1-(2'-Amino-2'-deoxy-beta-D-glucopyranosyl)-4-phenyl-1,2,3-triazole

ID: ALA4079900

PubChem CID: 137650341

Max Phase: Preclinical

Molecular Formula: C14H18N4O4

Molecular Weight: 306.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1n1cc(-c2ccccc2)nn1

Standard InChI:  InChI=1S/C14H18N4O4/c15-11-13(21)12(20)10(7-19)22-14(11)18-6-9(16-17-18)8-4-2-1-3-5-8/h1-6,10-14,19-21H,7,15H2/t10-,11-,12-,13-,14-/m1/s1

Standard InChI Key:  QKAHXPNAXCAZOH-DHGKCCLASA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   24.1036  -18.5904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1036  -20.2297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6832  -21.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2669  -20.2298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6831  -18.5904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6440  -19.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3975  -18.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3975  -19.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6831  -20.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9771  -19.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9771  -18.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2669  -18.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8467  -18.9245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3922  -18.3184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9844  -17.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1869  -17.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3167  -16.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1290  -16.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4612  -16.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9806  -15.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1640  -15.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8355  -16.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 12  1  0
 11  5  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
  7  1  1  1
  8  2  1  6
  9  3  1  1
 10  4  1  6
  1 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  1  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4079900

   ---

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: 306.32

Molecular Weight (Monoisotopic): 306.1328

AlogP: -1.12

#Rotatable Bonds: 3

Polar Surface Area: 126.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.91

CX Basic pKa: 8.31

CX LogP: -0.47

CX LogD: -1.42

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: 0.10

References

1. Bokor É, Kyriakis E, Solovou TGA, Koppány C, Kantsadi AL, Szabó KE, Szakács A, Stravodimos GA, Docsa T, Skamnaki VT, Zographos SE, Gergely P, Leonidas DD, Somsák L..  (2017)  Nanomolar Inhibitors of Glycogen Phosphorylase Based on β-d-Glucosaminyl Heterocycles: A Combined Synthetic, Enzyme Kinetic, and Protein Crystallography Study.,  60  (22): [PMID:28925695] [10.1021/acs.jmedchem.7b01056]

Source

Source(1):

• Scientific Literature