(2S)-ethyl 1-(((2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-4-yloxy)(4-methoxyphenoxy)phosphoryl)pyrrolidine-2-carboxylate

ID: ALA2070525

Chembl Id: CHEMBL2070525

PubChem CID: 70690954

Max Phase: Preclinical

Molecular Formula: C23H35N2O11P

Molecular Weight: 546.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@@H]1CCCN1P(=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/C23H35N2O11P/c1-5-33-22(29)17-7-6-12-25(17)37(30,35-16-10-8-15(31-3)9-11-16)36-21-19(24-14(2)27)23(32-4)34-18(13-26)20(21)28/h8-11,17-21,23,26,28H,5-7,12-13H2,1-4H3,(H,24,27)/t17-,18+,19+,20+,21+,23-,37?/m0/s1

Standard InChI Key:  BAQHSTDRXQABGA-INERGFOMSA-N

Alternative Forms

1. Parent:

   

   ALA2070525

   ethyl (2S)-1-[[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-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: 546.51

Molecular Weight (Monoisotopic): 546.1978

AlogP: 0.82

#Rotatable Bonds: 11

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: 12.09

CX Basic pKa: ┄

CX LogP: -0.35

CX LogD: -0.35

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.27

Np Likeness Score: 0.59

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