2-(5-(4-carbamimidoyl-2-methylphenyl)furan-2-yl)-1H-benzo[d]imidazole-6-carboximidamide

ID: ALA1650569

PubChem CID: 53325855

Max Phase: Preclinical

Molecular Formula: C20H18N6O

Molecular Weight: 358.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: DB850 | CHEMBL1650569|SCHEMBL14599572|DB850

Canonical SMILES:  Cc1cc(C(=N)N)ccc1-c1ccc(-c2nc3ccc(C(=N)N)cc3[nH]2)o1

Standard InChI:  InChI=1S/C20H18N6O/c1-10-8-11(18(21)22)2-4-13(10)16-6-7-17(27-16)20-25-14-5-3-12(19(23)24)9-15(14)26-20/h2-9H,1H3,(H3,21,22)(H3,23,24)(H,25,26)

Standard InChI Key:  MZIXJEWLHNYTIE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    9.0971   -2.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0958   -3.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8088   -4.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5282   -3.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5251   -2.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8069   -2.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3807   -4.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667   -3.6308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3795   -4.8694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2372   -2.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9053   -2.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5743   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3220   -1.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4969   -1.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2836   -2.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3726   -3.6154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0374   -2.4679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5849   -3.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1722   -3.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5764   -4.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3933   -4.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8041   -3.7850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3975   -3.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8037   -5.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3890   -5.9239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6287   -5.2130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8030   -1.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  2  7  1  0
 12 15  1  0
 15 16  1  0
  3  4  2  0
  7  8  2  0
 16 19  1  0
 18 17  1  0
 17 15  2  0
  7  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  5 10  1  0
 20 21  2  0
 10 11  1  0
 21 22  1  0
  2  3  1  0
 22 23  2  0
 23 18  1  0
  5  6  2  0
 21 24  1  0
  6  1  1  0
 24 25  1  0
  1  2  2  0
 24 26  2  0
 11 12  1  0
  6 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1650569

   2-[5-(4-carbamimidoyl-2-methylphenyl)furan-2-yl]-3H-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: 358.41

Molecular Weight (Monoisotopic): 358.1542

AlogP: 3.37

#Rotatable Bonds: 4

Polar Surface Area: 141.56

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.21

CX Basic pKa: 11.59

CX LogP: 0.54

CX LogD: -2.53

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: -0.74

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