Ethyl 2-(((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)acetate

ID: ALA5283380

Chembl Id: CHEMBL5283380

Max Phase: Preclinical

Molecular Formula: C13H16F2N3O8P

Molecular Weight: 411.25

Names and Identifiers

Canonical SMILES:  CCOC(=O)COP1(=O)OC[C@H]2O[C@@H](n3ccc(N)nc3=O)C(F)(F)[C@@H]2O1

Standard InChI:  InChI=1S/C13H16F2N3O8P/c1-2-22-9(19)6-24-27(21)23-5-7-10(26-27)13(14,15)11(25-7)18-4-3-8(16)17-12(18)20/h3-4,7,10-11H,2,5-6H2,1H3,(H2,16,17,20)/t7-,10-,11-,27?/m1/s1

Standard InChI Key:  GIGPEYLQONPNSS-KAFSKBSVSA-N

Alternative Forms

1. Parent:

   

   ALA5283380

   ---

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: 411.25

Molecular Weight (Monoisotopic): 411.0643

AlogP: 0.46

#Rotatable Bonds: 5

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: -0.33

CX LogD: -0.33

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: 0.40

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