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

ID: ALA4583631

PubChem CID: 155561966

Max Phase: Preclinical

Molecular Formula: C14H30N4O6

Molecular Weight: 350.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCNC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](N)C[C@@H]2N)[C@H](N)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C14H30N4O6/c1-2-18-4-7-10(20)11(21)8(17)14(23-7)24-13-6(16)3-5(15)9(19)12(13)22/h5-14,18-22H,2-4,15-17H2,1H3/t5-,6+,7-,8-,9+,10-,11-,12-,13-,14-/m1/s1

Standard InChI Key:  LBZJOJFBCAVMHU-JPYLPOILSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    8.2499  -11.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2223  -10.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4996  -10.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042  -10.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8319  -11.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5548  -12.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5824  -13.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9151  -10.5015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0796  -10.5969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9721  -12.1420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1330  -12.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4089  -11.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3888  -11.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6688  -10.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9674  -11.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9907  -11.8872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7154  -12.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7406  -13.1032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447  -10.6760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6466   -9.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4436  -12.6676    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2903  -12.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3471   -9.3856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250   -8.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0255   -8.1370    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4583631

   ---

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: 350.42

Molecular Weight (Monoisotopic): 350.2165

AlogP: -4.46

#Rotatable Bonds: 5

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: 9.43

CX LogP: -4.50

CX LogD: -9.20

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.24

Np Likeness Score: 1.58

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