ID: ALA2408225

Max Phase: Preclinical

Molecular Formula: C18H19N3O5

Molecular Weight: 357.37

Molecule Type: Small molecule

Representations

Canonical SMILES:  OC[C@H]1O[C@@H](c2nc(-c3ccc4ccccc4c3)n[nH]2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H19N3O5/c22-8-12-13(23)14(24)15(25)16(26-12)18-19-17(20-21-18)11-6-5-9-3-1-2-4-10(9)7-11/h1-7,12-16,22-25H,8H2,(H,19,20,21)/t12-,13-,14+,15-,16-/m1/s1

Standard InChI Key:  FJYFMJBUCUOYNH-IBEHDNSVSA-N

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

Properties

Molecular Weight: 357.37

Molecular Weight (Monoisotopic): 357.1325

AlogP: 0.14

#Rotatable Bonds: 3

Polar Surface Area: 131.72

Molecular Species: NEUTRAL

HBA: 7

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.48

CX Basic pKa: 0.50

CX LogP: 0.45

CX LogD: 0.44

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: 0.23

References

1. Bokor E, Docsa T, Gergely P, Somsák L..  (2013)  C-Glucopyranosyl-1,2,4-triazoles As New Potent Inhibitors of Glycogen Phosphorylase.,  4  (7): [PMID:24900719] [10.1021/ml4001529]

2. Kun S, Bokor É, Varga G, Szőcs B, Páhi A, Czifrák K, Tóth M, Juhász L, Docsa T, Gergely P, Somsák L..  (2014)  New synthesis of 3-(β-D-glucopyranosyl)-5-substituted-1,2,4-triazoles, nanomolar inhibitors of glycogen phosphorylase.,  76  [PMID:24608000] [10.1016/j.ejmech.2014.02.041]

3. 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]

4. Kyriakis E, Karra AG, Papaioannou O, Solovou T, Skamnaki VT, Liggri PGV, Zographos SE, Szennyes E, Bokor É, Kun S, Psarra AG, Somsák L, Leonidas DD..  (2020)  The architecture of hydrogen and sulfur σ-hole interactions explain differences in the inhibitory potency of C-β-d-glucopyranosyl thiazoles, imidazoles and an N-β-d glucopyranosyl tetrazole for human liver glycogen phosphorylase and offer new insights to structure-based design.,  28  (1): [PMID:31767404] [10.1016/j.bmc.2019.115196]

Source

Source(1):

• Scientific Literature