(1R,3S,6R)-4,6-Diamino-3-(4-methoxy-benzyloxy)-cyclohexane-1,2-diol

ID: ALA198549

PubChem CID: 44404599

Max Phase: Preclinical

Molecular Formula: C14H22N2O4

Molecular Weight: 282.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CO[C@H]2C(N)C[C@@H](N)[C@@H](O)C2O)cc1

Standard InChI:  InChI=1S/C14H22N2O4/c1-19-9-4-2-8(3-5-9)7-20-14-11(16)6-10(15)12(17)13(14)18/h2-5,10-14,17-18H,6-7,15-16H2,1H3/t10-,11?,12-,13?,14+/m1/s1

Standard InChI Key:  ROAPEGAALYTRSX-UKVZVYNXSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  1  0  0  0  0  0999 V2000
    2.4042   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -0.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -2.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -0.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -0.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250   -1.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500    0.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500    0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458    1.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583    1.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250    2.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  1  0
  2  7  1  1
  8  1  1  0
  9  4  1  0
  5 10  1  1
  3 11  1  6
 12  7  1  0
 13 12  1  0
 14 17  1  0
 15 13  2  0
 16 13  1  0
 17 16  2  0
 18 15  1  0
 19 14  1  0
 20 19  1  0
  6  4  1  0
 14 18  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA198549

   (1R,3S,6R)-4,6-diamino-3-[(4-methoxyphenyl)methoxy]cyclohexane-1,2-diol

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: 282.34

Molecular Weight (Monoisotopic): 282.1580

AlogP: -0.64

#Rotatable Bonds: 4

Polar Surface Area: 110.96

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.99

CX Basic pKa: 9.29

CX LogP: -1.10

CX LogD: -3.29

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.58

Np Likeness Score: 0.95

References

1. Wang X, Migawa MT, Sannes-Lowery KA, Swayze EE..  (2005)  The synthesis and 16S A-site rRNA recognition of carbohydrate-free aminoglycosides.,  15  (22): [PMID:16168642] [10.1016/j.bmcl.2005.08.027]

Source

Source(1):

• Scientific Literature