(R)-2-((2R,3S,4R,5R,6S)-3-(benzoyloxy)-6-((2R,3R)-1,4-dimethoxy-1,4-dioxo-3-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)butan-2-yloxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoic acid

ID: ALA2204272

Chembl Id: CHEMBL2204272

PubChem CID: 71452242

Max Phase: Preclinical

Molecular Formula: C34H42O18

Molecular Weight: 738.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)[C@@H](O[C@@H]1O[C@H](CO)[C@H](OC(=O)c2ccccc2)[C@H](O[C@H](Cc2ccccc2)C(=O)O)[C@H]1O)C(=O)OC

Standard InChI:  InChI=1S/C34H42O18/c1-16-21(36)22(37)23(38)33(47-16)51-27(31(43)45-2)28(32(44)46-3)52-34-24(39)26(48-19(29(40)41)14-17-10-6-4-7-11-17)25(20(15-35)49-34)50-30(42)18-12-8-5-9-13-18/h4-13,16,19-28,33-39H,14-15H2,1-3H3,(H,40,41)/t16-,19+,20+,21+,22+,23-,24+,25-,26+,27+,28+,33-,34-/m0/s1

Standard InChI Key:  PNXXPGMPUWBOLW-FUFHFADFSA-N

Alternative Forms

1. Parent:

   

   ALA2204272

   (2R)-2-[(2S,3R,4R,5S,6R)-5-benzoyloxy-2-[(2R,3R)-1,4-dimethoxy-1,4-dioxo-3-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxybutan-2-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-phenylpropanoic acid

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: 738.69

Molecular Weight (Monoisotopic): 738.2371

AlogP: -1.68

#Rotatable Bonds: 15

Polar Surface Area: 263.50

Molecular Species: ACID

HBA: 17

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.29

CX Basic pKa: ┄

CX LogP: 0.81

CX LogD: -2.62

Aromatic Rings: 2

Heavy Atoms: 52

QED Weighted: 0.09

Np Likeness Score: 1.18

References

1. Calosso M, Charpentier D, Vaillancourt M, Bencheqroun M, St-Pierre G, Wilkes BC, Guindon Y..  (2012)  A new approach to explore the binding space of polysaccharide-based ligands: selectin antagonists.,  3  (12): [PMID:24900426] [10.1021/ml300263x]

2. Calosso M, Tambutet G, Charpentier D, St-Pierre G, Vaillancourt M, Bencheqroun M, Gratton JP, Prévost M, Guindon Y..  (2014)  Acyclic tethers mimicking subunits of polysaccharide ligands: selectin antagonists.,  5  (9): [PMID:25221666] [10.1021/ml500266x]

Source

Source(1):

• Scientific Literature