alpha-D-glucopyranosyl-1H-1,2,3-triazole

ID: ALA1169832

PubChem CID: 49798492

Max Phase: Preclinical

Molecular Formula: C8H13N3O5

Molecular Weight: 231.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@H](n2ccnn2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C8H13N3O5/c12-3-4-5(13)6(14)7(15)8(16-4)11-2-1-9-10-11/h1-2,4-8,12-15H,3H2/t4-,5-,6+,7-,8+/m1/s1

Standard InChI Key:  KSCJUOAWXPNFKK-CBQIKETKSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    1.1333    0.7415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196    1.5620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0265    1.7335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4390    1.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870    0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4189   -0.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1333   -0.9085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956   -0.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956   -1.7335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0101   -0.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7246   -0.9085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0101    0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2956    0.7415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7246    0.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4390    0.3290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 13 15  1  1
 15 16  1  0
  6 14  1  0
  6  1  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1169832

   (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(triazol-1-yl)oxane-3,4,5-triol

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: 231.21

Molecular Weight (Monoisotopic): 231.0855

AlogP: -2.75

#Rotatable Bonds: 2

Polar Surface Area: 120.86

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.33

CX Basic pKa: 0.61

CX LogP: -2.39

CX LogD: -2.39

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.44

Np Likeness Score: 0.88

References

1. Slámová K, Marhol P, Bezouska K, Lindkvist L, Hansen SG, Kren V, Jensen HH..  (2010)  Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles.,  20  (14): [PMID:20542427] [10.1016/j.bmcl.2010.04.151]

Source

Source(1):

• Scientific Literature