Benzyl 3-(((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)propanoate

ID: ALA5290307

Chembl Id: CHEMBL5290307

Max Phase: Preclinical

Molecular Formula: C19H20F2N3O8P

Molecular Weight: 487.35

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H20F2N3O8P/c20-19(21)16-13(31-17(19)24-8-6-14(22)23-18(24)26)11-30-33(27,32-16)29-9-7-15(25)28-10-12-4-2-1-3-5-12/h1-6,8,13,16-17H,7,9-11H2,(H2,22,23,26)/t13-,16-,17-,33?/m1/s1

Standard InChI Key:  YRDKHWXAFNAQEP-CVOYYNBSSA-N

Alternative Forms

1. Parent:

   

   ALA5290307

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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: 487.35

Molecular Weight (Monoisotopic): 487.0956

AlogP: 2.03

#Rotatable Bonds: 7

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: 1.27

CX LogD: 1.27

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: 0.32

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