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

ID: ALA3236426

Chembl Id: CHEMBL3236426

PubChem CID: 90654421

Max Phase: Preclinical

Molecular Formula: C20H24F2N5O8P

Molecular Weight: 531.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](Cc1ccccc1)C(=O)NP(=O)(O)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C(F)(F)[C@@H]1O

Standard InChI:  InChI=1S/C20H24F2N5O8P/c1-11(28)24-13(9-12-5-3-2-4-6-12)17(30)26-36(32,33)34-10-14-16(29)20(21,22)18(35-14)27-8-7-15(23)25-19(27)31/h2-8,13-14,16,18,29H,9-10H2,1H3,(H,24,28)(H2,23,25,31)(H2,26,30,32,33)/t13-,14+,16+,18+/m0/s1

Standard InChI Key:  YGOLOXBHJQGJSJ-GARXJVFOSA-N

Alternative Forms

1. Parent:

   

   ALA3236426

   N-[(2S)-2-acetamido-3-phenylpropanoyl]-[[(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: 531.41

Molecular Weight (Monoisotopic): 531.1331

AlogP: -0.30

#Rotatable Bonds: 9

Polar Surface Area: 195.10

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.52

CX Basic pKa: ┄

CX LogP: -1.06

CX LogD: -3.43

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.27

Np Likeness Score: 0.56

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