Benzyl 4-(((4aR,6R,7aR)-6-(4-Amino-2-oxopyrimidin-1(2H)-yl)-7,7-difluoro-2-oxidotetrahydro-4H-furo[3,2-d][1,3,2]-dioxaphosphinin-2-yl)oxy)butanoate

ID: ALA5270171

Chembl Id: CHEMBL5270171

Max Phase: Preclinical

Molecular Formula: C20H22F2N3O8P

Molecular Weight: 501.38

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H22F2N3O8P/c21-20(22)17-14(32-18(20)25-9-8-15(23)24-19(25)27)12-31-34(28,33-17)30-10-4-7-16(26)29-11-13-5-2-1-3-6-13/h1-3,5-6,8-9,14,17-18H,4,7,10-12H2,(H2,23,24,27)/t14-,17-,18-,34?/m1/s1

Standard InChI Key:  RIUKJTINHCWZNA-IISQBZAISA-N

Alternative Forms

1. Parent:

   

   ALA5270171

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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: 501.38

Molecular Weight (Monoisotopic): 501.1113

AlogP: 2.42

#Rotatable Bonds: 8

Polar Surface Area: 141.20

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.56

CX LogD: 1.56

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.33

Np Likeness Score: 0.37

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