Purealin

ID: ALA206161

Max Phase: Preclinical

Molecular Formula: C27H29Br4N7O7

Molecular Weight: 883.19

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Purealin

Canonical SMILES:  COC1=C(Br)[C@@H](O)[C@]2(C=C1Br)CC(C(=O)NCCCOc1c(Br)cc(C/C(=N/O)C(=O)NCCc3c[nH]c(N)n3)cc1Br)=NO2

Standard InChI:  InChI=1S/C27H29Br4N7O7/c1-43-22-17(30)10-27(23(39)20(22)31)11-19(38-45-27)25(41)33-4-2-6-44-21-15(28)7-13(8-16(21)29)9-18(37-42)24(40)34-5-3-14-12-35-26(32)36-14/h7-8,10,12,23,39,42H,2-6,9,11H2,1H3,(H,33,41)(H,34,40)(H3,32,35,36)/b37-18-/t23-,27+/m1/s1

Standard InChI Key:  FFJLRVBPVWKFTA-BAPZPQAKSA-N

Molfile:  

     RDKit          2D

 45 48  0  0  1  0  0  0  0  0999 V2000
   -1.3920    1.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9836    2.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3981    2.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2209    2.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274    2.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2105    1.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5027   -0.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5016   -0.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2164   -1.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9328   -0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9300   -0.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2146    0.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121    1.2086    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7868   -1.2684    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7882    0.3832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3592    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449   -0.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9303    0.3825    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2159   -0.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    0.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161   -0.8552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821    1.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.6627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2492    0.0499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168    0.6557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6397    3.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4647    3.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9895    3.5200    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4523    2.0718    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.6480   -1.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3618   -0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0769   -1.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3605   -0.0288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0743    0.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7907   -0.8515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0782   -2.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5058   -1.2629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2197   -0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9348   -1.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8263   -2.2584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2380   -1.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6772   -0.9244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0192   -2.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0585   -1.4608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 21 23  1  0
  5  6  1  0
 11 12  2  0
 12  7  1  0
  1 23  1  6
  1 24  1  1
 24 25  1  0
 25 21  2  0
  6  1  1  0
  6 26  1  6
 12 13  1  0
  1  2  1  0
 27 28  1  0
  4 27  1  0
  8 14  1  0
  3 29  1  0
  3  4  1  0
  5 30  1  0
  7 15  1  0
 10 31  1  0
  7  8  2  0
 31 32  1  0
 15 16  1  0
 32 33  1  0
 32 34  2  0
 16 17  1  0
 34 35  1  0
  8  9  1  0
 33 36  1  0
 17 18  1  0
 33 37  2  0
  4  5  2  0
 36 38  1  0
 18 19  1  0
 38 39  1  0
  9 10  2  0
 39 40  1  0
 19 20  1  0
  2  3  2  0
 20 21  1  0
 10 11  1  0
 41 42  1  0
 42 43  2  0
 43 40  1  0
 40 44  2  0
 44 41  1  0
 20 22  2  0
 42 45  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA206161

   PUREALIN

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: 883.19

Molecular Weight (Monoisotopic): 878.8862

AlogP: 3.55

#Rotatable Bonds: 13

Polar Surface Area: 205.77

Molecular Species: BASE

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.27

CX Basic pKa: 9.01

CX LogP: 1.62

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.08

Np Likeness Score: 1.20

References

1. Zhu G, Yang F, Balachandran R, Höök P, Vallee RB, Curran DP, Day BW..  (2006)  Synthesis and biological evaluation of purealin and analogues as cytoplasmic dynein heavy chain inhibitors.,  49  (6): [PMID:16539395] [10.1021/jm051030l]

Source

Source(1):

• Scientific Literature