3-(4-Ethylphenylmethyl)-4-fluoro-1-(beta-D-glucopyranosyl)indole

ID: ALA3109020

Chembl Id: CHEMBL3109020

PubChem CID: 11654569

Max Phase: Preclinical

Molecular Formula: C23H26FNO5

Molecular Weight: 415.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(Cc2cn([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c3cccc(F)c23)cc1

Standard InChI:  InChI=1S/C23H26FNO5/c1-2-13-6-8-14(9-7-13)10-15-11-25(17-5-3-4-16(24)19(15)17)23-22(29)21(28)20(27)18(12-26)30-23/h3-9,11,18,20-23,26-29H,2,10,12H2,1H3/t18-,20-,21+,22-,23-/m1/s1

Standard InChI Key:  OJLFHAUEWOXGIM-DODNOZFWSA-N

Alternative Forms

1. Parent:

   

   ALA3109020

   (2R,3R,4S,5S,6R)-2-[3-[(4-ethylphenyl)methyl]-4-fluoroindol-1-yl]-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: 415.46

Molecular Weight (Monoisotopic): 415.1795

AlogP: 1.91

#Rotatable Bonds: 5

Polar Surface Area: 95.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.36

CX Basic pKa: ┄

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: 0.43

References

1. Nomura S, Yamamoto Y, Matsumura Y, Ohba K, Sakamaki S, Kimata H, Nakayama K, Kuriyama C, Matsushita Y, Ueta K, Tsuda-Tsukimoto M..  (2014)  Novel Indole-N-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes.,  5  (1): [PMID:24900773] [10.1021/ml400339b]

Source

Source(1):

• Scientific Literature