4,4'-(oxazole-2,5-diyl)dibenzimidamide

ID: ALA1181011

PubChem CID: 12207737

Max Phase: Preclinical

Molecular Formula: C17H15N5O

Molecular Weight: 305.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(-c2cnc(-c3ccc(C(=N)N)cc3)o2)cc1

Standard InChI:  InChI=1S/C17H15N5O/c18-15(19)11-3-1-10(2-4-11)14-9-22-17(23-14)13-7-5-12(6-8-13)16(20)21/h1-9H,(H3,18,19)(H3,20,21)

Standard InChI Key:  PQMRTHBIHQTMLW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    4.6792   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792   -5.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -6.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2042   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9167   -6.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -6.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2042   -7.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -6.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1375   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9917   -6.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -6.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4250   -7.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -5.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3542   -7.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -5.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042   -6.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -5.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5542   -6.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6 13  1  0
  7 12  1  0
  8  6  2  0
  9  7  2  0
 10  1  1  0
 11  4  1  0
 12 21  1  0
 13 20  1  0
 14 10  2  0
 15 10  1  0
 16 11  2  0
 17 11  1  0
 18 16  1  0
 19 14  1  0
 20 17  2  0
 21 15  2  0
 22  7  1  0
 23  6  1  0
  4  5  2  0
 19 12  2  0
 18 13  2  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1181011

   4-[2-(4-Carbamimidoylphenyl)-1,3-oxazol-5-yl]benzenecarboximidamide;dihydrochloride

2. Parent:

   

   ALA1181011

   4-[2-(4-Carbamimidoylphenyl)-1,3-oxazol-5-yl]benzenecarboximidamide

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: 305.34

Molecular Weight (Monoisotopic): 305.1277

AlogP: 2.58

#Rotatable Bonds: 4

Polar Surface Area: 125.77

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 11.23

CX LogP: 1.35

CX LogD: -3.42

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.44

Np Likeness Score: -0.50

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