10,11-dimethoxy-4-methyldibenzo[c,f]-2,7-naphthyridine-3,6-diamine

ID: ALA235157

Cas Number: 936833-38-4

PubChem CID: 17754396

Max Phase: Preclinical

Molecular Formula: C19H18N4O2

Molecular Weight: 334.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2ncc3c(N)nc4c(C)c(N)ccc4c3c2cc1OC

Standard InChI:  InChI=1S/C19H18N4O2/c1-9-13(20)5-4-10-17-11-6-15(24-2)16(25-3)7-14(11)22-8-12(17)19(21)23-18(9)10/h4-8H,20H2,1-3H3,(H2,21,23)

Standard InChI Key:  NVINUNQBDNEMSY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -3.4494   -0.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7349   -1.1201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060   -1.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060   -1.9451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -2.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915   -0.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915    0.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1230    0.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8374    0.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    0.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519    1.3549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664    0.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9808    0.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2664   -0.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9808   -1.1201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5519   -1.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8374   -0.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1230    1.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8374    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8374    2.5924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060    1.3549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3060    0.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204    0.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
 13 14  1  0
 20 12  2  0
 11 12  1  0
 19 20  1  0
 13 11  2  0
 15 13  1  0
 10 11  1  0
 22 19  2  0
  9 19  1  0
 22 23  1  0
 15 16  1  0
 17 15  2  0
 24 23  2  0
  9 10  1  0
 10 18  2  0
  9  8  2  0
  8 24  1  0
 25 24  1  0
 18 17  1  0
  8  7  1  0
  3 25  2  0
  7  4  2  0
  6  5  1  0
  4  3  1  0
  3  2  1  0
  4  5  1  0
  1  2  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA235157

   10,11-Dimethoxy-4-methyldibenzo[c,f]-2,7-naphthyridine-3,6-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: 334.38

Molecular Weight (Monoisotopic): 334.1430

AlogP: 3.43

#Rotatable Bonds: 2

Polar Surface Area: 96.28

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.96

CX LogP: 2.41

CX LogD: 2.40

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: -0.35

References

1. Gopalsamy A, Shi M, Boschelli DH, Williamson R, Olland A, Hu Y, Krishnamurthy G, Han X, Arndt K, Guo B..  (2007)  Discovery of dibenzo[c,f][2,7]naphthyridines as potent and selective 3-phosphoinositide-dependent kinase-1 inhibitors.,  50  (23): [PMID:17941624] [10.1021/jm070851i]

2. Nittoli T, Dushin RG, Ingalls C, Cheung K, Floyd MB, Fraser H, Olland A, Hu Y, Grosu G, Han X, Arndt K, Guo B, Wissner A..  (2010)  The identification of 8,9-dimethoxy-5-(2-aminoalkoxy-pyridin-3-yl)-benzo[c][2,7]naphthyridin-4-ylamines as potent inhibitors of 3-phosphoinositide-dependent kinase-1 (PDK-1).,  45  (4): [PMID:20074837] [10.1016/j.ejmech.2009.12.036]

3. PubChem BioAssay data set, 

4. Medina JR..  (2013)  Selective 3-phosphoinositide-dependent kinase 1 (PDK1) inhibitors: dissecting the function and pharmacology of PDK1.,  56  (7): [PMID:23448267] [10.1021/jm4000227]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays