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

ID: ALA4585318

PubChem CID: 155562398

Max Phase: Preclinical

Molecular Formula: C17H34N4O6

Molecular Weight: 390.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C(\C)CNC[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/C17H34N4O6/c1-3-7(2)5-21-6-10-13(23)14(24)11(20)17(26-10)27-16-9(19)4-8(18)12(22)15(16)25/h3,8-17,21-25H,4-6,18-20H2,1-2H3/b7-3+/t8-,9+,10-,11-,12+,13-,14-,15-,16-,17-/m1/s1

Standard InChI Key:  DHAHKRZBHCUBKF-WVOVYOKDSA-N

Molfile:  

 
     RDKit          2D

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   18.2374   -4.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2097   -3.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4837   -2.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7852   -3.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8130   -4.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5392   -4.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5670   -5.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9057   -2.8956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0573   -2.9957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9630   -4.5478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1109   -4.6438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3835   -4.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3633   -3.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6401   -3.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9355   -3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9589   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6869   -4.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7122   -5.5133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2096   -3.0751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6179   -2.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4184   -5.0758    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2554   -4.7257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3215   -1.7789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2992   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0029   -0.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9807    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7289   -0.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6844    0.7338    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  2  0
 25 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4585318

   ---

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: 390.48

Molecular Weight (Monoisotopic): 390.2478

AlogP: -3.52

#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: -3.50

CX LogD: -7.75

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.21

Np Likeness Score: 1.75

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