2-Acetamido-2-deoxy-3-O-[4-methoxyphenyl-(cyclohexyloxy-(L)-prolinyl)]-phosphate-alpha(D)-glucopyranose

ID: ALA2070515

Chembl Id: CHEMBL2070515

PubChem CID: 57523189

Max Phase: Preclinical

Molecular Formula: C26H39N2O11P

Molecular Weight: 586.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OP(=O)(O[C@H]2[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]2NC(C)=O)N2CCC[C@H]2C(=O)OC2CCCCC2)cc1

Standard InChI:  InChI=1S/C26H39N2O11P/c1-16(30)27-22-24(23(31)21(15-29)37-26(22)33)39-40(34,38-19-12-10-17(35-2)11-13-19)28-14-6-9-20(28)25(32)36-18-7-4-3-5-8-18/h10-13,18,20-24,26,29,31,33H,3-9,14-15H2,1-2H3,(H,27,30)/t20-,21+,22+,23+,24+,26-,40?/m0/s1

Standard InChI Key:  RYKIMJFQYOOLED-JBVMDQCASA-N

Alternative Forms

1. Parent:

   

   ALA2070515

   cyclohexyl (2S)-1-[[(2S,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-(4-methoxyphenoxy)phosphoryl]pyrrolidine-2-carboxylate

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: 586.58

Molecular Weight (Monoisotopic): 586.2291

AlogP: 1.48

#Rotatable Bonds: 10

Polar Surface Area: 173.32

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.55

CX Basic pKa: ┄

CX LogP: 0.45

CX LogD: 0.45

Aromatic Rings: 1

Heavy Atoms: 40

QED Weighted: 0.23

Np Likeness Score: 0.68

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