(2R,3S,4R,5R,6S)-5-amino-6-((1R,2R,3S,4R,6S)-4,6-diamino-2-((2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yloxy)-3-hydroxycyclohexyloxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

ID: ALA474967

PubChem CID: 16750529

Max Phase: Preclinical

Molecular Formula: C17H34N4O10

Molecular Weight: 454.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H34N4O10/c18-2-6-10(24)13(27)17(28-6)31-15-9(23)4(19)1-5(20)14(15)30-16-8(21)12(26)11(25)7(3-22)29-16/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1

Standard InChI Key:  FNBQIDOUCINBIA-VVPCINPTSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  1  0  0  0  0  0999 V2000
   -2.2708   -4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2708   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5588   -5.9833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8468   -5.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8468   -4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5588   -4.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9865   -4.3396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1329   -5.9885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9847   -5.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5588   -3.5083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311   -4.3396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998   -5.5771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -6.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8558   -7.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8590   -8.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1470   -8.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5699   -8.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5748   -7.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5678   -6.8054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513   -9.2860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -6.8129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2847   -7.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0321   -6.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879   -7.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797   -8.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3718   -8.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4078   -7.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5198   -8.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5756   -8.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -8.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7388   -6.6344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  1  2  1  0
 14 19  1  1
  2  9  1  6
 16 20  1  1
  1  6  1  0
 18 21  1  1
  6 10  1  6
 22 19  1  1
 22 23  1  0
  2  3  1  0
  5 11  1  1
  3  4  1  0
  9 12  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
  4  5  1  0
 24 27  1  1
 13  8  1  6
 25 28  1  6
 13 14  1  0
 15 29  1  6
  5  6  1  0
 26 30  1  6
 27 31  1  0
  1  7  1  1
  4  8  1  1
 13 18  1  0
 14 15  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA474967

   (2R,3S,4R,5R,6S)-5-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]oxy-3-hydroxycyclohexyl]oxy-2-(hydroxymethyl)oxane-3,4-diol;sulfuric acid

2. Parent:

   

   ALA474967

   (1r,2r,3s,4r,6s)-4,6-Diamino-2-[(5-Amino-5-Deoxy-Beta-D-Ribofuranosyl)oxy]-3-Hydroxycyclohexyl 2-Amino-2-Deoxy-Alpha-D-Glucopyranoside

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 454.48

Molecular Weight (Monoisotopic): 454.2275

AlogP: -6.65

#Rotatable Bonds: 6

Polar Surface Area: 262.38

Molecular Species: BASE

HBA: 14

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 14

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.17

CX Basic pKa: 9.59

CX LogP: -6.43

CX LogD: -11.28

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.18

Np Likeness Score: 1.50

References

1. Nudelman I, Rebibo-Sabbah A, Cherniavsky M, Belakhov V, Hainrichson M, Chen F, Schacht J, Pilch DS, Ben-Yosef T, Baasov T..  (2009)  Development of novel aminoglycoside (NB54) with reduced toxicity and enhanced suppression of disease-causing premature stop mutations.,  52  (9): [PMID:19309154] [10.1021/jm801640k]

2. Nudelman I, Glikin D, Smolkin B, Hainrichson M, Belakhov V, Baasov T..  (2010)  Repairing faulty genes by aminoglycosides: development of new derivatives of geneticin (G418) with enhanced suppression of diseases-causing nonsense mutations.,  18  (11): [PMID:20409719] [10.1016/j.bmc.2010.03.060]

Source

Source(1):

• Scientific Literature