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

ID: ALA3787647

Chembl Id: CHEMBL3787647

PubChem CID: 89634117

Max Phase: Preclinical

Molecular Formula: C27H27ClN4O6

Molecular Weight: 538.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cn(C[C@H]2O[C@@H](n3cc(Cc4ccc(C5CC5)cc4)c4c(Cl)cccc43)[C@H](O)[C@@H](O)[C@@H]2O)nn1

Standard InChI:  InChI=1S/C27H27ClN4O6/c28-18-2-1-3-20-22(18)17(10-14-4-6-15(7-5-14)16-8-9-16)11-32(20)26-25(35)24(34)23(33)21(38-26)13-31-12-19(27(36)37)29-30-31/h1-7,11-12,16,21,23-26,33-35H,8-10,13H2,(H,36,37)/t21-,23-,24+,25-,26-/m1/s1

Standard InChI Key:  DIBSKUATJLGIRS-XDXGNBCUSA-N

Alternative Forms

1. Parent:

   

   ALA3787647

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

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: 538.99

Molecular Weight (Monoisotopic): 538.1619

AlogP: 2.73

#Rotatable Bonds: 7

Polar Surface Area: 142.86

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.02

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 0.47

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.28

Np Likeness Score: -0.17

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