1-(beta-D-Glucopyranosyl)-4-methyl-3-(5-(4-fluorophenyl)-2-thienylmethyl)benzene

ID: ALA1243275

Chembl Id: CHEMBL1243275

PubChem CID: 52944051

Max Phase: Preclinical

Molecular Formula: C24H25FO6S

Molecular Weight: 460.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(-c2ccc(F)cc2)s1

Standard InChI:  InChI=1S/C24H25FO6S/c1-13-3-2-4-18(30-24-23(29)22(28)21(27)19(12-26)31-24)17(13)11-16-9-10-20(32-16)14-5-7-15(25)8-6-14/h2-10,19,21-24,26-29H,11-12H2,1H3/t19-,21-,22+,23-,24-/m1/s1

Standard InChI Key:  LQCIKRNQMUFICQ-PFKOEMKTSA-N

Alternative Forms

1. Parent:

   

   ALA1243275

   (2S,3R,4S,5S,6R)-2-[2-[[5-(4-fluorophenyl)thiophen-2-yl]methyl]-3-methylphenoxy]-6-(hydroxymethyl)oxane-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: 460.52

Molecular Weight (Monoisotopic): 460.1356

AlogP: 2.63

#Rotatable Bonds: 6

Polar Surface Area: 99.38

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.45

Np Likeness Score: 0.45

References

1. 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]

Source

Source(1):

• Scientific Literature