methyl 3-deoxy-3-(4-methylbenzamido)-1-thio-beta-D-galactopyranoside

ID: ALA260473

Chembl Id: CHEMBL260473

PubChem CID: 24776276

Max Phase: Preclinical

Molecular Formula: C15H21NO5S

Molecular Weight: 327.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H21NO5S/c1-8-3-5-9(6-4-8)14(20)16-11-12(18)10(7-17)21-15(22-2)13(11)19/h3-6,10-13,15,17-19H,7H2,1-2H3,(H,16,20)/t10-,11+,12+,13-,15+/m1/s1

Standard InChI Key:  MYAWDXDLUZEXBG-KDBYPZKRSA-N

Alternative Forms

1. Parent:

   

   ALA260473

   N-[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-(methylsulfanyl)oxan-4-yl]-4-methylbenzamide

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: 327.40

Molecular Weight (Monoisotopic): 327.1140

AlogP: -0.10

#Rotatable Bonds: 4

Polar Surface Area: 99.02

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.98

CX Basic pKa: ┄

CX LogP: 0.50

CX LogD: 0.50

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.62

Np Likeness Score: 0.19

References

1. Oberg CT, Leffler H, Nilsson UJ..  (2008)  Arginine binding motifs: design and synthesis of galactose-derived arginine tweezers as galectin-3 inhibitors.,  51  (7): [PMID:18318467] [10.1021/jm701266y]

2. Rajput VK, Leffler H, Nilsson UJ, Mukhopadhyay B..  (2014)  Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists.,  24  (15): [PMID:24973029] [10.1016/j.bmcl.2014.05.063]

Source

Source(1):

• Scientific Literature