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

ID: ALA1923802

Chembl Id: CHEMBL1923802

PubChem CID: 54768083

Max Phase: Preclinical

Molecular Formula: C20H24O8

Molecular Weight: 392.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2cc([C@H](C)C(=O)OC[C@H]3O[C@H](O)[C@H](O)[C@@H](O)[C@@H]3O)ccc2c1

Standard InChI:  InChI=1S/C20H24O8/c1-10(11-3-4-13-8-14(26-2)6-5-12(13)7-11)19(24)27-9-15-16(21)17(22)18(23)20(25)28-15/h3-8,10,15-18,20-23,25H,9H2,1-2H3/t10-,15+,16+,17-,18+,20-/m0/s1

Standard InChI Key:  QIDXRLSRXDOWQH-UPVJBQKYSA-N

Alternative Forms

1. Parent:

   

   ALA1923802

   [(2R,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl (2S)-2-(6-methoxynaphthalen-2-yl)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: 392.40

Molecular Weight (Monoisotopic): 392.1471

AlogP: 0.29

#Rotatable Bonds: 5

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: 11.30

CX Basic pKa: ┄

CX LogP: 0.72

CX LogD: 0.72

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: 1.01

References

1. Fan W, Wu Y, Li XK, Yao N, Li X, Yu YG, Hai L..  (2011)  Design, synthesis and biological evaluation of brain-specific glucosyl thiamine disulfide prodrugs of naproxen.,  46  (9): [PMID:21641697] [10.1016/j.ejmech.2011.05.029]

Source

Source(1):

• Scientific Literature