4-Chloro-3-(4-cyclopropylbenzyl)-1-{6-deoxy-6-[4-(methoxycarbonyl)-1H-1,2,3-triazol-1-yl]-beta-D-glucopyranosyl}-1H-indole

ID: ALA3786435

Chembl Id: CHEMBL3786435

PubChem CID: 89634111

Max Phase: Preclinical

Molecular Formula: C28H29ClN4O6

Molecular Weight: 553.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1cn(C[C@H]2O[C@@H](n3cc(Cc4ccc(C5CC5)cc4)c4c(Cl)cccc43)[C@H](O)[C@@H](O)[C@@H]2O)nn1

Standard InChI:  InChI=1S/C28H29ClN4O6/c1-38-28(37)20-13-32(31-30-20)14-22-24(34)25(35)26(36)27(39-22)33-12-18(23-19(29)3-2-4-21(23)33)11-15-5-7-16(8-6-15)17-9-10-17/h2-8,12-13,17,22,24-27,34-36H,9-11,14H2,1H3/t22-,24-,25+,26-,27-/m1/s1

Standard InChI Key:  FHNZEYFYMXTVHV-UIKHAHSZSA-N

Alternative Forms

1. Parent:

   

   ALA3786435

   methyl 1-[[(2R,3S,4S,5R,6R)-6-[4-chloro-3-[(4-cyclopropylphenyl)methyl]indol-1-yl]-3,4,5-trihydroxyoxan-2-yl]methyl]triazole-4-carboxylate

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: 553.02

Molecular Weight (Monoisotopic): 552.1776

AlogP: 2.82

#Rotatable Bonds: 7

Polar Surface Area: 131.86

Molecular Species: NEUTRAL

HBA: 10

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.30

Np Likeness Score: -0.23

References

1. Chu KF, Yao CH, Song JS, Chen CT, Yeh TK, Hsieh TC, Huang CY, Wang MH, Wu SH, Chang WE, Chao YS, Lee JC..  (2016)  N-Indolylglycosides bearing modifications at the glucose C6-position as sodium-dependent glucose co-transporter 2 inhibitors.,  24  (10): [PMID:27075813] [10.1016/j.bmc.2016.03.058]

Source

Source(1):

• Scientific Literature