4-Chloro-1-[6-(4-cyclopentyl-1H-1,2,3-triazol-1-yl)-6-deoxy-beta-D-glucopyranosyl]-3-(4-cyclopropylbenzyl)-1H-indole

ID: ALA3786186

Chembl Id: CHEMBL3786186

PubChem CID: 89630299

Max Phase: Preclinical

Molecular Formula: C31H35ClN4O4

Molecular Weight: 563.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O[C@@H]1[C@@H](O)[C@H](n2cc(Cc3ccc(C4CC4)cc3)c3c(Cl)cccc32)O[C@H](Cn2cc(C3CCCC3)nn2)[C@H]1O

Standard InChI:  InChI=1S/C31H35ClN4O4/c32-23-6-3-7-25-27(23)22(14-18-8-10-19(11-9-18)20-12-13-20)15-36(25)31-30(39)29(38)28(37)26(40-31)17-35-16-24(33-34-35)21-4-1-2-5-21/h3,6-11,15-16,20-21,26,28-31,37-39H,1-2,4-5,12-14,17H2/t26-,28-,29+,30-,31-/m1/s1

Standard InChI Key:  XRNKOEJLXXFMMZ-OVFXHNNVSA-N

Alternative Forms

1. Parent:

   

   ALA3786186

   (2R,3R,4S,5S,6R)-2-[4-chloro-3-[(4-cyclopropylphenyl)methyl]indol-1-yl]-6-[(4-cyclopentyltriazol-1-yl)methyl]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: 563.10

Molecular Weight (Monoisotopic): 562.2347

AlogP: 4.69

#Rotatable Bonds: 7

Polar Surface Area: 105.56

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.37

CX Basic pKa: 0.40

CX LogP: 5.70

CX LogD: 5.70

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.30

Np Likeness Score: -0.15

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