2',2'-Difluoro-2'-deoxycytidine-5'-O-[N-(acetyl)]thiophosphoramidate

ID: ALA3236419

Chembl Id: CHEMBL3236419

PubChem CID: 90654414

Max Phase: Preclinical

Molecular Formula: C11H15F2N4O6PS

Molecular Weight: 400.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)NP(=O)(S)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C(F)(F)[C@@H]1O

Standard InChI:  InChI=1S/C11H15F2N4O6PS/c1-5(18)16-24(21,25)22-4-6-8(19)11(12,13)9(23-6)17-3-2-7(14)15-10(17)20/h2-3,6,8-9,19H,4H2,1H3,(H2,14,15,20)(H2,16,18,21,25)/t6-,8-,9-,24?/m1/s1

Standard InChI Key:  HEOVRPBHXWKFSZ-PBBASEOCSA-N

Alternative Forms

1. Parent:

   

   ALA3236419

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

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: 400.30

Molecular Weight (Monoisotopic): 400.0418

AlogP: -0.09

#Rotatable Bonds: 5

Polar Surface Area: 145.77

Molecular Species: ACID

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.19

CX Basic pKa: ┄

CX LogP: -1.43

CX LogD: -2.97

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.40

Np Likeness Score: 0.79

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