4,4'-(furan-2,5-diyl)bis(N-(4-nitrophenethyl)benzimidamide)

ID: ALA4866925

PubChem CID: 164625060

Max Phase: Preclinical

Molecular Formula: C34H30N6O5

Molecular Weight: 602.65

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(NCCc1ccc([N+](=O)[O-])cc1)c1ccc(-c2ccc(-c3ccc(C(=N)NCCc4ccc([N+](=O)[O-])cc4)cc3)o2)cc1

Standard InChI:  InChI=1S/C34H30N6O5/c35-33(37-21-19-23-1-13-29(14-2-23)39(41)42)27-9-5-25(6-10-27)31-17-18-32(45-31)26-7-11-28(12-8-26)34(36)38-22-20-24-3-15-30(16-4-24)40(43)44/h1-18H,19-22H2,(H2,35,37)(H2,36,38)

Standard InChI Key:  KFPMRVVVUHYWOY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 45 49  0  0  0  0  0  0  0  0999 V2000
   18.4629  -13.3284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7514  -12.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7514  -12.0911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4629  -11.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4629  -10.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1787  -10.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1787   -9.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8903   -9.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6061   -9.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3219   -9.2040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0334   -9.6165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3219   -8.3791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6061  -10.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8903  -10.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0356  -13.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0356  -14.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3198  -14.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3198  -12.9159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6041  -13.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6041  -14.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8925  -14.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8035  -15.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9976  -15.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5852  -14.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7671  -14.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2783  -15.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4602  -15.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1269  -14.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3047  -14.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7848  -15.1433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9711  -15.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4512  -15.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6376  -15.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1177  -16.1657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3040  -16.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0061  -15.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924  -15.1370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6725  -15.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987  -14.3659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5259  -14.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3396  -14.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0109  -13.7301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6074  -13.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4296  -14.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1382  -14.2324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  1  0
 13 14  2  0
  6 14  1  0
  2 15  1  0
 15 16  1  0
 16 17  2  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 17 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 36 40  1  0
 40 41  2  0
 33 41  1  0
 29 42  2  0
 28 43  1  0
 43 44  2  0
 25 44  1  0
 24 45  1  0
 21 45  1  0
M  CHG  4  10   1  11  -1  37   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4866925

   ---

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: 602.65

Molecular Weight (Monoisotopic): 602.2278

AlogP: 6.75

#Rotatable Bonds: 12

Polar Surface Area: 171.18

Molecular Species: BASE

HBA: 7

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 11.20

CX LogP: 6.55

CX LogD: 1.79

Aromatic Rings: 5

Heavy Atoms: 45

QED Weighted: 0.05

Np Likeness Score: -0.43

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