2-(4'-carbamimidoylbiphenyl-3-yl)-1H-benzo[d]imidazole-6-carboximidamide

ID: ALA1232113

PubChem CID: 11221963

Max Phase: Preclinical

Molecular Formula: C21H18N6

Molecular Weight: 354.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(-c2cccc(-c3nc4ccc(C(=N)N)cc4[nH]3)c2)cc1

Standard InChI:  InChI=1S/C21H18N6/c22-19(23)13-6-4-12(5-7-13)14-2-1-3-16(10-14)21-26-17-9-8-15(20(24)25)11-18(17)27-21/h1-11H,(H3,22,23)(H3,24,25)(H,26,27)

Standard InChI Key:  LRMPNDUSMWYCMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -0.7764   -1.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014   -1.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -1.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014   -0.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7764   -0.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639   -1.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639    0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7764    0.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639    1.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4611    1.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    0.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4611    0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139   -2.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014   -3.3463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8389   -2.6318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    0.2731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681    0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9681    1.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    1.6080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    1.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    0.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1115    0.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8260    0.5280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1115   -0.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
 13  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
 12  7  1  0
  8  9  1  0
 10  9  2  0
 10 11  1  0
 11 12  2  0
 11 16  1  0
 13 14  1  0
 13 15  2  0
 16 17  1  0
 16 20  2  0
 18 17  1  0
 18 19  2  0
 18 24  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1232113

   2-{4'-[amino(Imino)methyl]biphenyl-3-Yl}-1h-Benzimidazole-6-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: 354.42

Molecular Weight (Monoisotopic): 354.1593

AlogP: 3.47

#Rotatable Bonds: 4

Polar Surface Area: 128.42

Molecular Species: BASE

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.40

CX Basic pKa: 11.78

CX LogP: 1.86

CX LogD: -2.02

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: -0.67

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