arabinouridine-5'-[phenyl-(benzoxy-D-alaninyl)]-phosphate

ID: ALA1088774

PubChem CID: 46885777

Max Phase: Preclinical

Molecular Formula: C25H28N3O10P

Molecular Weight: 561.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](NP(=O)(OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@@H](O)[C@@H]1O)Oc1ccccc1)C(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C25H28N3O10P/c1-16(24(32)35-14-17-8-4-2-5-9-17)27-39(34,38-18-10-6-3-7-11-18)36-15-19-21(30)22(31)23(37-19)28-13-12-20(29)26-25(28)33/h2-13,16,19,21-23,30-31H,14-15H2,1H3,(H,27,34)(H,26,29,33)/t16-,19-,21-,22+,23-,39?/m1/s1

Standard InChI Key:  DKBXRLMSQKUCCW-BWFVNWMCSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1088774

   benzyl (2R)-2-[[[(2R,3S,4S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate

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: 561.48

Molecular Weight (Monoisotopic): 561.1512

AlogP: 1.08

#Rotatable Bonds: 11

Polar Surface Area: 178.41

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 9.59

CX Basic pKa: ┄

CX LogP: 1.06

CX LogD: 1.06

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: 0.46

References

1. Mehellou Y, Valente R, Mottram H, Walsby E, Mills KI, Balzarini J, McGuigan C..  (2010)  Phosphoramidates of 2'-beta-D-arabinouridine (AraU) as phosphate prodrugs; design, synthesis, in vitro activity and metabolism.,  18  (7): [PMID:20299228] [10.1016/j.bmc.2010.02.059]

Source

Source(1):

• Scientific Literature