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

ID: ALA2070526

Chembl Id: CHEMBL2070526

PubChem CID: 57523230

Max Phase: Preclinical

Molecular Formula: C23H37N2O11P

Molecular Weight: 548.53

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H37N2O11P/c1-7-33-22(29)18(13(2)3)25-37(30,35-16-10-8-15(31-5)9-11-16)36-21-19(24-14(4)27)23(32-6)34-17(12-26)20(21)28/h8-11,13,17-21,23,26,28H,7,12H2,1-6H3,(H,24,27)(H,25,30)/t17-,18+,19-,20-,21-,23+,37?/m1/s1

Standard InChI Key:  XNXHJIVSIMRYQF-HLQQUYBVSA-N

Alternative Forms

1. Parent:

   

   ALA2070526

   ethyl (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: 548.53

Molecular Weight (Monoisotopic): 548.2135

AlogP: 0.97

#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: 10.21

CX Basic pKa: ┄

CX LogP: 0.26

CX LogD: 0.26

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.20

Np Likeness Score: 0.64

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