((2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl 2-(3-benzoylphenyl)propanoate

ID: ALA494865

Chembl Id: CHEMBL494865

PubChem CID: 44139591

Max Phase: Preclinical

Molecular Formula: C22H24O8

Molecular Weight: 416.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C(=O)OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O)c1cccc(C(=O)c2ccccc2)c1

Standard InChI:  InChI=1S/C22H24O8/c1-12(21(27)29-11-16-18(24)19(25)20(26)22(28)30-16)14-8-5-9-15(10-14)17(23)13-6-3-2-4-7-13/h2-10,12,16,18-20,22,24-26,28H,11H2,1H3/t12?,16-,18-,19+,20-,22-/m1/s1

Standard InChI Key:  BWNPGVAAYZIIHW-ORHVPNALSA-N

Alternative Forms

1. Parent:

   

   ALA494865

   ((2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl 2-(3-benzoylphenyl)propanoate

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: 416.43

Molecular Weight (Monoisotopic): 416.1471

AlogP: 0.36

#Rotatable Bonds: 6

Polar Surface Area: 133.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.30

CX Basic pKa: ┄

CX LogP: 1.35

CX LogD: 1.35

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.39

Np Likeness Score: 0.87

References

1. Gynther M, Ropponen J, Laine K, Leppänen J, Haapakoski P, Peura L, Järvinen T, Rautio J..  (2009)  Glucose promoiety enables glucose transporter mediated brain uptake of ketoprofen and indomethacin prodrugs in rats.,  52  (10): [PMID:19402664] [10.1021/jm8015409]

Source

Source(1):

• Scientific Literature