(2R,6S)-1-allyl-4-hydroxy-2,6-bis(4-nitrophenyl)-1,2,3,6-tetrahydropyridine-3,5-dicarboxylate

ID: ALA559644

Max Phase: Preclinical

Molecular Formula: C26H27N3O9

Molecular Weight: 525.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCN1[C@@H](c2ccc([N+](=O)[O-])cc2)C(C(=O)OCC)=C(O)C(C(=O)OCC)[C@@H]1c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C26H27N3O9/c1-4-15-27-22(16-7-11-18(12-8-16)28(33)34)20(25(31)37-5-2)24(30)21(26(32)38-6-3)23(27)17-9-13-19(14-10-17)29(35)36/h4,7-14,20,22-23,30H,1,5-6,15H2,2-3H3/t20?,22-,23-/m0/s1

Standard InChI Key:  AUPLBCVICPSTAQ-FALYVICWSA-N

Molfile:  

     RDKit          2D

 38 40  0  0  0  0  0  0  0  0999 V2000
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  8  9  1  0
  5 18  1  0
  2  3  1  0
 18 19  1  0
  9 10  2  0
 18 20  2  0
  3  4  1  0
 10 11  1  0
 19 22  1  0
  4  5  1  0
 22 23  1  0
 11 12  2  0
  1 24  1  0
 12  7  1  0
 24 25  2  0
  2  7  1  1
 24 26  1  0
  5  6  2  0
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 27 28  1  0
 13 14  2  0
  3 29  1  0
  1  2  1  0
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 14 15  1  0
 30 31  2  0
  7  8  2  0
 15 16  2  0
  1  6  1  0
 32 33  2  0
 32 34  1  0
 10 32  1  0
 16 17  1  0
 17 21  2  0
 21 13  1  0
 35 36  2  0
 35 37  1  0
 16 35  1  0
  4 13  1  6
  6 38  1  0
M  CHG  4  32   1  34  -1  35   1  37  -1
M  END

Alternative Forms

1. Parent:

   

   ALA559644

   ---

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: 525.51

Molecular Weight (Monoisotopic): 525.1747

AlogP: 4.34

#Rotatable Bonds: 10

Polar Surface Area: 162.35

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.21

CX Basic pKa: 5.15

CX LogP: 4.40

CX LogD: 4.33

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.20

Np Likeness Score: -0.53

References

1. Niedermeier S, Singethan K, Rohrer SG, Matz M, Kossner M, Diederich S, Maisner A, Schmitz J, Hiltensperger G, Baumann K, Holzgrabe U, Schneider-Schaulies J..  (2009)  A small-molecule inhibitor of Nipah virus envelope protein-mediated membrane fusion.,  52  (14): [PMID:19499921] [10.1021/jm900411s]

Source

Source(1):

• Scientific Literature