1-O-Methyl-2-acetamido-2-deoxy-3-O-[4-methoxyphenyl(benzyloxy-(L)-alaninyl)]-phosphate-alpha(D)-glucopyranose

ID: ALA2070523

Chembl Id: CHEMBL2070523

PubChem CID: 57523227

Max Phase: Preclinical

Molecular Formula: C26H35N2O11P

Molecular Weight: 582.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OP(=O)(N[C@@H](C)C(=O)OCc2ccccc2)O[C@H]2[C@H](O)[C@@H](CO)O[C@H](OC)[C@@H]2NC(C)=O)cc1

Standard InChI:  InChI=1S/C26H35N2O11P/c1-16(25(32)36-15-18-8-6-5-7-9-18)28-40(33,38-20-12-10-19(34-3)11-13-20)39-24-22(27-17(2)30)26(35-4)37-21(14-29)23(24)31/h5-13,16,21-24,26,29,31H,14-15H2,1-4H3,(H,27,30)(H,28,33)/t16-,21+,22+,23+,24+,26-,40?/m0/s1

Standard InChI Key:  LOMLYAZTBWZFRF-HUSOZMOHSA-N

Alternative Forms

1. Parent:

   

   ALA2070523

   benzyl (2S)-2-[[[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-(4-methoxyphenoxy)phosphoryl]amino]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: 582.54

Molecular Weight (Monoisotopic): 582.1978

AlogP: 1.52

#Rotatable Bonds: 13

Polar Surface Area: 171.11

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.22

CX Basic pKa: ┄

CX LogP: 0.74

CX LogD: 0.74

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.20

Np Likeness Score: 0.58

References

1. Serpi M, Bibbo R, Rat S, Roberts H, Hughes C, Caterson B, Alcaraz MJ, Gibert AT, Verson CR, McGuigan C..  (2012)  Novel phosphoramidate prodrugs of N-acetyl-(D)-glucosamine with antidegenerative activity on bovine and human cartilage explants.,  55  (10): [PMID:22501024] [10.1021/jm300074y]

Source

Source(1):

• Scientific Literature