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

ID: ALA3236420

Chembl Id: CHEMBL3236420

PubChem CID: 90654415

Max Phase: Preclinical

Molecular Formula: C16H22F2N5O7PS

Molecular Weight: 497.42

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H22F2N5O7PS/c1-8(24)22-5-2-3-9(22)13(26)21-31(28,32)29-7-10-12(25)16(17,18)14(30-10)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)(H2,21,26,28,32)/t9-,10+,12+,14+,31?/m0/s1

Standard InChI Key:  CROHQJHAAKYLMZ-VPLMXIHASA-N

Alternative Forms

1. Parent:

   

   ALA3236420

   (2S)-1-acetyl-N-[[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphinothioyl]pyrrolidine-2-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: 497.42

Molecular Weight (Monoisotopic): 497.0946

AlogP: -0.10

#Rotatable Bonds: 6

Polar Surface Area: 166.08

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.19

CX Basic pKa: ┄

CX LogP: -1.69

CX LogD: -3.24

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: 0.36

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