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

ID: ALA1766474

PubChem CID: 52937610

Max Phase: Preclinical

Molecular Formula: C19H34N4O5

Molecular Weight: 398.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@@H]1[C@@H](O)[C@H](O)[C@@H](NCc2cn(CCCCC3CCCCC3)nn2)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C19H34N4O5/c24-15-14(16(25)18(27)19(28)17(15)26)20-10-13-11-23(22-21-13)9-5-4-8-12-6-2-1-3-7-12/h11-12,14-20,24-28H,1-10H2/t14-,15-,16+,17+,18-,19-

Standard InChI Key:  SCLOQUUDNGPMRM-OXHPVDPFSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    4.6000  -10.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000  -11.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120  -11.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0240  -11.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0240  -10.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120   -9.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120   -9.1708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7379  -11.6510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8861  -11.6510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7397  -10.0021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843  -10.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120  -12.4708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4530  -10.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1686  -10.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9184  -10.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4722   -9.7337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0618   -9.0180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2544   -9.1873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2924   -9.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7793   -9.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5995   -9.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0864   -8.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9066   -8.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2357   -9.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0521   -9.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5426   -8.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2107   -8.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3883   -8.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  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
 23 24  1  0
  4  5  1  0
  3 12  1  6
  5  6  1  0
 10 13  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1766474

   rel-(1R,2S,4R,5S)-6-[[1-(4-Cyclohexylbutyl)-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: 398.50

Molecular Weight (Monoisotopic): 398.2529

AlogP: -0.69

#Rotatable Bonds: 8

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: -0.23

CX LogD: -0.25

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: -0.44

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