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

ID: ALA3236425

Chembl Id: CHEMBL3236425

PubChem CID: 90654420

Max Phase: Preclinical

Molecular Formula: C16H22F2N5O8P

Molecular Weight: 481.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCC[C@H]1C(=O)NP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C(F)(F)[C@@H]1O

Standard InChI:  InChI=1S/C16H22F2N5O8P/c1-8(24)22-5-2-3-9(22)13(26)21-32(28,29)30-7-10-12(25)16(17,18)14(31-10)23-6-4-11(19)20-15(23)27/h4,6,9-10,12,14,25H,2-3,5,7H2,1H3,(H2,19,20,27)(H2,21,26,28,29)/t9-,10+,12+,14+/m0/s1

Standard InChI Key:  BYIWQHXWSPDYKJ-UZWIWUQPSA-N

Alternative Forms

1. Parent:

   

   ALA3236425

   N-[(2S)-1-acetylpyrrolidine-2-carbonyl]-[[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy]phosphonamidic 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: 481.35

Molecular Weight (Monoisotopic): 481.1174

AlogP: -1.04

#Rotatable Bonds: 6

Polar Surface Area: 186.31

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.52

CX Basic pKa: ┄

CX LogP: -2.44

CX LogD: -4.82

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.37

Np Likeness Score: 0.47

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