1-[6-(Acetylamino)-6-deoxy-beta-D-glucopyranosyl]-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole

ID: ALA3787515

Chembl Id: CHEMBL3787515

Cas Number: 1443333-67-2

PubChem CID: 71604270

Max Phase: Preclinical

Molecular Formula: C26H29ClN2O5

Molecular Weight: 484.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)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/C26H29ClN2O5/c1-14(30)28-12-21-23(31)24(32)25(33)26(34-21)29-13-18(22-19(27)3-2-4-20(22)29)11-15-5-7-16(8-6-15)17-9-10-17/h2-8,13,17,21,23-26,31-33H,9-12H2,1H3,(H,28,30)/t21-,23-,24+,25-,26-/m1/s1

Standard InChI Key:  BILGTWHYSCNCRU-XDXGNBCUSA-N

Alternative Forms

1. Parent:

   

   ALA3787515

   1-[6-(Acetylamino)-6-deoxy-beta-D-glucopyranosyl]-4-chloro-3-[(4-cyclopropylphenyl)methyl]-1H-indole

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: 484.98

Molecular Weight (Monoisotopic): 484.1765

AlogP: 2.88

#Rotatable Bonds: 6

Polar Surface Area: 103.95

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: 0.20

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