4-Chloro-3-(4-cyclopropylbenzyl)-1-(6-deoxy-6-{[ethoxy(oxo)acetyl]amino}-beta-D-glucopyranosyl)-1H-indole

ID: ALA3785234

Chembl Id: CHEMBL3785234

PubChem CID: 127034239

Max Phase: Preclinical

Molecular Formula: C28H31ClN2O7

Molecular Weight: 543.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(=O)NC[C@H]1O[C@@H](n2cc(Cc3ccc(C4CC4)cc3)c3c(Cl)cccc32)[C@H](O)[C@@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C28H31ClN2O7/c1-2-37-28(36)26(35)30-13-21-23(32)24(33)25(34)27(38-21)31-14-18(22-19(29)4-3-5-20(22)31)12-15-6-8-16(9-7-15)17-10-11-17/h3-9,14,17,21,23-25,27,32-34H,2,10-13H2,1H3,(H,30,35)/t21-,23-,24+,25-,27-/m1/s1

Standard InChI Key:  JOMFQRSAICZEOR-VRCQNKPTSA-N

Alternative Forms

1. Parent:

   

   ALA3785234

   ---

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: 543.02

Molecular Weight (Monoisotopic): 542.1820

AlogP: 2.42

#Rotatable Bonds: 7

Polar Surface Area: 130.25

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.64

CX Basic pKa: ┄

CX LogP: 3.77

CX LogD: 3.77

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.27

Np Likeness Score: 0.09

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