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

ID: ALA4443278

PubChem CID: 155516407

Max Phase: Preclinical

Molecular Formula: C19H33N5O6

Molecular Weight: 427.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1cccc(CNC[C@H]2O[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](N)C[C@@H]3N)[C@H](N)[C@@H](O)[C@@H]2O)c1

Standard InChI:  InChI=1S/C19H33N5O6/c20-9-3-1-2-8(4-9)6-24-7-12-15(26)16(27)13(23)19(29-12)30-18-11(22)5-10(21)14(25)17(18)28/h1-4,10-19,24-28H,5-7,20-23H2/t10-,11+,12-,13-,14+,15-,16-,17-,18-,19-/m1/s1

Standard InChI Key:  KMCWXKUEWLRGRM-ITRADPEYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
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   38.0580  -11.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.6676  -12.1871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3906  -12.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4182  -13.3966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7508  -10.8812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9153  -10.9767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.8079  -12.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.9687  -12.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2446  -12.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2245  -11.4088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5045  -11.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8031  -11.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8264  -12.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.5763  -13.4829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.0804  -11.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4823  -10.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2793  -13.0514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.1260  -12.6989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1829   -9.7695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1629   -8.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8604   -8.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5745   -8.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2715   -8.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2520   -7.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5295   -7.2841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8354   -7.7115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9888   -8.8843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  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
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 12 17  1  0
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 15 19  1  6
 14 20  1  1
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 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
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4443278

   ---

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: 427.50

Molecular Weight (Monoisotopic): 427.2431

AlogP: -3.70

#Rotatable Bonds: 6

Polar Surface Area: 215.49

Molecular Species: BASE

HBA: 11

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.66

CX Basic pKa: 9.15

CX LogP: -3.96

CX LogD: -7.89

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.20

Np Likeness Score: 0.86

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