(2S,3R,4S,5S,6R)-2-(2-(4-methoxybenzyl)phenoxy)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

ID: ALA270766

Chembl Id: CHEMBL270766

Cas Number: 360775-96-8

PubChem CID: 10177526

Max Phase: Preclinical

Molecular Formula: C20H24O7

Molecular Weight: 376.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(Cc2ccccc2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C20H24O7/c1-25-14-8-6-12(7-9-14)10-13-4-2-3-5-15(13)26-20-19(24)18(23)17(22)16(11-21)27-20/h2-9,16-24H,10-11H2,1H3/t16-,17-,18+,19-,20-/m1/s1

Standard InChI Key:  HFLCZNNDZKKXCS-OUUBHVDSSA-N

Alternative Forms

1. Parent:

   

   ALA270766

   SERGLIFLOZIN A

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: 376.41

Molecular Weight (Monoisotopic): 376.1522

AlogP: 0.46

#Rotatable Bonds: 6

Polar Surface Area: 108.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: 1.34

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 1.08

References

1. Meng W, Ellsworth BA, Nirschl AA, McCann PJ, Patel M, Girotra RN, Wu G, Sher PM, Morrison EP, Biller SA, Zahler R, Deshpande PP, Pullockaran A, Hagan DL, Morgan N, Taylor JR, Obermeier MT, Humphreys WG, Khanna A, Discenza L, Robertson JG, Wang A, Han S, Wetterau JR, Janovitz EB, Flint OP, Whaley JM, Washburn WN..  (2008)  Discovery of dapagliflozin: a potent, selective renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.,  51  (5): [PMID:18260618] [10.1021/jm701272q]

2. Washburn WN..  (2009)  Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.,  52  (7): [PMID:19243175] [10.1021/jm8013019]

3. Lee J, Lee SH, Seo HJ, Son EJ, Lee SH, Jung ME, Lee M, Han HK, Kim J, Kang J, Lee J..  (2010)  Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: 1,3,4-Thiadiazolylmethylphenyl glucoside congeners.,  18  (6): [PMID:20181486] [10.1016/j.bmc.2010.01.073]

4. Ohtake Y, Sato T, Matsuoka H, Nishimoto M, Taka N, Takano K, Yamamoto K, Ohmori M, Higuchi T, Murakata M, Kobayashi T, Morikawa K, Shimma N, Suzuki M, Hagita H, Ozawa K, Yamaguchi K, Kato M, Ikeda S..  (2011)  5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.,  19  (18): [PMID:21873071] [10.1016/j.bmc.2011.08.005]

5. Ohtake Y, Sato T, Matsuoka H, Kobayashi T, Nishimoto M, Taka N, Takano K, Yamamoto K, Ohmori M, Higuchi T, Murakata M, Morikawa K, Shimma N, Suzuki M, Hagita H, Ozawa K, Yamaguchi K, Kato M, Ikeda S..  (2012)  C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.,  20  (13): [PMID:22652255] [10.1016/j.bmc.2012.04.053]

6. Cao X, Zhang W, Yan X, Huang Z, Zhang Z, Wang P, Shen J..  (2016)  Modification on the O-glucoside of Sergliflozin-A: A new strategy for SGLT2 inhibitor design.,  26  (9): [PMID:27025345] [10.1016/j.bmcl.2016.03.065]

7. Romero FA, Jones CT, Xu Y, Fenaux M, Halcomb RL..  (2020)  The Race to Bash NASH: Emerging Targets and Drug Development in a Complex Liver Disease.,  63  (10): [PMID:31930920] [10.1021/acs.jmedchem.9b01701]

8. Liu C, Han J, Marcelina O, Nugrahaningrum DA, Huang S, Zou M, Wang G, Miyagishi M, He Y, Wu S, Kasim V..  (2022)  Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia.,  65  (1.0): [PMID:34939794] [10.1021/acs.jmedchem.1c00947]

9. Maccari R, Ottanà R..  (2022)  Sodium-Glucose Cotransporter Inhibitors as Antidiabetic Drugs: Current Development and Future Perspectives.,  65  (16.0): [PMID:35924548] [10.1021/acs.jmedchem.2c00867]

Source

Source(1):

• Scientific Literature