4-Chloro-3-(4-cyclopropylbenzyl)-1-{6-deoxy-6-[(thiophen-2-ylacetyl)amino]-beta-D-glucopyranosyl}-1H-indole

ID: ALA3786041

Chembl Id: CHEMBL3786041

PubChem CID: 89630303

Max Phase: Preclinical

Molecular Formula: C30H31ClN2O5S

Molecular Weight: 567.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1cccs1)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/C30H31ClN2O5S/c31-22-4-1-5-23-26(22)20(13-17-6-8-18(9-7-17)19-10-11-19)16-33(23)30-29(37)28(36)27(35)24(38-30)15-32-25(34)14-21-3-2-12-39-21/h1-9,12,16,19,24,27-30,35-37H,10-11,13-15H2,(H,32,34)/t24-,27-,28+,29-,30-/m1/s1

Standard InChI Key:  PUVHWUMZTLKKTH-YMIJDRNOSA-N

Alternative Forms

1. Parent:

   

   ALA3786041

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

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: 567.11

Molecular Weight (Monoisotopic): 566.1642

AlogP: 4.16

#Rotatable Bonds: 8

Polar Surface Area: 103.95

Molecular Species: NEUTRAL

HBA: 7

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: 4.82

CX LogD: 4.82

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.26

Np Likeness Score: -0.41

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