2',2'-Difluoro-2'-deoxycytidine-5'-O-[N-(benzoyl)]phosphoramidate

ID: ALA3236421

Chembl Id: CHEMBL3236421

PubChem CID: 90654416

Max Phase: Preclinical

Molecular Formula: C16H17F2N4O7P

Molecular Weight: 446.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccn([C@@H]2O[C@H](COP(=O)(O)NC(=O)c3ccccc3)[C@@H](O)C2(F)F)c(=O)n1

Standard InChI:  InChI=1S/C16H17F2N4O7P/c17-16(18)12(23)10(29-14(16)22-7-6-11(19)20-15(22)25)8-28-30(26,27)21-13(24)9-4-2-1-3-5-9/h1-7,10,12,14,23H,8H2,(H2,19,20,25)(H2,21,24,26,27)/t10-,12-,14-/m1/s1

Standard InChI Key:  FLTYXOKRJBGVOB-MPKXVKKWSA-N

Alternative Forms

1. Parent:

   

   ALA3236421

   [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy-N-benzoylphosphonamidic acid

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: 446.30

Molecular Weight (Monoisotopic): 446.0803

AlogP: 0.27

#Rotatable Bonds: 6

Polar Surface Area: 166.00

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.51

CX Basic pKa: ┄

CX LogP: -0.32

CX LogD: -2.70

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: 0.59

References

1. Baraniak J, Pietkiewicz A, Kaczmarek R, Radzikowska E, Kulik K, Krolewska K, Cieslak M, Krakowiak A, Nawrot B..  (2014)  N-Acyl-phosphoramidates as potential novel form of gemcitabine prodrugs.,  22  (7): [PMID:24631359] [10.1016/j.bmc.2014.02.034]

Source

Source(1):

• Scientific Literature