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

ID: ALA3785936

Chembl Id: CHEMBL3785936

PubChem CID: 89630320

Max Phase: Preclinical

Molecular Formula: C27H30BrClN2O5

Molecular Weight: 577.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCBr)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/C27H30BrClN2O5/c28-11-10-22(32)30-13-21-24(33)25(34)26(35)27(36-21)31-14-18(23-19(29)2-1-3-20(23)31)12-15-4-6-16(7-5-15)17-8-9-17/h1-7,14,17,21,24-27,33-35H,8-13H2,(H,30,32)/t21-,24-,25+,26-,27-/m1/s1

Standard InChI Key:  HQERINGMQUGLSK-BYBMWWPSSA-N

Alternative Forms

1. Parent:

   

   ALA3785936

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

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: 577.90

Molecular Weight (Monoisotopic): 576.1027

AlogP: 3.64

#Rotatable Bonds: 8

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: 12.37

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 4.03

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.31

Np Likeness Score: 0.10

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