4-Chloro-1-(6-{[4-(chloromethyl)benzoyl]amino}-6-deoxy-beta-D-glucopyranosyl)-3-(4-cyclopropylbenzyl)-1H-indole

ID: ALA3785193

Chembl Id: CHEMBL3785193

PubChem CID: 127034247

Max Phase: Preclinical

Molecular Formula: C32H32Cl2N2O5

Molecular Weight: 595.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC[C@H]1O[C@@H](n2cc(Cc3ccc(C4CC4)cc3)c3c(Cl)cccc32)[C@H](O)[C@@H](O)[C@@H]1O)c1ccc(CCl)cc1

Standard InChI:  InChI=1S/C32H32Cl2N2O5/c33-15-19-6-10-22(11-7-19)31(40)35-16-26-28(37)29(38)30(39)32(41-26)36-17-23(27-24(34)2-1-3-25(27)36)14-18-4-8-20(9-5-18)21-12-13-21/h1-11,17,21,26,28-30,32,37-39H,12-16H2,(H,35,40)/t26-,28-,29+,30-,32-/m1/s1

Standard InChI Key:  GWYOLSGNVWWNCS-RRFVWWEKSA-N

Alternative Forms

1. Parent:

   

   ALA3785193

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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: 595.52

Molecular Weight (Monoisotopic): 594.1688

AlogP: 4.91

#Rotatable Bonds: 8

Polar Surface Area: 103.95

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.37

CX Basic pKa: ┄

CX LogP: 5.51

CX LogD: 5.51

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.22

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