Isopropyl ((((2R,3R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-4,4-difluoro-3-hydroxytetrahydrofuran-2-yl)methoxy)(2-methoxy-2-oxoethoxy)phosphoryl)-L-alaninate

ID: ALA5266526

Chembl Id: CHEMBL5266526

Max Phase: Preclinical

Molecular Formula: C18H27F2N4O10P

Molecular Weight: 528.40

Names and Identifiers

Canonical SMILES:  COC(=O)COP(=O)(N[C@@H](C)C(=O)OC(C)C)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C(F)(F)[C@@H]1O

Standard InChI:  InChI=1S/C18H27F2N4O10P/c1-9(2)33-15(27)10(3)23-35(29,32-8-13(25)30-4)31-7-11-14(26)18(19,20)16(34-11)24-6-5-12(21)22-17(24)28/h5-6,9-11,14,16,26H,7-8H2,1-4H3,(H,23,29)(H2,21,22,28)/t10-,11+,14+,16+,35?/m0/s1

Standard InChI Key:  DYTRDDUHXNTJFT-VQPXBACLSA-N

Alternative Forms

1. Parent:

   

   ALA5266526

   ---

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: 528.40

Molecular Weight (Monoisotopic): 528.1433

AlogP: -0.04

#Rotatable Bonds: 11

Polar Surface Area: 190.53

Molecular Species: NEUTRAL

HBA: 13

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.51

CX Basic pKa:

CX LogP: -0.97

CX LogD: -0.97

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.26

Np Likeness Score: 0.45

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