1-O-Methyl-2-acetamido-2-deoxy-3-O-[p-methoxyphenyl(ethoxy-(L)-sarcosinyl)phosphate-alpha(D)-glucopyranose

ID: ALA2070527

Chembl Id: CHEMBL2070527

PubChem CID: 57523231

Max Phase: Preclinical

Molecular Formula: C21H33N2O11P

Molecular Weight: 520.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN(C)P(=O)(Oc1ccc(OC)cc1)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](OC)[C@@H]1NC(C)=O

Standard InChI:  InChI=1S/C21H33N2O11P/c1-6-31-17(26)11-23(3)35(28,33-15-9-7-14(29-4)8-10-15)34-20-18(22-13(2)25)21(30-5)32-16(12-24)19(20)27/h7-10,16,18-21,24,27H,6,11-12H2,1-5H3,(H,22,25)/t16-,18-,19-,20-,21+,35?/m1/s1

Standard InChI Key:  QSJXTDWVSYVXNB-AHJJYQISSA-N

Alternative Forms

1. Parent:

   

   ALA2070527

   ethyl 2-[[[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-(4-methoxyphenoxy)phosphoryl]-methylamino]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: 520.47

Molecular Weight (Monoisotopic): 520.1822

AlogP: 0.29

#Rotatable Bonds: 12

Polar Surface Area: 162.32

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.06

CX Basic pKa: ┄

CX LogP: -0.97

CX LogD: -0.97

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.26

Np Likeness Score: 0.62

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