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

ID: ALA3786347

Chembl Id: CHEMBL3786347

PubChem CID: 127034238

Max Phase: Preclinical

Molecular Formula: C27H29ClN2O7

Molecular Weight: 528.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C(=O)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/C27H29ClN2O7/c1-36-27(35)25(34)29-12-20-22(31)23(32)24(33)26(37-20)30-13-17(21-18(28)3-2-4-19(21)30)11-14-5-7-15(8-6-14)16-9-10-16/h2-8,13,16,20,22-24,26,31-33H,9-12H2,1H3,(H,29,34)/t20-,22-,23+,24-,26-/m1/s1

Standard InChI Key:  UZDYFYYKVXSYFM-DNMDETFRSA-N

Alternative Forms

1. Parent:

   

   ALA3786347

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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: 528.99

Molecular Weight (Monoisotopic): 528.1663

AlogP: 2.03

#Rotatable Bonds: 6

Polar Surface Area: 130.25

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.60

CX Basic pKa: ┄

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.28

Np Likeness Score: 0.23

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