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

ID: ALA4435966

PubChem CID: 155511454

Max Phase: Preclinical

Molecular Formula: C19H38N4O6

Molecular Weight: 418.54

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](CNCC2CCCCC2)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C19H38N4O6/c20-10-6-11(21)18(17(27)14(10)24)29-19-13(22)16(26)15(25)12(28-19)8-23-7-9-4-2-1-3-5-9/h9-19,23-27H,1-8,20-22H2/t10-,11+,12-,13-,14+,15-,16-,17-,18-,19-/m1/s1

Standard InChI Key:  WRSRQWXJXDEGQF-ITRADPEYSA-N

Molfile:  

 
     RDKit          2D

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    8.0022  -18.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9746  -18.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2519  -17.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5566  -18.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5842  -19.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3072  -19.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3348  -20.2354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6675  -17.7159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8319  -17.8155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7245  -19.3606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8854  -19.4562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612  -19.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412  -18.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211  -17.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7197  -18.2838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7430  -19.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4677  -19.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930  -20.3217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9971  -17.8945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3990  -17.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1959  -19.8861    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427  -19.5377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995  -16.6041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0773  -15.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7778  -15.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984  -15.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1969  -15.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1790  -14.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4564  -14.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7518  -14.5344    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
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4435966

   ---

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: 418.54

Molecular Weight (Monoisotopic): 418.2791

AlogP: -2.90

#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: 9.68

CX LogP: -2.74

CX LogD: -7.83

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.22

Np Likeness Score: 1.19

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