(5R,7R,8R,9S,10R)-7-(Hydroxymethyl)-3-(2-naphthyl)-1,6-dioxa-2-azaspiro[4,5]dec-2-ene-8,9,10-triol

ID: ALA594021

Chembl Id: CHEMBL594021

PubChem CID: 44263485

Max Phase: Preclinical

Molecular Formula: C18H19NO6

Molecular Weight: 345.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@]2(CC(c3ccc4ccccc4c3)=NO2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H19NO6/c20-9-14-15(21)16(22)17(23)18(24-14)8-13(19-25-18)12-6-5-10-3-1-2-4-11(10)7-12/h1-7,14-17,20-23H,8-9H2/t14-,15-,16+,17-,18-/m1/s1

Standard InChI Key:  YKACTKXMYNIMHP-UYTYNIKBSA-N

Alternative Forms

1. Parent:

   

   ALA594021

   Glucopyranosylidene-spiro-isoxazoline, 4e

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: 345.35

Molecular Weight (Monoisotopic): 345.1212

AlogP: 0.13

#Rotatable Bonds: 2

Polar Surface Area: 111.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.05

CX Basic pKa: 2.59

CX LogP: 0.67

CX LogD: 0.67

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: 1.28

References

1. Benltifa M, Hayes JM, Vidal S, Gueyrard D, Goekjian PG, Praly JP, Kizilis G, Tiraidis C, Alexacou KM, Chrysina ED, Zographos SE, Leonidas DD, Archontis G, Oikonomakos NG..  (2009)  Glucose-based spiro-isoxazolines: a new family of potent glycogen phosphorylase inhibitors.,  17  (20): [PMID:19781947] [10.1016/j.bmc.2009.08.060]

2. Krimm I, Lancelin JM, Praly JP..  (2012)  Binding evaluation of fragment-based scaffolds for probing allosteric enzymes.,  55  (3): [PMID:22229710] [10.1021/jm201439b]

3. Goyard D, Kónya B, Chajistamatiou AS, Chrysina ED, Leroy J, Balzarin S, Tournier M, Tousch D, Petit P, Duret C, Maurel P, Somsák L, Docsa T, Gergely P, Praly JP, Azay-Milhau J, Vidal S..  (2016)  Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition.,  108  [PMID:26708111] [10.1016/j.ejmech.2015.12.004]

4. Szabó KE, Kyriakis E, Psarra AG, Karra AG, Sipos Á, Docsa T, Stravodimos GA, Katsidou E, Skamnaki VT, Liggri PGV, Zographos SE, Mándi A, Király SB, Kurtán T, Leonidas DD, Somsák L..  (2019)  Glucopyranosylidene-spiro-imidazolinones, a New Ring System: Synthesis and Evaluation as Glycogen Phosphorylase Inhibitors by Enzyme Kinetics and X-ray Crystallography.,  62  (13): [PMID:31251604] [10.1021/acs.jmedchem.9b00356]

Source

Source(1):

• Scientific Literature