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

ID: ALA3786014

Chembl Id: CHEMBL3786014

PubChem CID: 89630301

Max Phase: Preclinical

Molecular Formula: C28H31ClN2O5

Molecular Weight: 511.02

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)C1CC1

Standard InChI:  InChI=1S/C28H31ClN2O5/c29-20-2-1-3-21-23(20)19(12-15-4-6-16(7-5-15)17-8-9-17)14-31(21)28-26(34)25(33)24(32)22(36-28)13-30-27(35)18-10-11-18/h1-7,14,17-18,22,24-26,28,32-34H,8-13H2,(H,30,35)/t22-,24-,25+,26-,28-/m1/s1

Standard InChI Key:  FOAMFDVMYDTVIE-HOZVGSINSA-N

Alternative Forms

1. Parent:

   

   ALA3786014

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

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: 511.02

Molecular Weight (Monoisotopic): 510.1921

AlogP: 3.27

#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: 12.37

CX Basic pKa: ┄

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.39

Np Likeness Score: -0.07

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