17,20,23-trioxa-4,12,14,26,28-pentaazahexacyclo[24.6.1.17,14.02,6.08,13.027,32]tetratriaconta-1(33),2(6),7(34),8,10,12,27,29,31-nonaene-3,5-dione

ID: ALA340776

PubChem CID: 10141037

Max Phase: Preclinical

Molecular Formula: C26H25N5O5

Molecular Weight: 487.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)C2=C1c1cn(c3ncccc13)CCOCCOCCOCCn1cc2c2cccnc21

Standard InChI:  InChI=1S/C26H25N5O5/c32-25-21-19-15-30(23-17(19)3-1-5-27-23)7-9-34-11-13-36-14-12-35-10-8-31-16-20(22(21)26(33)29-25)18-4-2-6-28-24(18)31/h1-6,15-16H,7-14H2,(H,29,32,33)

Standard InChI Key:  POFRSIZMPZFXPB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
    8.3042   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0667   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7625   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0875   -2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9917   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7625   -1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875   -0.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6792   -2.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -3.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -4.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4250   -3.2875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9792   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4000   -3.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250   -3.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5667   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8125   -2.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -4.4375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6042   -0.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375   -1.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5875   -5.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4917   -6.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6292   -5.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6292   -4.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4917   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9792   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2250   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3042   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4250   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3917   -5.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0167   -6.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8292   -6.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6792   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8125   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -3.2625    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 29  1  0
 21 34  1  0
 22 30  1  0
 23 11  1  0
 24 10  1  0
 25 14  2  0
 26 15  2  0
 27 36  2  0
 28 35  2  0
 29 24  1  0
 30 23  1  0
 31 20  1  0
 32 33  1  0
 33 22  1  0
 34 31  1  0
 35 26  1  0
 36 25  1  0
  7  5  1  0
 10 13  1  0
 11 12  1  0
 27 17  1  0
 16 28  1  0
 32 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA340776

   17,20,23-Trioxa-4,12,14,26,28-pentazahexacyclo[24.6.1.17,14.02,6.08,13.027,32]tetratriaconta-1(33),2(6),7(34),8(13),9,11,27(32),28,30-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: 487.52

Molecular Weight (Monoisotopic): 487.1856

AlogP: 2.02

#Rotatable Bonds: ┄

Polar Surface Area: 109.50

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.71

CX Basic pKa: 3.68

CX LogP: 1.33

CX LogD: 1.33

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.38

Np Likeness Score: -0.38

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. Saraswati AP, Ali Hussaini SM, Krishna NH, Babu BN, Kamal A..  (2018)  Glycogen synthase kinase-3 and its inhibitors: Potential target for various therapeutic conditions.,  144  [PMID:29306837] [10.1016/j.ejmech.2017.11.103]

3. Winfield HJ, Cahill MM, O'Shea KD, Pierce LT, Robert T, Ruchaud S, Bach S, Marchand P, McCarthy FO..  (2018)  Synthesis and anticancer activity of novel bisindolylhydroxymaleimide derivatives with potent GSK-3 kinase inhibition.,  26  (14): [PMID:30026041] [10.1016/j.bmc.2018.07.012]

Source

Source(1):

• Scientific Literature