5-[4'-Carboxy-(1,1'-biphenyl)-4-yl]-3-(beta-D-glucopyranosyl)-1,2,4-triazole

ID: ALA4172670

PubChem CID: 132281931

Max Phase: Preclinical

Molecular Formula: C21H21N3O7

Molecular Weight: 427.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(-c2ccc(-c3n[nH]c([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)n3)cc2)cc1

Standard InChI:  InChI=1S/C21H21N3O7/c25-9-14-15(26)16(27)17(28)18(31-14)20-22-19(23-24-20)12-5-1-10(2-6-12)11-3-7-13(8-4-11)21(29)30/h1-8,14-18,25-28H,9H2,(H,29,30)(H,22,23,24)/t14-,15-,16+,17-,18-/m1/s1

Standard InChI Key:  UQZVJUDMJCTDEV-UYTYNIKBSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    5.6073   -9.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8982  -10.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8982  -11.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6073  -11.5439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891  -11.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891  -12.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4800  -11.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751  -11.5439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4800  -10.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1891   -9.9136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -9.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -9.0964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3539  -10.2377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020   -9.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4934   -8.9208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6928   -9.0904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7123   -9.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0433  -10.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8552  -10.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3369   -9.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0011   -9.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1902   -9.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1461   -9.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4781  -10.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2901  -10.8058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7709  -10.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4341   -9.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6231   -9.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5857  -10.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9194  -10.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0648   -9.5643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
  9 11  1  1
 11 12  1  0
  2 10  1  0
  1 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16  1  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
 14 17  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 20 23  1  0
 29 30  1  0
 29 31  2  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4172670

   ---

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: 427.41

Molecular Weight (Monoisotopic): 427.1380

AlogP: 0.35

#Rotatable Bonds: 5

Polar Surface Area: 169.02

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.06

CX Basic pKa: 0.51

CX LogP: 0.68

CX LogD: -2.47

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.34

Np Likeness Score: 0.19

References

1. Kun S, Begum J, Kyriakis E, Stamati ECV, Barkas TA, Szennyes E, Bokor É, Szabó KE, Stravodimos GA, Sipos Á, Docsa T, Gergely P, Moffatt C, Patraskaki MS, Kokolaki MC, Gkerdi A, Skamnaki VT, Leonidas DD, Somsák L, Hayes JM..  (2018)  A multidisciplinary study of 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazole derivatives as glycogen phosphorylase inhibitors: Computation, synthesis, crystallography and kinetics reveal new potent inhibitors.,  147  [PMID:29453094] [10.1016/j.ejmech.2018.01.095]

Source

Source(1):

• Scientific Literature