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

ID: ALA2070514

Chembl Id: CHEMBL2070514

PubChem CID: 57523696

Max Phase: Preclinical

Molecular Formula: C24H37N2O11P

Molecular Weight: 560.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)OC(=O)[C@@H]1CCCN1P(=O)(Oc1ccc(OC)cc1)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]1NC(C)=O

Standard InChI:  InChI=1S/C24H37N2O11P/c1-5-14(2)34-23(30)18-7-6-12-26(18)38(32,36-17-10-8-16(33-4)9-11-17)37-22-20(25-15(3)28)24(31)35-19(13-27)21(22)29/h8-11,14,18-22,24,27,29,31H,5-7,12-13H2,1-4H3,(H,25,28)/t14?,18-,19+,20+,21+,22+,24-,38?/m0/s1

Standard InChI Key:  NNQBXPPIAIRCKG-XBSJAETRSA-N

Alternative Forms

1. Parent:

   

   ALA2070514

   butan-2-yl (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: 560.54

Molecular Weight (Monoisotopic): 560.2135

AlogP: 0.95

#Rotatable Bonds: 11

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: -0.06

CX LogD: -0.06

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: 0.69

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