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

ID: ALA1082596

PubChem CID: 46867529

Max Phase: Preclinical

Molecular Formula: C19H36N4O5

Molecular Weight: 400.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCn1cc(CN[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)nn1

Standard InChI:  InChI=1S/C19H36N4O5/c1-2-3-4-5-6-7-8-9-10-23-12-13(21-22-23)11-20-14-15(24)17(26)19(28)18(27)16(14)25/h12,14-20,24-28H,2-11H2,1H3/t14-,15-,16+,17+,18-,19-

Standard InChI Key:  DCJWZIGHKBTFDW-OXHPVDPFSA-N

Molfile:  

     RDKit          2D

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    6.6042   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6042   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3162   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0282   -3.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0282   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3162   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3162   -1.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8903   -3.9177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7421   -3.9177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8885   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3162   -4.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7439   -2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4571   -2.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2366   -2.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9142   -2.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5736   -2.3849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3012   -1.6056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4755   -1.6243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3986   -2.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8022   -3.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6272   -3.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0308   -3.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8557   -3.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2594   -4.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0843   -4.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4880   -5.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3129   -5.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7166   -6.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 12 13  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1082596

   (1R,2S,3r,4R,5S,6s)-6-[(1-Decyl-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: 400.52

Molecular Weight (Monoisotopic): 400.2686

AlogP: -0.30

#Rotatable Bonds: 12

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: 0.39

CX LogD: 0.37

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.26

Np Likeness Score: -0.47

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