Benzyl 5-(((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)pentanoate

ID: ALA5278247

Chembl Id: CHEMBL5278247

Max Phase: Preclinical

Molecular Formula: C21H24F2N3O8P

Molecular Weight: 515.41

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H24F2N3O8P/c22-21(23)18-15(33-19(21)26-10-9-16(24)25-20(26)28)13-32-35(29,34-18)31-11-5-4-8-17(27)30-12-14-6-2-1-3-7-14/h1-3,6-7,9-10,15,18-19H,4-5,8,11-13H2,(H2,24,25,28)/t15-,18-,19-,35?/m1/s1

Standard InChI Key:  LITKZIWTNCLAPC-XUTICSOSSA-N

Alternative Forms

1. Parent:

   

   ALA5278247

   ---

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: 515.41

Molecular Weight (Monoisotopic): 515.1269

AlogP: 2.81

#Rotatable Bonds: 9

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: 2.00

CX LogD: 2.00

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.30

Np Likeness Score: 0.42

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