Isopropyl 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: ALA5274649

Chembl Id: CHEMBL5274649

Max Phase: Preclinical

Molecular Formula: C14H18F2N3O8P

Molecular Weight: 425.28

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H18F2N3O8P/c1-7(2)25-10(20)6-24-28(22)23-5-8-11(27-28)14(15,16)12(26-8)19-4-3-9(17)18-13(19)21/h3-4,7-8,11-12H,5-6H2,1-2H3,(H2,17,18,21)/t8-,11-,12-,28?/m1/s1

Standard InChI Key:  JLGSFGOTNBYZBM-WPUNQFSZSA-N

Alternative Forms

1. Parent:

   

   ALA5274649

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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: 425.28

Molecular Weight (Monoisotopic): 425.0800

AlogP: 0.85

#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: 0.08

CX LogD: 0.08

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: 0.30

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