4-Chloro-3-(4-cyclopropylbenzyl)-1-{6-deoxy-6-[(4-methoxybenzoyl)amino]-beta-D-gluco-pyranosyl}-1H-indole

ID: ALA3785439

Chembl Id: CHEMBL3785439

PubChem CID: 89634090

Max Phase: Preclinical

Molecular Formula: C32H33ClN2O6

Molecular Weight: 577.08

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)NC[C@H]2O[C@@H](n3cc(Cc4ccc(C5CC5)cc4)c4c(Cl)cccc43)[C@H](O)[C@@H](O)[C@@H]2O)cc1

Standard InChI:  InChI=1S/C32H33ClN2O6/c1-40-23-13-11-21(12-14-23)31(39)34-16-26-28(36)29(37)30(38)32(41-26)35-17-22(27-24(33)3-2-4-25(27)35)15-18-5-7-19(8-6-18)20-9-10-20/h2-8,11-14,17,20,26,28-30,32,36-38H,9-10,15-16H2,1H3,(H,34,39)/t26-,28-,29+,30-,32-/m1/s1

Standard InChI Key:  ZBRZAXAJGAKPNP-RRFVWWEKSA-N

Alternative Forms

1. Parent:

   

   ALA3785439

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

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: 577.08

Molecular Weight (Monoisotopic): 576.2027

AlogP: 4.18

#Rotatable Bonds: 8

Polar Surface Area: 113.18

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.25

Np Likeness Score: 0.00

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