17,20,23,26-tetraoxa-4,12,14,29,31-pentaazahexacyclo[27.6.1.17,14.02,6.08,13.030,35]heptatriaconta-1(36),2(6),7(37),8,10,12,30,32,34-nonaene-3,5-dione

ID: ALA337642

PubChem CID: 10143231

Max Phase: Preclinical

Molecular Formula: C28H29N5O6

Molecular Weight: 531.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C2=C1c1cn(c3ncccc13)CCOCCOCCOCCOCCn1cc2c2cccnc21

Standard InChI:  InChI=1S/C28H29N5O6/c34-27-23-21-17-32(25-19(21)3-1-5-29-25)7-9-36-11-13-38-15-16-39-14-12-37-10-8-33-18-22(24(23)28(35)31-27)20-4-2-6-30-26(20)33/h1-6,17-18H,7-16H2,(H,31,34,35)

Standard InChI Key:  GJJAFPBCJBFVII-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
    5.3042   -0.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9875    0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792    0.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6750   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000   -2.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4167   -1.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042   -1.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -2.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000    1.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292    0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5792   -4.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4917   -5.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0042   -2.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3417   -4.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6250   -2.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2167   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3000   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4167   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8250   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792   -5.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3917   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0167   -4.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0542   -3.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5792   -2.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  2  1  0
  6  1  1  0
  7  6  1  0
  8  3  2  0
  9  4  2  0
 10  9  1  0
 11  8  1  0
 12 15  1  0
 13 14  1  0
 14  4  1  0
 15  3  1  0
 16 12  2  0
 17 13  2  0
 18  5  2  0
 19  6  2  0
 20 30  1  0
 21 33  1  0
 22 31  1  0
 23 36  1  0
 24 10  1  0
 25 11  1  0
 26 15  2  0
 27 14  2  0
 28 39  2  0
 29 38  2  0
 30 24  1  0
 31 25  1  0
 32 35  1  0
 33 34  1  0
 34 20  1  0
 35 21  1  0
 36 37  1  0
 37 22  1  0
 38 27  1  0
 39 26  1  0
  7  5  1  0
 10 13  1  0
 11 12  1  0
 29 17  1  0
 16 28  1  0
 32 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA337642

   17,20,23,26-Tetraoxa-4,12,14,29,31-pentazahexacyclo[27.6.1.17,14.02,6.08,13.030,35]heptatriaconta-1(36),2(6),7(37),8(13),9,11,30(35),31,33-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: 531.57

Molecular Weight (Monoisotopic): 531.2118

AlogP: 2.03

#Rotatable Bonds: ┄

Polar Surface Area: 118.73

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.71

CX Basic pKa: 3.68

CX LogP: 1.29

CX LogD: 1.28

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.34

Np Likeness Score: -0.36

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]

2. Meijer L, Flajolet M, Greengard P..  (2004)  Pharmacological inhibitors of glycogen synthase kinase 3.,  25  (9): [PMID:15559249] [10.1016/j.tips.2004.07.006]

Source

Source(1):

• Scientific Literature