4-Chloro-3-(4-cyclopropylbenzyl)-1-[6-deoxy-6-(4-ethoxy-1H-1,2,3-triazol-1-yl)-beta-D-gluco-pyranosyl]-1H-indole

ID: ALA3787102

Chembl Id: CHEMBL3787102

Cas Number: 1443333-49-0

PubChem CID: 89634086

Max Phase: Preclinical

Molecular Formula: C28H31ClN4O5

Molecular Weight: 539.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cn(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/C28H31ClN4O5/c1-2-37-23-15-32(31-30-23)14-22-25(34)26(35)27(36)28(38-22)33-13-19(24-20(29)4-3-5-21(24)33)12-16-6-8-17(9-7-16)18-10-11-18/h3-9,13,15,18,22,25-28,34-36H,2,10-12,14H2,1H3/t22-,25-,26+,27-,28-/m1/s1

Standard InChI Key:  DJJUHVRVPQRWGI-FSKOWZIRSA-N

Alternative Forms

1. Parent:

   

   ALA3787102

   4-Chloro-3-[(4-cyclopropylphenyl)methyl]-1-[6-deoxy-6-(4-ethoxy-1H-1,2,3-triazol-1-yl)-beta-D-glucopyranosyl]-1H-indole

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: 539.03

Molecular Weight (Monoisotopic): 538.1983

AlogP: 3.43

#Rotatable Bonds: 8

Polar Surface Area: 114.79

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: 4.69

CX LogD: 4.69

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.31

Np Likeness Score: -0.16

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