ID: ALA3351140

Max Phase: Preclinical

Molecular Formula: C13H17NO6

Molecular Weight: 283.28

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(N[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1ccccc1

Standard InChI:  InChI=1S/C13H17NO6/c15-6-8-9(16)10(17)11(18)13(20-8)14-12(19)7-4-2-1-3-5-7/h1-5,8-11,13,15-18H,6H2,(H,14,19)/t8-,9-,10+,11-,13+/m1/s1

Standard InChI Key:  SPYSOSUFGSNSMY-HMUNZLOLSA-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: 283.28

Molecular Weight (Monoisotopic): 283.1056

AlogP: -1.78

#Rotatable Bonds: 3

Polar Surface Area: 119.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.44

CX Basic pKa:

CX LogP: -1.37

CX LogD: -1.37

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.45

Np Likeness Score: 0.79

References

1. Pastor M, Cruciani G, Clementi S..  (1997)  Smart region definition: a new way to improve the predictive ability and interpretability of three-dimensional quantitative structure-activity relationships.,  40  (10): [PMID:9154968] [10.1021/jm9608016]

2. Venkatarangan P, Hopfinger AJ..  (1999)  Prediction of ligand-receptor binding thermodynamics by free energy force field three-dimensional quantitative structure-activity relationship analysis: applications to a set of glucose analogue inhibitors of glycogen phosphorylase.,  42  (12): [PMID:10377222] [10.1021/jm980515p]

3. Somsák L, Kovács L, Tóth M, Osz E, Szilágyi L, Györgydeák Z, Dinya Z, Docsa T, Tóth B, Gergely P..  (2001)  Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of d-gluco- and d-xylopyranosylidene-spiro-(thio)hydantoins and N-(d-glucopyranosyl) amides.,  44  (17): [PMID:11495595] [10.1021/jm010892t]

4. Pan D, Liu J, Senese C, Hopfinger AJ, Tseng Y..  (2004)  Characterization of a ligand-receptor binding event using receptor-dependent four-dimensional quantitative structure-activity relationship analysis.,  47  (12): [PMID:15163189] [10.1021/jm030586a]

5. Zamora I, Oprea T, Cruciani G, Pastor M, Ungell AL..  (2003)  Surface descriptors for protein-ligand affinity prediction.,  46  (1): [PMID:12502357] [10.1021/jm011051p]

6. Pastor M, Cruciani G, Watson KA..  (1997)  A strategy for the incorporation of water molecules present in a ligand binding site into a three-dimensional quantitative structure--activity relationship analysis.,  40  (25): [PMID:9406599] [10.1021/jm970273d]

7. Gohlke H, Klebe G..  (2002)  DrugScore meets CoMFA: adaptation of fields for molecular comparison (AFMoC) or how to tailor knowledge-based pair-potentials to a particular protein.,  45  (19): [PMID:12213058] [10.1021/jm020808p]

8. Somsák L, Nagy V, Vidal S, Czifrák K, Berzsényi E, Praly JP..  (2008)  Novel design principle validated: glucopyranosylidene-spiro-oxathiazole as new nanomolar inhibitor of glycogen phosphorylase, potential antidiabetic agent.,  18  (20): [PMID:18793852] [10.1016/j.bmcl.2008.08.052]

9. Tóth M, Kun S, Bokor E, Benltifa M, Tallec G, Vidal S, Docsa T, Gergely P, Somsák L, Praly JP..  (2009)  Synthesis and structure-activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase.,  17  (13): [PMID:19450985] [10.1016/j.bmc.2009.04.036]

10. Bokor E, Docsa T, Gergely P, Somsák L..  (2010)  Synthesis of 1-(D-glucopyranosyl)-1,2,3-triazoles and their evaluation as glycogen phosphorylase inhibitors.,  18  (3): [PMID:20080412] [10.1016/j.bmc.2009.12.043]

11. Nagy V, Felföldi N, Kónya B, Praly JP, Docsa T, Gergely P, Chrysina ED, Tiraidis C, Kosmopoulou MN, Alexacou KM, Konstantakaki M, Leonidas DD, Zographos SE, Oikonomakos NG, Kozmon S, Tvaroška I, Somsák L..  (2012)  N-(4-Substituted-benzoyl)-N'-(β-d-glucopyranosyl)ureas as inhibitors of glycogen phosphorylase: Synthesis and evaluation by kinetic, crystallographic, and molecular modelling methods.,  20  (5): [PMID:22325154] [10.1016/j.bmc.2011.12.059]

12. 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]

13. Polyák M, Varga G, Szilágyi B, Juhász L, Docsa T, Gergely P, Begum J, Hayes JM, Somsák L..  (2013)  Synthesis, enzyme kinetics and computational evaluation of N-(β-D-glucopyranosyl) oxadiazolecarboxamides as glycogen phosphorylase inhibitors.,  21  (18): [PMID:23938052] [10.1016/j.bmc.2013.07.024]

14. Uddin R, Saeed M, Ul-Haq Z.  (2013)  Molecular docking- and genetic algorithm-based approaches to produce robust 3D-QSAR models,  [10.1007/s00044-013-0812-0]

15. 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]

Source

Source(1):

• Scientific Literature