1-(6-Amino-6-deoxy-beta-D-glucopyranosyl)-4-chloro-3-(4-cyclopropylbenzyl)-1H-indole

ID: ALA3785403

Chembl Id: CHEMBL3785403

PubChem CID: 89630294

Max Phase: Preclinical

Molecular Formula: C24H27ClN2O4

Molecular Weight: 442.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  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/C24H27ClN2O4/c25-17-2-1-3-18-20(17)16(10-13-4-6-14(7-5-13)15-8-9-15)12-27(18)24-23(30)22(29)21(28)19(11-26)31-24/h1-7,12,15,19,21-24,28-30H,8-11,26H2/t19-,21-,22+,23-,24-/m1/s1

Standard InChI Key:  SWJOEFJDQJHSFK-PFKOEMKTSA-N

Alternative Forms

1. Parent:

   

   ALA3785403

   (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[4-chloro-3-[(4-cyclopropylphenyl)methyl]indol-1-yl]oxane-3,4,5-triol

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: 442.94

Molecular Weight (Monoisotopic): 442.1659

AlogP: 2.70

#Rotatable Bonds: 5

Polar Surface Area: 100.87

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.37

CX Basic pKa: 8.80

CX LogP: 3.25

CX LogD: 1.85

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: 0.45

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