3,N*8*,N*8*-Trimethyl-phenazine-2,8-diamine

ID: ALA278037

Cas Number: 366-13-2

PubChem CID: 11106

Max Phase: Preclinical

Molecular Formula: C15H16N4

Molecular Weight: 252.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2nc3ccc(N(C)C)cc3nc2cc1N

Standard InChI:  InChI=1S/C15H16N4/c1-9-6-13-15(8-11(9)16)18-14-7-10(19(2)3)4-5-12(14)17-13/h4-8H,16H2,1-3H3

Standard InChI Key:  GLVRJEJEXGVOMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    4.4375   -2.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -3.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -2.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -2.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -2.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3125   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5875   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  1  2  0
  4  1  1  0
  5  3  1  0
  6  3  1  0
  7  4  2  0
  8  4  1  0
  9  7  1  0
 10  6  2  0
 11  5  1  0
 12 10  1  0
 13  9  1  0
 14 15  1  0
 15  8  2  0
 16 10  1  0
 17 12  1  0
 18 13  1  0
 19 13  1  0
  5  2  2  0
 14  9  2  0
 12 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA278037

   Neutral Red Base

Molecule Features

Natural Product: Yes

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: 252.32

Molecular Weight (Monoisotopic): 252.1375

AlogP: 2.74

#Rotatable Bonds: 1

Polar Surface Area: 55.04

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.10

CX LogP: 2.85

CX LogD: 2.85

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.53

Np Likeness Score: -0.95

References

1. Wang W, Préville P, Morin N, Mounir S, Cai W, Siddiqui MA..  (2000)  Hepatitis C viral IRES inhibition by phenazine and phenazine-like molecules.,  10  (11): [PMID:10866369] [10.1016/s0960-894x(00)00217-1]

2. Gordon CP, Keller PA..  (2005)  Control of hepatitis C: a medicinal chemistry perspective.,  48  (1): [PMID:15633995] [10.1021/jm0400101]

3. PubChem BioAssay data set, 

4. Dibrov SM, Parsons J, Carnevali M, Zhou S, Rynearson KD, Ding K, Garcia Sega E, Brunn ND, Boerneke MA, Castaldi MP, Hermann T..  (2014)  Hepatitis C virus translation inhibitors targeting the internal ribosomal entry site.,  57  (5): [PMID:24138284] [10.1021/jm401312n]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays