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

ID: ALA4517375

PubChem CID: 155540926

Max Phase: Preclinical

Molecular Formula: C21H36N4O8

Molecular Weight: 472.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1cccc(CNC[C@H]2O[C@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](N)C[C@@H]3N)[C@H](N)[C@@H](O)[C@@H]2O)c1O

Standard InChI:  InChI=1S/C21H36N4O8/c1-2-31-12-5-3-4-9(15(12)26)7-25-8-13-17(28)18(29)14(24)21(32-13)33-20-11(23)6-10(22)16(27)19(20)30/h3-5,10-11,13-14,16-21,25-30H,2,6-8,22-24H2,1H3/t10-,11+,13-,14-,16+,17-,18-,19-,20-,21-/m1/s1

Standard InChI Key:  KFLORLMSCDDOAD-DMMKYTHCSA-N

Molfile:  

 
     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   37.7472   -5.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7196   -4.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9969   -3.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3015   -4.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3292   -5.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0521   -5.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0798   -6.4464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.4124   -3.9309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5769   -4.0264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4694   -5.5715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6303   -5.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9062   -5.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8861   -4.4586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1661   -4.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4647   -4.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4880   -5.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2127   -5.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2379   -6.5327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7420   -4.1054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1439   -3.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9409   -6.1012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.7876   -5.7486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8444   -2.8192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.8244   -2.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5219   -1.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2397   -1.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9367   -1.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9171   -0.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1947   -0.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5006   -0.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2587   -2.7866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.6540   -1.9360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3517   -1.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0690   -1.9021    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
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 26 31  1  0
 27 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4517375

   ---

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: 472.54

Molecular Weight (Monoisotopic): 472.2533

AlogP: -3.18

#Rotatable Bonds: 8

Polar Surface Area: 218.93

Molecular Species: BASE

HBA: 12

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.18

CX Basic pKa: 8.86

CX LogP: -4.14

CX LogD: -7.37

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.18

Np Likeness Score: 0.84

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