(1R,3S,6R)-4,6-Diamino-2-[2-(3-amino-propylamino)-ethoxy]-3-(4-methoxy-benzyloxy)-cyclohexanol

ID: ALA371080

PubChem CID: 44404604

Max Phase: Preclinical

Molecular Formula: C19H34N4O4

Molecular Weight: 382.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CO[C@H]2C(N)C[C@@H](N)[C@@H](O)C2OCCNCCCN)cc1

Standard InChI:  InChI=1S/C19H34N4O4/c1-25-14-5-3-13(4-6-14)12-27-18-16(22)11-15(21)17(24)19(18)26-10-9-23-8-2-7-20/h3-6,15-19,23-24H,2,7-12,20-22H2,1H3/t15-,16?,17-,18+,19?/m1/s1

Standard InChI Key:  RVAZIBMRUIDVRX-BXBVOISASA-N

Molfile:  

     RDKit          2D

 27 28  0  0  1  0  0  0  0  0999 V2000
    3.5542   -0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -0.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042    0.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -1.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167    0.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167   -0.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -1.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917    0.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1750    1.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -3.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0125   -3.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    0.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3083    0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000    1.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    2.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3000   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833    2.9208    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 19  1  0
 15 25  1  0
 16 24  1  0
 17 13  2  0
 18 13  1  0
 19 18  2  0
 20 17  1  0
 21 23  1  0
 22 14  1  0
 23 15  1  0
 24 21  1  0
 25 26  1  0
 26  8  1  0
 27 22  1  0
  6  4  1  0
 14 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA371080

   (1R,3S,6R)-4,6-diamino-2-[2-(3-aminopropylamino)ethoxy]-3-[(4-methoxyphenyl)methoxy]cyclohexan-1-ol

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: 382.51

Molecular Weight (Monoisotopic): 382.2580

AlogP: -0.68

#Rotatable Bonds: 11

Polar Surface Area: 138.01

Molecular Species: BASE

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.53

CX Basic pKa: 10.17

CX LogP: -1.55

CX LogD: -7.60

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.32

Np Likeness Score: 0.60

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