(2S,3R,4R,5S)-2-(3-(4-Ethoxybenzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

ID: ALA568398

Chembl Id: CHEMBL568398

PubChem CID: 24831388

Max Phase: Preclinical

Molecular Formula: C21H26O6

Molecular Weight: 374.43

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CCOc1ccc(Cc2cccc([C@@H]3OC(OC)[C@@H](O)[C@H](O)[C@H]3O)c2)cc1

Standard InChI:  InChI=1S/C21H26O6/c1-3-26-16-9-7-13(8-10-16)11-14-5-4-6-15(12-14)20-18(23)17(22)19(24)21(25-2)27-20/h4-10,12,17-24H,3,11H2,1-2H3/t17-,18-,19+,20+,21?/m1/s1

Standard InChI Key:  HUUIJUQVHFPDNW-AUGMSIGLSA-N

Associated Targets(Human)

SLC5A2 Tclin Sodium/glucose cotransporter 2 (2000 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Slc5a2 Sodium/glucose cotransporter 2 (38 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 374.43Molecular Weight (Monoisotopic): 374.1729AlogP: 1.80#Rotatable Bonds: 6
Polar Surface Area: 88.38Molecular Species: NEUTRALHBA: 6HBD: 3
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 12.21CX Basic pKa: CX LogP: 2.42CX LogD: 2.42
Aromatic Rings: 2Heavy Atoms: 27QED Weighted: 0.71Np Likeness Score: 0.91

References

1. Goodwin NC, Mabon R, Harrison BA, Shadoan MK, Almstead ZY, Xie Y, Healy J, Buhring LM, DaCosta CM, Bardenhagen J, Mseeh F, Liu Q, Nouraldeen A, Wilson AG, Kimball SD, Powell DR, Rawlins DB..  (2009)  Novel L-xylose derivatives as selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.,  52  (20): [PMID:19785435] [10.1021/jm900951n]

Source