(2S,3R,4R,5S)-2-[4-Chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol

ID: ALA569434

Chembl Id: CHEMBL569434

PubChem CID: 24764501

Max Phase: Preclinical

Molecular Formula: C21H25ClO6

Molecular Weight: 408.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(Cc2cc([C@@H]3OC(OC)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)cc1

Standard InChI:  InChI=1S/C21H25ClO6/c1-3-27-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(26-2)28-20/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21?/m1/s1

Standard InChI Key:  XEEROTCYZVZEEI-AUGMSIGLSA-N

Alternative Forms

1. Parent:

   

   ALA569434

   (2S,3R,4R,5S)-2-[4-Chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methoxy-tetrahydro-pyran-3,4,5-triol

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: 408.88

Molecular Weight (Monoisotopic): 408.1340

AlogP: 2.46

#Rotatable Bonds: 6

Polar Surface Area: 88.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.21

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.68

Np Likeness Score: 0.58

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]

2. 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]

3. 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]

4. 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

Source(1):

• Scientific Literature