11-(4-Methoxybenzyl)-N9,N9-dimethyl-11H-benzo[g]pyrido[2,3-b]indole-7,9-diamine

ID: ALA552328

PubChem CID: 45271682

Max Phase: Preclinical

Molecular Formula: C25H24N4O

Molecular Weight: 396.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2c3nc(N(C)C)cc(N)c3c3ccc4ccccc4c32)cc1

Standard InChI:  InChI=1S/C25H24N4O/c1-28(2)22-14-21(26)23-20-13-10-17-6-4-5-7-19(17)24(20)29(25(23)27-22)15-16-8-11-18(30-3)12-9-16/h4-14H,15H2,1-3H3,(H2,26,27)

Standard InChI Key:  ZTMTWCYAELCKLX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    3.3015    0.4100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0339    1.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0731    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8064    0.3238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5004    0.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4612    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7280    1.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854    1.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381    1.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671    2.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0434    2.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9618    1.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908    1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7671    1.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3144    1.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6854    0.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5091    0.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888    2.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2337    0.3918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9278    0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2729   -0.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0841   -0.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2862   -0.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0689   -1.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2710   -1.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9078   -0.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057   -0.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1075   -1.2246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3249   -2.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
 14 15  1  0
  6  7  2  0
 15 16  2  0
  7  2  1  0
 16 17  1  0
 17 12  2  0
  2  3  2  0
  7 18  1  0
  2  9  1  0
  5 19  1  0
  8  9  2  0
 19 20  1  0
  3  4  1  0
 19 21  1  0
  9 10  1  0
  1 22  1  0
  8  1  1  0
 22 23  1  0
 10 11  2  0
 23 24  2  0
 11 13  1  0
 24 25  1  0
 12  8  1  0
 25 26  2  0
  4  5  2  0
 26 27  1  0
  1  3  1  0
 27 28  2  0
 28 23  1  0
 12 13  1  0
 26 29  1  0
  5  6  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA552328

   17-[(4-methoxyphenyl)methyl]-14-N,14-N-dimethyl-15,17-diazatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,8,11(16),12,14-octaene-12,14-diamine

Molecule Features

Natural Product: No

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: 396.49

Molecular Weight (Monoisotopic): 396.1950

AlogP: 5.05

#Rotatable Bonds: 4

Polar Surface Area: 56.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.20

CX LogP: 4.89

CX LogD: 4.69

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -0.74

References

1. Willemann C, Grünert R, Bednarski PJ, Troschütz R..  (2009)  Synthesis and cytotoxic activity of 5,6-heteroaromatically annulated pyridine-2,4-diamines.,  17  (13): [PMID:19481463] [10.1016/j.bmc.2009.05.016]

Source

Source(1):

• Scientific Literature