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

ID: ALA1234147

Cas Number: 869767-86-2

PubChem CID: 11523228

Max Phase: Preclinical

Molecular Formula: C21H18N6

Molecular Weight: 354.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1cccc(-c2ccc(-c3nc4cc(C(=N)N)ccc4[nH]3)cc2)c1

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

Standard InChI Key:  JTEAXLWMBHFLPI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -2.7135   -0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3010    0.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4760    0.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0635   -0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4760   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3010   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2385   -0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1740    0.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115   -0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1740   -1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2365   -0.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135   -2.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5385   -2.0282    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3010   -2.7426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7214    0.0682    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060   -1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7214   -1.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2205   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2205    0.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9349   -0.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9349   -1.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3639   -1.0117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6494   -2.2492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  2  0
  4  7  1  0
  4  5  1  0
  5  6  2  0
 14  6  1  0
  7  8  2  0
 12  7  1  0
  8  9  1  0
 10  9  2  0
 10 13  1  0
 10 11  1  0
 11 12  2  0
 13 20  2  0
 13 17  1  0
 14 16  1  0
 14 15  2  0
 18 17  1  0
 18 22  2  0
 18 19  1  0
 19 21  2  0
 19 20  1  0
 21 24  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1234147

   2-{3'-[Amino(imino)methyl]biphenyl-4-YL}-1H-benzimidazole-5-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: 11.71

CX Basic pKa: 11.19

CX LogP: 2.12

CX LogD: -2.00

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: -0.79

References

1. Gillingwater K, Kumar A, Anbazhagan M, Boykin DW, Tidwell RR, Brun R..  (2009)  In vivo investigations of selected diamidine compounds against Trypanosoma evansi using a mouse model.,  53  (12): [PMID:19786604] [10.1128/aac.00422-09]

2. 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