Lipopurealin A

ID: ALA206373

Max Phase: Preclinical

Molecular Formula: C31H48Br2N6O4

Molecular Weight: 728.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCC(=O)NCCCOc1c(Br)cc(C/C(=N/O)C(=O)NCCc2c[nH]c(N)n2)cc1Br

Standard InChI:  InChI=1S/C31H48Br2N6O4/c1-2-3-4-5-6-7-8-9-10-11-12-14-28(40)35-16-13-18-43-29-25(32)19-23(20-26(29)33)21-27(39-42)30(41)36-17-15-24-22-37-31(34)38-24/h19-20,22,42H,2-18,21H2,1H3,(H,35,40)(H,36,41)(H3,34,37,38)/b39-27-

Standard InChI Key:  GKUJVGYRWHGSBN-NOACJBATSA-N

Molfile:  

     RDKit          2D

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    7.3122   -5.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0287   -5.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3080   -3.4330    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.8826   -5.9101    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.8840   -4.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4551   -4.2588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7407   -4.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261   -4.2592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5972   -4.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3119   -5.4968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7438   -5.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1701   -4.2568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8865   -5.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1740   -6.7318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6017   -5.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3155   -5.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0306   -5.9023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9221   -6.9001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3339   -6.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7731   -5.5661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1150   -6.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1544   -6.1025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1186   -4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
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 24 25  1  0
  6  1  1  0
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  1  2  2  0
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  6  7  1  0
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 28 31  1  0
  3  4  2  0
 15 32  1  0
 14 16  2  0
 32 33  1  0
  2  8  1  0
 33 34  1  0
  4 17  1  0
 34 35  1  0
 35 36  1  0
 17 18  1  0
 36 37  1  0
  1  9  1  0
 37 38  1  0
 18 19  1  0
 38 39  1  0
  4  5  1  0
 39 40  1  0
 18 20  2  0
 40 41  1  0
  9 10  1  0
 41 42  1  0
 20 21  1  0
 42 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA206373

   LIPOPUREALIN A

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: 728.57

Molecular Weight (Monoisotopic): 726.2104

AlogP: 6.83

#Rotatable Bonds: 23

Polar Surface Area: 154.72

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.27

CX Basic pKa: 9.01

CX LogP: 6.11

CX LogD: 5.86

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.04

Np Likeness Score: 0.07

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