3-Benzofuran-5-yl-1-[2-hydroxy-4-methyl-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propan-1-one

ID: ALA183937

Chembl Id: CHEMBL183937

Cas Number: 209746-56-5

PubChem CID: 6918439

Max Phase: Preclinical

Molecular Formula: C24H26O9

Molecular Weight: 458.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c(C(=O)CCc2ccc3occc3c2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1

Standard InChI:  InChI=1S/C24H26O9/c1-12-8-16(27)20(15(26)4-2-13-3-5-17-14(10-13)6-7-31-17)18(9-12)32-24-23(30)22(29)21(28)19(11-25)33-24/h3,5-10,19,21-25,27-30H,2,4,11H2,1H3/t19-,21-,22+,23-,24-/m1/s1

Standard InChI Key:  GMYFQAHYWIYNES-PFKOEMKTSA-N

Alternative Forms

1. Parent:

   

   ALA183937

   T-1095A

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: 458.46

Molecular Weight (Monoisotopic): 458.1577

AlogP: 1.44

#Rotatable Bonds: 7

Polar Surface Area: 149.82

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.25

CX Basic pKa: ┄

CX LogP: 2.26

CX LogD: 2.25

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 1.56

References

1. Tsujihara K, Hongu M, Saito K, Kawanishi H, Kuriyama K, Matsumoto M, Oku A, Ueta K, Tsuda M, Saito A..  (1999)  Na(+)-glucose cotransporter (SGLT) inhibitors as antidiabetic agents. 4. Synthesis and pharmacological properties of 4'-dehydroxyphlorizin derivatives substituted on the B ring.,  42  (26): [PMID:10639275] [10.1021/jm990175n]

2. Dudash J, Zhang X, Zeck RE, Johnson SG, Cox GG, Conway BR, Rybczynski PJ, Demarest KT..  (2004)  Glycosylated dihydrochalcones as potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitors.,  14  (20): [PMID:15380212] [10.1016/j.bmcl.2004.07.082]

3. Zhang X, Urbanski M, Patel M, Zeck RE, Cox GG, Bian H, Conway BR, Pat Beavers M, Rybczynski PJ, Demarest KT..  (2005)  Heteroaryl-O-glucosides as novel sodium glucose co-transporter 2 inhibitors. Part 1.,  15  (23): [PMID:16198559] [10.1016/j.bmcl.2005.08.067]

4. Zhang X, Urbanski M, Patel M, Cox GG, Zeck RE, Bian H, Conway BR, Beavers MP, Rybczynski PJ, Demarest KT..  (2006)  Indole-glucosides as novel sodium glucose co-transporter 2 (SGLT2) inhibitors. Part 2.,  16  (6): [PMID:16380256] [10.1016/j.bmcl.2005.12.006]

5. 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]

6. Ellsworth BA, Meng W, Patel M, Girotra RN, Wu G, Sher PM, Hagan DL, Obermeier MT, Humphreys WG, Robertson JG, Wang A, Han S, Waldron TL, Morgan NN, Whaley JM, Washburn WN..  (2008)  Aglycone exploration of C-arylglucoside inhibitors of renal sodium-dependent glucose transporter SGLT2.,  18  (17): [PMID:18707880] [10.1016/j.bmcl.2008.07.109]

7. 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]

8. Nomura S, Sakamaki S, Hongu M, Kawanishi E, Koga Y, Sakamoto T, Yamamoto Y, Ueta K, Kimata H, Nakayama K, Tsuda-Tsukimoto M..  (2010)  Discovery of canagliflozin, a novel C-glucoside with thiophene ring, as sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes mellitus.,  53  (17): [PMID:20690635] [10.1021/jm100332n]

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