(2R,3S,4S,5S,6R)-3-acetoxy-5-hydroxy-6-(hydroxymethyl)-2-methoxy-tetrahydro-2H-pyran-4-yl 4-methylbenzoate

ID: ALA471376

Chembl Id: CHEMBL471376

PubChem CID: 44561021

Max Phase: Preclinical

Molecular Formula: C17H22O8

Molecular Weight: 354.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](OC(=O)c2ccc(C)cc2)[C@@H]1OC(C)=O

Standard InChI:  InChI=1S/C17H22O8/c1-9-4-6-11(7-5-9)16(21)25-14-13(20)12(8-18)24-17(22-3)15(14)23-10(2)19/h4-7,12-15,17-18,20H,8H2,1-3H3/t12-,13+,14+,15+,17-/m1/s1

Standard InChI Key:  IYJMKTZAMJWCQH-JLHDYFKBSA-N

Alternative Forms

1. Parent:

   

   ALA471376

   Methyl 2-O-Acetyl-3-O-(4-Methylbenzoyl)-Beta-D-Talopyranoside

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: 354.36

Molecular Weight (Monoisotopic): 354.1315

AlogP: 0.18

#Rotatable Bonds: 5

Polar Surface Area: 111.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.01

CX Basic pKa: ┄

CX LogP: 1.16

CX LogD: 1.16

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: 1.67

References

1. Oberg CT, Blanchard H, Leffler H, Nilsson UJ..  (2008)  Protein subtype-targeting through ligand epimerization: talose-selectivity of galectin-4 and galectin-8.,  18  (13): [PMID:18539029] [10.1016/j.bmcl.2008.05.066]

2. Bum-Erdene K, Collins PM, Hugo MW, Tarighat SS, Fei F, Kishor C, Leffler H, Nilsson UJ, Groffen J, Grice ID, Heisterkamp N, Blanchard H..  (2022)  Novel Selective Galectin-3 Antagonists Are Cytotoxic to Acute Lymphoblastic Leukemia.,  65  (8.0): [PMID:35427125] [10.1021/acs.jmedchem.1c01296]

Source

Source(1):

• Scientific Literature