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

ID: ALA4539971

PubChem CID: 155549837

Max Phase: Preclinical

Molecular Formula: C19H32N4O6

Molecular Weight: 412.49

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/C19H32N4O6/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/h1-5,10-19,23-27H,6-8,20-22H2/t10-,11+,12-,13-,14+,15-,16-,17-,18-,19-/m1/s1

Standard InChI Key:  BELYHEUEHQUUGN-ITRADPEYSA-N

Molfile:  

 
     RDKit          2D

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   28.5723   -5.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5447   -4.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8220   -3.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1267   -4.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1543   -5.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8773   -5.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9049   -6.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2376   -3.8979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4020   -3.9934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2946   -5.5385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4555   -5.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7313   -5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7113   -4.4255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9912   -4.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2898   -4.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3131   -5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0378   -5.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0631   -6.4996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5672   -4.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9691   -3.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7660   -6.0682    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.6128   -5.7156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6696   -2.7862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6496   -1.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3471   -1.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0649   -1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7619   -1.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7423   -0.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0199   -0.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3258   -0.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  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
M  END

Alternative Forms

1. Parent:

   

   ALA4539971

   ---

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: 412.49

Molecular Weight (Monoisotopic): 412.2322

AlogP: -3.28

#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: -3.13

CX LogD: -7.02

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.24

Np Likeness Score: 0.99

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