4-methyl-17,20-dioxa-4,12,14,23-tetraazahexacyclo[21.6.1.17,14.02,6.08,13.024,29]hentriaconta-1(30),2(6),7(31),8,10,12,24,26,28-nonaene-3,5-dione

ID: ALA340889

PubChem CID: 10874150

Max Phase: Preclinical

Molecular Formula: C26H24N4O4

Molecular Weight: 456.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)C2=C(C1=O)c1cn(c3ncccc13)CCOCCOCCn1cc2c2ccccc21

Standard InChI:  InChI=1S/C26H24N4O4/c1-28-25(31)22-19-15-29(21-7-3-2-5-17(19)21)9-11-33-13-14-34-12-10-30-16-20(23(22)26(28)32)18-6-4-8-27-24(18)30/h2-8,15-16H,9-14H2,1H3

Standard InChI Key:  QEIGKHVPYODGDV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   -2.1583   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -0.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3708   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6458   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8375   -2.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -2.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083   -3.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1167   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1958   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1958   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -2.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708   -0.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875   -5.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250   -4.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125    0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0292   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1500   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -0.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9125   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9125   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -3.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -5.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6250   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6250   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  5  1  0
  4  2  1  0
  5  1  1  0
  6  2  1  0
  7  1  1  0
  8  6  2  0
  9  8  1  0
 10  7  2  0
 11 10  1  0
 12 13  1  0
 13  6  1  0
 14  7  1  0
 15 14  1  0
 16 12  2  0
 17  4  2  0
 18  5  2  0
 19 29  1  0
 20 28  1  0
 21  3  1  0
 22  9  1  0
 23 11  1  0
 24 13  2  0
 25 14  2  0
 26 15  2  0
 27 32  2  0
 28 22  1  0
 29 23  1  0
 30 19  1  0
 31 30  1  0
 32 24  1  0
 33 25  1  0
 34 33  2  0
  3  4  1  0
 11 15  1  0
  9 12  1  0
 34 26  1  0
 16 27  1  0
 31 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA340889

   4-Methyl-17,20-dioxa-4,12,14,23-tetrazahexacyclo[21.6.1.17,14.02,6.08,13.024,29]hentriaconta-1(30),2(6),7(31),8(13),9,11,24,26,28-nonaene-3,5-dione

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: 456.50

Molecular Weight (Monoisotopic): 456.1798

AlogP: 2.95

#Rotatable Bonds: ┄

Polar Surface Area: 78.59

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.38

CX LogP: 2.45

CX LogD: 2.45

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.38

Np Likeness Score: -0.51

References

1. Kuo GH, Prouty C, DeAngelis A, Shen L, O'Neill DJ, Shah C, Connolly PJ, Murray WV, Conway BR, Cheung P, Westover L, Xu JZ, Look RA, Demarest KT, Emanuel S, Middleton SA, Jolliffe L, Beavers MP, Chen X..  (2003)  Synthesis and discovery of macrocyclic polyoxygenated bis-7-azaindolylmaleimides as a novel series of potent and highly selective glycogen synthase kinase-3beta inhibitors.,  46  (19): [PMID:12954055] [10.1021/jm030115o]

Source

Source(1):

• Scientific Literature