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

ID: ALA1766482

PubChem CID: 52937714

Max Phase: Preclinical

Molecular Formula: C20H38N4O5

Molecular Weight: 414.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCn1cc(CN[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)nn1

Standard InChI:  InChI=1S/C20H38N4O5/c1-2-3-4-5-6-7-8-9-10-11-24-13-14(22-23-24)12-21-15-16(25)18(27)20(29)19(28)17(15)26/h13,15-21,25-29H,2-12H2,1H3/t15-,16-,17+,18+,19-,20-

Standard InChI Key:  YKRCVGFYAOXFRY-VYEXIYEWSA-N

Molfile:  

     RDKit          2D

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   14.6125  -29.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3245  -29.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0365  -29.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0365  -28.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3245  -27.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3245  -27.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7504  -29.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8986  -29.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7522  -27.8854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8968  -27.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3245  -30.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4655  -28.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1811  -27.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9309  -28.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4847  -27.6170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0743  -26.9013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2669  -27.0706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3049  -27.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7918  -27.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6120  -27.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0989  -26.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9191  -26.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4060  -25.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2262  -25.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7131  -25.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5333  -25.3962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0202  -24.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8404  -24.8188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
  6  7  1  1
  1  2  1  0
  4  8  1  1
  1  6  1  0
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 16 17  1  0
 17 18  2  0
 18 14  1  0
  2  9  1  1
 16 19  1  0
  2  3  1  0
 19 20  1  0
  5 10  1  6
 20 21  1  0
  3  4  1  0
 21 22  1  0
  1 11  1  6
 22 23  1  0
  4  5  1  0
 23 24  1  0
  3 12  1  6
 24 25  1  0
  5  6  1  0
 25 26  1  0
 10 13  1  0
 26 27  1  0
 27 28  1  0
 13 14  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1766482

   rel-(1R,2S,4R,5S)-6-[[1-Undecyl-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: 414.55

Molecular Weight (Monoisotopic): 414.2842

AlogP: 0.09

#Rotatable Bonds: 13

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: 0.83

CX LogD: 0.82

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.25

Np Likeness Score: -0.46

References

1. 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