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

ID: ALA3785614

Chembl Id: CHEMBL3785614

PubChem CID: 89630298

Max Phase: Preclinical

Molecular Formula: C29H31ClN4O4

Molecular Weight: 535.04

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@@H]1[C@@H](O)[C@H](n2cc(Cc3ccc(C4CC4)cc3)c3c(Cl)cccc32)O[C@H](Cn2cc(C3CC3)nn2)[C@H]1O

Standard InChI:  InChI=1S/C29H31ClN4O4/c30-21-2-1-3-23-25(21)20(12-16-4-6-17(7-5-16)18-8-9-18)13-34(23)29-28(37)27(36)26(35)24(38-29)15-33-14-22(31-32-33)19-10-11-19/h1-7,13-14,18-19,24,26-29,35-37H,8-12,15H2/t24-,26-,27+,28-,29-/m1/s1

Standard InChI Key:  CPEJJGJBLHVSNS-KRZJEZTLSA-N

Alternative Forms

1. Parent:

   

   ALA3785614

   (2R,3R,4S,5S,6R)-2-[4-chloro-3-[(4-cyclopropylphenyl)methyl]indol-1-yl]-6-[(4-cyclopropyltriazol-1-yl)methyl]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: 535.04

Molecular Weight (Monoisotopic): 534.2034

AlogP: 3.91

#Rotatable Bonds: 7

Polar Surface Area: 105.56

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.37

CX Basic pKa: 0.40

CX LogP: 4.81

CX LogD: 4.81

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.33

Np Likeness Score: -0.15

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