(R)-2-((2S,3R,4S,5S,6R)-2-((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)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy)-3-phenylpropanoic acid

ID: ALA2204273

Chembl Id: CHEMBL2204273

PubChem CID: 71450419

Max Phase: Preclinical

Molecular Formula: C27H38O17

Molecular Weight: 634.58

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](O)[C@H](O[C@H](Cc2ccccc2)C(=O)O)[C@H]1O)C(=O)OC

Standard InChI:  InChI=1S/C27H38O17/c1-11-15(29)17(31)18(32)26(40-11)43-21(24(36)38-2)22(25(37)39-3)44-27-19(33)20(16(30)14(10-28)42-27)41-13(23(34)35)9-12-7-5-4-6-8-12/h4-8,11,13-22,26-33H,9-10H2,1-3H3,(H,34,35)/t11-,13+,14+,15+,16-,17+,18-,19+,20-,21+,22+,26-,27-/m0/s1

Standard InChI Key:  OBGSYIUACCHCHT-RVTKUGSFSA-N

Alternative Forms

1. Parent:

   

   ALA2204273

   (2R)-2-[(2S,3R,4S,5S,6R)-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-3,5-dihydroxy-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: 634.58

Molecular Weight (Monoisotopic): 634.2109

AlogP: -3.55

#Rotatable Bonds: 13

Polar Surface Area: 257.43

Molecular Species: ACID

HBA: 16

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 17

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.43

CX Basic pKa: ┄

CX LogP: -1.69

CX LogD: -5.08

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.10

Np Likeness Score: 1.28

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