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

ID: ALA2070524

Chembl Id: CHEMBL2070524

PubChem CID: 57523228

Max Phase: Preclinical

Molecular Formula: C28H39N2O11P

Molecular Weight: 610.60

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H39N2O11P/c1-17(2)23(27(34)38-16-19-9-7-6-8-10-19)30-42(35,40-21-13-11-20(36-4)12-14-21)41-26-24(29-18(3)32)28(37-5)39-22(15-31)25(26)33/h6-14,17,22-26,28,31,33H,15-16H2,1-5H3,(H,29,32)(H,30,35)/t22-,23+,24-,25-,26-,28+,42?/m1/s1

Standard InChI Key:  YWNNWOJXIPWAGI-UJJHOUTHSA-N

Alternative Forms

1. Parent:

   

   ALA2070524

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

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: 610.60

Molecular Weight (Monoisotopic): 610.2291

AlogP: 2.15

#Rotatable Bonds: 14

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: 10.21

CX Basic pKa: ┄

CX LogP: 1.63

CX LogD: 1.63

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.18

Np Likeness Score: 0.55

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