Standard InChI: InChI=1S/C20H23ClO6/c1-26-14-5-2-11(3-6-14)8-13-9-12(4-7-15(13)21)20-19(25)18(24)17(23)16(10-22)27-20/h2-7,9,16-20,22-25H,8,10H2,1H3/t16-,17-,18+,19-,20+/m1/s1
Standard InChI Key: UEHTWMMZNLKDPS-OBKDMQGPSA-N
Associated Targets(Human)
Sodium/glucose cotransporter 2 2000 Activities
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Sodium/glucose cotransporter 1 1526 Activities
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Hepatocyte 2737 Activities
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Liver microsomes 16955 Activities
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Associated Targets(non-human)
Rattus norvegicus 775804 Activities
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Canis familiaris 36305 Activities
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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
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Properties
Molecular Weight: 394.85
Molecular Weight (Monoisotopic): 394.1183
AlogP: 1.45
#Rotatable Bonds: 5
Polar Surface Area: 99.38
Molecular Species: NEUTRAL
HBA: 6
HBD: 4
#RO5 Violations: 0
HBA (Lipinski): 6
HBD (Lipinski): 4
#RO5 Violations (Lipinski): 0
CX Acidic pKa: 12.57
CX Basic pKa:
CX LogP: 1.75
CX LogD: 1.75
Aromatic Rings: 2
Heavy Atoms: 27
QED Weighted: 0.61
Np Likeness Score: 0.85
References
1.Robinson RP, Mascitti V, Boustany-Kari CM, Carr CL, Foley PM, Kimoto E, Leininger MT, Lowe A, Klenotic MK, Macdonald JI, Maguire RJ, Masterson VM, Maurer TS, Miao Z, Patel JD, Préville C, Reese MR, She L, Steppan CM, Thuma BA, Zhu T.. (2010) C-Aryl glycoside inhibitors of SGLT2: Exploration of sugar modifications including C-5 spirocyclization., 20 (5):[PMID:20149653][10.1016/j.bmcl.2010.01.075]
2.Mascitti V, Maurer TS, Robinson RP, Bian J, Boustany-Kari CM, Brandt T, Collman BM, Kalgutkar AS, Klenotic MK, Leininger MT, Lowe A, Maguire RJ, Masterson VM, Miao Z, Mukaiyama E, Patel JD, Pettersen JC, Préville C, Samas B, She L, Sobol Z, Steppan CM, Stevens BD, Thuma BA, Tugnait M, Zeng D, Zhu T.. (2011) Discovery of a clinical candidate from the structurally unique dioxa-bicyclo[3.2.1]octane class of sodium-dependent glucose cotransporter 2 inhibitors., 54 (8):[PMID:21449606][10.1021/jm200049r]
3.Xu G, Lv B, Roberge JY, Xu B, Du J, Dong J, Chen Y, Peng K, Zhang L, Tang X, Feng Y, Xu M, Fu W, Zhang W, Zhu L, Deng Z, Sheng Z, Welihinda A, Sun X.. (2014) Design, synthesis, and biological evaluation of deuterated C-aryl glycoside as a potent and long-acting renal sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes., 57 (4):[PMID:24456245][10.1021/jm401780b]
