2-(5-(4-carbamimidoyl-2-methoxyphenyl)furan-2-yl)-1H-indole-6-carboximidamide

ID: ALA4851823

PubChem CID: 164615634

Max Phase: Preclinical

Molecular Formula: C21H19N5O2

Molecular Weight: 373.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C(=N)N)ccc1-c1ccc(-c2cc3ccc(C(=N)N)cc3[nH]2)o1

Standard InChI:  InChI=1S/C21H19N5O2/c1-27-19-10-13(21(24)25)4-5-14(19)17-6-7-18(28-17)16-8-11-2-3-12(20(22)23)9-15(11)26-16/h2-10,26H,1H3,(H3,22,23)(H3,24,25)

Standard InChI Key:  YQPZVFSJQFUJBF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   16.6655  -12.6002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2530  -13.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6655  -14.0277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4280  -13.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0155  -14.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1905  -14.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0155  -12.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1905  -12.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7780  -11.8844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1905  -11.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7780  -13.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9531  -13.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4683  -13.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6837  -13.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6837  -12.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0182  -12.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0182  -11.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2336  -11.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7489  -12.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9265  -11.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5931  -11.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7708  -11.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2861  -11.7478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374  -10.3237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0778  -10.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8960  -10.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2336  -12.6718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4683  -12.6465    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  1  0
  9 10  1  0
  8 11  2  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 21 25  1  0
 25 26  2  0
 18 26  1  0
 19 27  1  0
 16 27  1  0
 15 28  1  0
 12 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4851823

   ---

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: 373.42

Molecular Weight (Monoisotopic): 373.1539

AlogP: 3.67

#Rotatable Bonds: 5

Polar Surface Area: 137.90

Molecular Species: BASE

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.06

CX Basic pKa: 11.33

CX LogP: 1.83

CX LogD: -2.82

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.27

Np Likeness Score: -0.28

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