Benzyl ((((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: ALA5282964

Chembl Id: CHEMBL5282964

Max Phase: Preclinical

Molecular Formula: C22H27F2N4O10P

Molecular Weight: 576.45

Names and Identifiers

Canonical SMILES:  COC(=O)COP(=O)(N[C@@H](C)C(=O)OCc1ccccc1)OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C(F)(F)[C@@H]1O

Standard InChI:  InChI=1S/C22H27F2N4O10P/c1-13(19(31)35-10-14-6-4-3-5-7-14)27-39(33,37-12-17(29)34-2)36-11-15-18(30)22(23,24)20(38-15)28-9-8-16(25)26-21(28)32/h3-9,13,15,18,20,30H,10-12H2,1-2H3,(H,27,33)(H2,25,26,32)/t13-,15+,18+,20+,39?/m0/s1

Standard InChI Key:  KWGVSYUVDDKLKQ-BDIGAZSHSA-N

Alternative Forms

1. Parent:

   

   ALA5282964

   ---

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: 576.45

Molecular Weight (Monoisotopic): 576.1433

AlogP: 0.75

#Rotatable Bonds: 12

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: -0.02

CX LogD: -0.02

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.24

Np Likeness Score: 0.37

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