4-Chloro-3-(4-cyclopropylbenzyl)-1-{6-deoxy-6-[(1,2-oxazol-5-ylcarbonyl)amino]-beta-D-glucopyranosyl}-1H-indole

ID: ALA3785202

Chembl Id: CHEMBL3785202

PubChem CID: 89630307

Max Phase: Preclinical

Molecular Formula: C28H28ClN3O6

Molecular Weight: 538.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC[C@H]1O[C@@H](n2cc(Cc3ccc(C4CC4)cc3)c3c(Cl)cccc32)[C@H](O)[C@@H](O)[C@@H]1O)c1ccno1

Standard InChI:  InChI=1S/C28H28ClN3O6/c29-19-2-1-3-20-23(19)18(12-15-4-6-16(7-5-15)17-8-9-17)14-32(20)28-26(35)25(34)24(33)22(37-28)13-30-27(36)21-10-11-31-38-21/h1-7,10-11,14,17,22,24-26,28,33-35H,8-9,12-13H2,(H,30,36)/t22-,24-,25+,26-,28-/m1/s1

Standard InChI Key:  DMKBPKHKOBBPHY-HOZVGSINSA-N

Alternative Forms

1. Parent:

   

   ALA3785202

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

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: 538.00

Molecular Weight (Monoisotopic): 537.1667

AlogP: 3.16

#Rotatable Bonds: 7

Polar Surface Area: 129.98

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.36

CX Basic pKa: ┄

CX LogP: 3.21

CX LogD: 3.21

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.28

Np Likeness Score: -0.27

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