[2'-(3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-biphenyl-3-yl]-acetic acid methyl ester

ID: ALA2303932

Chembl Id: CHEMBL2303932

PubChem CID: 71719065

Max Phase: Preclinical

Molecular Formula: C21H24O8

Molecular Weight: 404.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)Cc1cccc(-c2ccccc2O[C@H]2O[C@H](CO)[C@@H](O)[C@@H](O)[C@@H]2O)c1

Standard InChI:  InChI=1S/C21H24O8/c1-27-17(23)10-12-5-4-6-13(9-12)14-7-2-3-8-15(14)28-21-20(26)19(25)18(24)16(11-22)29-21/h2-9,16,18-22,24-26H,10-11H2,1H3/t16-,18-,19-,20+,21+/m1/s1

Standard InChI Key:  ZAKZBPCBIXJUCE-JFHUYLGKSA-N

Alternative Forms

1. Parent:

   

   ALA2303932

   methyl 2-[3-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]acetate

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: 404.42

Molecular Weight (Monoisotopic): 404.1471

AlogP: 0.25

#Rotatable Bonds: 6

Polar Surface Area: 125.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: ┄

CX LogP: 0.83

CX LogD: 0.83

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: 1.10

References

1. Kogan TP, Dupré B, Keller KM, Scott IL, Bui H, Market RV, Beck PJ, Voytus JA, Revelle BM, Scott D..  (1995)  Rational design and synthesis of small molecule, non-oligosaccharide selectin inhibitors: (alpha-D-mannopyranosyloxy)biphenyl-substituted carboxylic acids.,  38  (26): [PMID:8544173] [10.1021/jm00026a004]

Source

Source(1):

• Scientific Literature