{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-2-(hydroxymethyl)oxolan-3-yl]oxy}[2-(benzyloxy)-2-oxoethoxy]phosphinic acid

ID: ALA5267441

Chembl Id: CHEMBL5267441

Max Phase: Preclinical

Molecular Formula: C18H20F2N3O9P

Molecular Weight: 491.34

Names and Identifiers

Canonical SMILES:  Nc1ccn([C@@H]2O[C@H](CO)[C@@H](OP(=O)(O)OCC(=O)OCc3ccccc3)C2(F)F)c(=O)n1

Standard InChI:  InChI=1S/C18H20F2N3O9P/c19-18(20)15(12(8-24)31-16(18)23-7-6-13(21)22-17(23)26)32-33(27,28)30-10-14(25)29-9-11-4-2-1-3-5-11/h1-7,12,15-16,24H,8-10H2,(H,27,28)(H2,21,22,26)/t12-,15-,16-/m1/s1

Standard InChI Key:  YMVILAXKUPEYAS-DAXOMENPSA-N

Alternative Forms

1. Parent:

   

   ALA5267441

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 491.34

Molecular Weight (Monoisotopic): 491.0905

AlogP: 0.60

#Rotatable Bonds: 9

Polar Surface Area: 172.43

Molecular Species: ACID

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.73

CX Basic pKa:

CX LogP: 0.14

CX LogD: -2.24

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.33

Np Likeness Score: 0.56

References

1. Zhang L, Qi K, Xu J, Xing Y, Wang X, Tong L, He Z, Xu W, Li X, Jiang Y..  (2023)  Design, Synthesis, and Anti-Cancer Evaluation of Novel Cyclic Phosphate Prodrug of Gemcitabine.,  66  (6): [PMID:36867101] [10.1021/acs.jmedchem.3c00006]

Source

Source(1):

• Scientific Literature