(1R,3S,6R)-4,6-Diamino-3-(7-trifluoromethyl-quinolin-4-ylsulfanylmethoxy)-cyclohexane-1,2-diol

ID: ALA197808

PubChem CID: 44404591

Max Phase: Preclinical

Molecular Formula: C17H20F3N3O3S

Molecular Weight: 403.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC1C[C@@H](N)[C@@H](O)C(O)[C@H]1OCSc1ccnc2cc(C(F)(F)F)ccc12

Standard InChI:  InChI=1S/C17H20F3N3O3S/c18-17(19,20)8-1-2-9-12(5-8)23-4-3-13(9)27-7-26-16-11(22)6-10(21)14(24)15(16)25/h1-5,10-11,14-16,24-25H,6-7,21-22H2/t10-,11?,14-,15?,16+/m1/s1

Standard InChI Key:  IAWDEFIJAIUNGM-NFBVCUJYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  1  0  0  0  0  0999 V2000
    3.6667   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -1.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1708    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2125   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5208    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -1.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -1.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    0.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833    0.2625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6583    1.5583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208    1.4250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -1.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2042   -0.7917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -3.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -1.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -0.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -2.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4333   -2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3375   -1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 10  1  0
  4  1  1  0
  5  2  1  0
  6  4  1  0
  7 14  1  0
  8  6  1  0
  9  7  1  0
 10 15  2  0
 11  9  2  0
 12  7  2  0
 13 26  2  0
 14 21  1  0
 15 12  1  0
 16 20  1  0
 17  3  1  0
 18  3  1  0
 19  3  1  0
  4 20  1  1
 21 16  1  0
 22  1  1  0
  5 23  1  1
 24  6  1  0
  2 25  1  6
 26 27  1  0
 27 14  2  0
  5  8  1  0
 13  9  1  0
 10 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA197808

   (1R,3S,6R)-4,6-diamino-3-[[7-(trifluoromethyl)quinolin-4-yl]sulfanylmethoxy]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: 403.43

Molecular Weight (Monoisotopic): 403.1177

AlogP: 1.47

#Rotatable Bonds: 4

Polar Surface Area: 114.62

Molecular Species: BASE

HBA: 7

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: 0.45

CX LogD: -1.75

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -0.16

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