2-(5-(4-carbamimidoylphenyl)furan-2-yl)-1H-indole-5-carboximidamide

ID: ALA4854793

PubChem CID: 164615146

Max Phase: Preclinical

Molecular Formula: C20H17N5O

Molecular Weight: 343.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(-c2ccc(-c3cc4cc(C(=N)N)ccc4[nH]3)o2)cc1

Standard InChI:  InChI=1S/C20H17N5O/c21-19(22)12-3-1-11(2-4-12)17-7-8-18(26-17)16-10-14-9-13(20(23)24)5-6-15(14)25-16/h1-10,25H,(H3,21,22)(H3,23,24)

Standard InChI Key:  ZTQVYHXORMQGLC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   16.8100  -13.4077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3265  -12.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6591  -11.9872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5063  -12.8285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1695  -13.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3451  -13.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0186  -12.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1984  -12.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8616  -12.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0414  -13.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6300  -13.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8217  -13.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7330  -12.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0189  -12.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2623  -12.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7105  -12.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8876  -12.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4720  -11.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6491  -11.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2335  -10.6864    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2335  -12.1187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8876  -10.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7105  -10.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1262  -11.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9344  -11.5725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4855  -12.4716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  4  7  2  0
  7  8  1  0
  8  9  2  0
  6  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 18 22  1  0
 22 23  2  0
 16 24  2  0
 23 24  1  0
 24 25  1  0
 14 25  1  0
 13 26  1  0
 10 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4854793

   ---

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: 343.39

Molecular Weight (Monoisotopic): 343.1433

AlogP: 3.66

#Rotatable Bonds: 4

Polar Surface Area: 128.67

Molecular Species: BASE

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.48

CX Basic pKa: 11.46

CX LogP: 2.11

CX LogD: -2.68

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.29

Np Likeness Score: -0.34

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