2-(4'-carbamimidoylbiphenyl-4-yl)-3a,7a-dihydro-1H-indole-5-carboximidamide

ID: ALA4866451

PubChem CID: 164619660

Max Phase: Preclinical

Molecular Formula: C22H21N5

Molecular Weight: 355.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N=C(N)C1=CC2C=C(c3ccc(-c4ccc(C(=N)N)cc4)cc3)NC2C=C1

Standard InChI:  InChI=1S/C22H21N5/c23-21(24)16-7-3-14(4-8-16)13-1-5-15(6-2-13)20-12-18-11-17(22(25)26)9-10-19(18)27-20/h1-12,18-19,27H,(H3,23,24)(H3,25,26)

Standard InChI Key:  RMVMFNCWHWVTPF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   17.1359  -12.1355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4200  -11.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7042  -12.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7042  -12.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9883  -13.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9883  -11.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2767  -12.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2767  -12.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4920  -13.2177    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4920  -11.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0073  -12.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1823  -12.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7698  -13.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9448  -13.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7698  -11.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9448  -11.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5323  -12.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7073  -12.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2948  -13.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4698  -13.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0573  -12.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2323  -12.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8199  -11.8364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8199  -13.2639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4698  -11.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2948  -11.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4200  -10.8980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  3  6  2  0
  6  7  1  0
  7  8  1  0
  5  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  2  0
 15 16  1  0
 16 17  2  0
 14 17  1  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
  2 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4866451

   ---

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: 355.45

Molecular Weight (Monoisotopic): 355.1797

AlogP: 3.00

#Rotatable Bonds: 4

Polar Surface Area: 111.77

Molecular Species: BASE

HBA: 3

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 12.02

CX LogP: 1.65

CX LogD: -3.72

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.43

Np Likeness Score: 0.21

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