4-Chloro-3-(5-(6-fluoro-3-pyridyl)-2-thienylmethyl)-1-(beta-D-glucopyranosyl)benzene

ID: ALA2414617

Chembl Id: CHEMBL2414617

PubChem CID: 25224975

Max Phase: Preclinical

Molecular Formula: C22H21ClFNO5S

Molecular Weight: 465.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(-c4ccc(F)nc4)s3)c2)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C22H21ClFNO5S/c23-15-4-1-11(22-21(29)20(28)19(27)16(10-26)30-22)7-13(15)8-14-3-5-17(31-14)12-2-6-18(24)25-9-12/h1-7,9,16,19-22,26-29H,8,10H2/t16-,19-,20+,21-,22+/m1/s1

Standard InChI Key:  WQWNUPFPUXHKAQ-OSKXVONFSA-N

Alternative Forms

1. Parent:

   

   ALA2414617

   (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[5-(6-fluoropyridin-3-yl)thiophen-2-yl]methyl]phenyl]-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: 465.93

Molecular Weight (Monoisotopic): 465.0813

AlogP: 2.71

#Rotatable Bonds: 5

Polar Surface Area: 103.04

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.57

CX Basic pKa: ┄

CX LogP: 2.79

CX LogD: 2.79

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.43

Np Likeness Score: 0.13

References

1. Koga Y, Sakamaki S, Hongu M, Kawanishi E, Sakamoto T, Yamamoto Y, Kimata H, Nakayama K, Kuriyama C, Matsushita Y, Ueta K, Tsuda-Tsukimoto M, Nomura S..  (2013)  C-Glucosides with heteroaryl thiophene as novel sodium-dependent glucose cotransporter 2 inhibitors.,  21  (17): [PMID:23809172] [10.1016/j.bmc.2013.05.048]

2. 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