2',2'-Difluoro-2'-deoxycytidine-5'-O-[N-(3-carbonyl-pyridine)]thiophosphoramidate

ID: ALA3236418

Chembl Id: CHEMBL3236418

PubChem CID: 86302310

Max Phase: Preclinical

Molecular Formula: C15H16F2N5O6PS

Molecular Weight: 463.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccn([C@@H]2O[C@H](COP(=O)(S)NC(=O)c3cccnc3)[C@@H](O)C2(F)F)c(=O)n1

Standard InChI:  InChI=1S/C15H16F2N5O6PS/c16-15(17)11(23)9(28-13(15)22-5-3-10(18)20-14(22)25)7-27-29(26,30)21-12(24)8-2-1-4-19-6-8/h1-6,9,11,13,23H,7H2,(H2,18,20,25)(H2,21,24,26,30)/t9-,11-,13-,29?/m1/s1

Standard InChI Key:  HXPYERWZLIDZGR-GGOLNUEHSA-N

Alternative Forms

1. Parent:

   

   ALA3236418

   N-[[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]pyridine-3-carboxamide

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: 463.36

Molecular Weight (Monoisotopic): 463.0527

AlogP: 0.60

#Rotatable Bonds: 6

Polar Surface Area: 158.66

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.14

CX Basic pKa: 3.60

CX LogP: -2.52

CX LogD: -2.34

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: 0.32

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