rel-(1R,2S,4R,5S)-6-[[1-(10-Hydroxydecyl)-1H-1,2,3-triazol-4-yl]methylamino]cyclohexane-1,2,3,4,5-pentaol

ID: ALA1766489

PubChem CID: 52937817

Max Phase: Preclinical

Molecular Formula: C19H36N4O6

Molecular Weight: 416.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCCCCCCCCCCn1cc(CN[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]2O)nn1

Standard InChI:  InChI=1S/C19H36N4O6/c24-10-8-6-4-2-1-3-5-7-9-23-12-13(21-22-23)11-20-14-15(25)17(27)19(29)18(28)16(14)26/h12,14-20,24-29H,1-11H2/t14-,15-,16+,17+,18-,19-

Standard InChI Key:  JZEYDOMKWQQKCY-OXHPVDPFSA-N

Molfile:  

     RDKit          2D

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   -3.2708  -21.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5588  -22.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8468  -21.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8468  -21.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5588  -20.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5588  -19.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1329  -22.2802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9847  -22.2802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311  -20.6313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9865  -20.6313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5588  -23.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4179  -21.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2978  -20.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0475  -20.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6014  -20.3629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1909  -19.6472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3835  -19.8164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4216  -20.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9085  -19.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7287  -19.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2156  -19.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0358  -19.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227  -18.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3429  -18.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8298  -18.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6500  -18.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1369  -17.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9571  -17.5646    0.0000 O   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
 15 16  1  0
 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:

   

   ALA1766489

   rel-(1R,2S,4R,5S)-6-[[1-(10-Hydroxydecyl)-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: 416.52

Molecular Weight (Monoisotopic): 416.2635

AlogP: -1.33

#Rotatable Bonds: 13

Polar Surface Area: 164.12

Molecular Species: NEUTRAL

HBA: 10

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.50

CX Basic pKa: 5.99

CX LogP: -1.05

CX LogD: -1.07

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.19

Np Likeness Score: -0.36

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