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

ID: ALA3785293

Chembl Id: CHEMBL3785293

PubChem CID: 89630302

Max Phase: Preclinical

Molecular Formula: C26H28Cl2N2O5

Molecular Weight: 519.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCl)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/C26H28Cl2N2O5/c27-11-21(31)29-12-20-23(32)24(33)25(34)26(35-20)30-13-17(22-18(28)2-1-3-19(22)30)10-14-4-6-15(7-5-14)16-8-9-16/h1-7,13,16,20,23-26,32-34H,8-12H2,(H,29,31)/t20-,23-,24+,25-,26-/m1/s1

Standard InChI Key:  BUJCKZHCUXHUJG-DDLBMNSQSA-N

Alternative Forms

1. Parent:

   

   ALA3785293

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

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: 519.43

Molecular Weight (Monoisotopic): 518.1375

AlogP: 3.10

#Rotatable Bonds: 7

Polar Surface Area: 103.95

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.36

CX Basic pKa: ┄

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.36

Np Likeness Score: 0.08

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