(1R,2S,3r,4R,5S,6s)-6-[(1-Octyl-1H-1,2,3-triazol-4-yl)methylamino]cyclohexane-1,2,3,4,5-pentaol

ID: ALA1085392

PubChem CID: 46867661

Max Phase: Preclinical

Molecular Formula: C17H32N4O5

Molecular Weight: 372.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCn1cc(CN[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)nn1

Standard InChI:  InChI=1S/C17H32N4O5/c1-2-3-4-5-6-7-8-21-10-11(19-20-21)9-18-12-13(22)15(24)17(26)16(25)14(12)23/h10,12-18,22-26H,2-9H2,1H3/t12-,13-,14+,15+,16-,17-

Standard InChI Key:  GOWXONIFDQHALJ-ZDVFKUJDSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    4.5750    1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9990    0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9990    1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870    2.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8611    0.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7129    0.4490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8593    2.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2870   -0.3708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7147    2.0979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4280    1.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2075    1.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8850    1.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5445    1.9817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2721    2.7611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4463    2.7424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3694    1.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7730    1.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5980    1.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0016    0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8266    0.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2302   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0552   -0.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4588   -0.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13 14  1  0
 15 16  1  0
  6  7  1  1
  1  2  1  0
  2  8  1  1
  1  6  1  0
 14 15  2  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
  4  9  1  1
 16 19  1  0
  2  3  1  0
 19 20  1  0
  1 10  1  6
 20 21  1  0
  3  4  1  0
 21 22  1  0
  3 11  1  6
 22 23  1  0
  4  5  1  0
 23 24  1  0
  5 12  1  6
 24 25  1  0
  5  6  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085392

   (1R,2S,3r,4R,5S,6s)-6-[(1-Octyl-1H-1,2,3-triazol-4-yl)methylamino]cyclohexane-1,2,3,4,5-pentaol

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: 372.47

Molecular Weight (Monoisotopic): 372.2373

AlogP: -1.09

#Rotatable Bonds: 10

Polar Surface Area: 143.89

Molecular Species: NEUTRAL

HBA: 9

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.50

CX Basic pKa: 5.99

CX LogP: -0.50

CX LogD: -0.52

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.28

Np Likeness Score: -0.51

References

1. Díaz L, Bujons J, Casas J, Llebaria A, Delgado A..  (2010)  Click chemistry approach to new N-substituted aminocyclitols as potential pharmacological chaperones for Gaucher disease.,  53  (14): [PMID:20557054] [10.1021/jm100198t]

2. Díaz L, Casas J, Bujons J, Llebaria A, Delgado A..  (2011)  New glucocerebrosidase inhibitors by exploration of chemical diversity of N-substituted aminocyclitols using click chemistry and in situ screening.,  54  (7): [PMID:21370884] [10.1021/jm101204u]

Source

Source(1):

• Scientific Literature