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

ID: ALA4531748

PubChem CID: 155546548

Max Phase: Preclinical

Molecular Formula: C19H31ClN4O6

Molecular Weight: 446.93

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](CNCc2ccccc2Cl)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H31ClN4O6/c20-9-4-2-1-3-8(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,5-7,21-23H2/t10-,11+,12-,13-,14+,15-,16-,17-,18-,19-/m1/s1

Standard InChI Key:  ZGCRPSVWSGGOON-ITRADPEYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   28.1968  -12.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1691  -11.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4465  -11.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7511  -11.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7788  -12.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5017  -12.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5293  -13.6030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8620  -11.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0265  -11.1830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9190  -12.7281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0799  -12.8237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3558  -12.4372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3357  -11.6152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6156  -11.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9143  -11.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9376  -12.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6622  -12.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6875  -13.6893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1916  -11.2620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5935  -10.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3905  -13.2578    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.2372  -12.9053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2940   -9.9758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2740   -9.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9715   -8.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6857   -9.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3827   -8.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3631   -7.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6407   -7.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9466   -7.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7047   -9.9412    0.0000 Cl  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
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4531748

   ---

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: 446.93

Molecular Weight (Monoisotopic): 446.1932

AlogP: -2.63

#Rotatable Bonds: 6

Polar Surface Area: 189.47

Molecular Species: BASE

HBA: 10

HBD: 8

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.66

CX Basic pKa: 9.15

CX LogP: -2.53

CX LogD: -5.92

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.23

Np Likeness Score: 0.66

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