benzyl 2-[[(2S,4aR,6R,7aR)-6-(4-amino-2-oxo-pyrimidin-1-yl)-7,7-difluoro-2-oxo-4,4a,6,7a-tetrahydrofuro[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxy]acetate

ID: ALA5289380

Chembl Id: CHEMBL5289380

Max Phase: Preclinical

Molecular Formula: C18H18F2N3O8P

Molecular Weight: 473.33

Names and Identifiers

Canonical SMILES:  Nc1ccn([C@@H]2O[C@@H]3CO[P@@](=O)(OCC(=O)OCc4ccccc4)O[C@H]3C2(F)F)c(=O)n1

Standard InChI:  InChI=1S/C18H18F2N3O8P/c19-18(20)15-12(30-16(18)23-7-6-13(21)22-17(23)25)9-28-32(26,31-15)29-10-14(24)27-8-11-4-2-1-3-5-11/h1-7,12,15-16H,8-10H2,(H2,21,22,25)/t12-,15-,16-,32+/m1/s1

Standard InChI Key:  OEUXWUMMRHBRLF-ISELOYHASA-N

Alternative Forms

1. Parent:

   

   ALA5289380

   ---

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: 473.33

Molecular Weight (Monoisotopic): 473.0800

AlogP: 1.64

#Rotatable Bonds: 6

Polar Surface Area: 141.20

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.03

CX LogD: 1.03

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.49

Np Likeness Score: 0.29

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