE, Boykin DW, Wilson WD, David-Cordonnier MH..  (2019)  Heterocyclic Diamidine DNA Ligands as HOXA9 Transcription Factor Inhibitors: Design, Molecular Evaluation, and Cellular Consequences in a HOXA9-Dependant Leukemia Cell Model.,  62  (3.0): [PMID:30645099] [10.1021/acs.jmedchem.8b01448]

Source

Source(1):

• Scientific Literature