(2R,3S,4R,5R,6R)-5-amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyloxy)-2-((4-nitrobenzylamino)methyl)tetrahydro-2H-pyran-3,4-diol

ID: ALA4460970

PubChem CID: 155528313

Max Phase: Preclinical

Molecular Formula: C19H31N5O8

Molecular Weight: 457.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N[C@H]1[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](N)C[C@@H]2N)O[C@H](CNCc2ccc([N+](=O)[O-])cc2)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H31N5O8/c20-10-5-11(21)18(17(28)14(10)25)32-19-13(22)16(27)15(26)12(31-19)7-23-6-8-1-3-9(4-2-8)24(29)30/h1-4,10-19,23,25-28H,5-7,20-22H2/t10-,11+,12-,13-,14+,15-,16-,17-,18-,19-/m1/s1

Standard InChI Key:  PQHYEMXJGFIGCM-ITRADPEYSA-N

Molfile:  

 
     RDKit          2D

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   38.6799  -19.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6523  -19.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9296  -18.7015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2343  -19.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   38.0125  -21.1641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3452  -18.6486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5096  -18.7441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4022  -20.2892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5630  -20.3848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8389  -19.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8189  -19.1763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0988  -18.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3974  -19.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4207  -20.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.0767  -17.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8736  -20.8189    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.7204  -20.4663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7772  -17.5369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7572  -16.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4547  -16.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1688  -16.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8659  -16.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8463  -15.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1238  -15.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4298  -15.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5440  -15.0122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.5230  -14.1953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2621  -15.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  2  8  1  1
  4  9  1  1
  1 10  1  6
  5 11  1  6
 11 12  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 15 19  1  6
 14 20  1  1
 12 21  1  1
 16 22  1  1
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 31 32  2  0
 31 33  1  0
 28 31  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4460970

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 457.48

Molecular Weight (Monoisotopic): 457.2173

AlogP: -3.38

#Rotatable Bonds: 7

Polar Surface Area: 232.61

Molecular Species: BASE

HBA: 12

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.66

CX Basic pKa: 9.15

CX LogP: -3.19

CX LogD: -6.73

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.15

Np Likeness Score: 0.59

References

1. Simon B, Walmsley C, Jackson VJ, Garvey EP, Slater MJ, Berrisford DJ, Gardiner JM..  (2019)  Evaluation of neomycin analogues for HIV-1 RRE RNA recognition identifies enhanced activity simplified neamine analogues.,  29  (2): [PMID:30477891] [10.1016/j.bmcl.2018.11.004]

Source

Source(1):

• Scientific Literature