Isopropyl ((((2R,3R,5R)-4,4-Difluoro-3-hydroxy-5-(2-oxo-4-(2-propylpentanamido)pyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methoxy)(2-methoxy-2-oxoethoxy)phosphoryl)-L-alaninate

ID: ALA5279684

Chembl Id: CHEMBL5279684

Max Phase: Preclinical

Molecular Formula: C26H41F2N4O11P

Molecular Weight: 654.60

Names and Identifiers

Canonical SMILES:  CCCC(CCC)C(=O)Nc1ccn([C@@H]2O[C@H](COP(=O)(N[C@@H](C)C(=O)OC(C)C)OCC(=O)OC)[C@@H](O)C2(F)F)c(=O)n1

Standard InChI:  InChI=1S/C26H41F2N4O11P/c1-7-9-17(10-8-2)22(35)29-19-11-12-32(25(37)30-19)24-26(27,28)21(34)18(43-24)13-40-44(38,41-14-20(33)39-6)31-16(5)23(36)42-15(3)4/h11-12,15-18,21,24,34H,7-10,13-14H2,1-6H3,(H,31,38)(H,29,30,35,37)/t16-,18+,21+,24+,44?/m0/s1

Standard InChI Key:  MCVDHEWYTAUAQV-WVYDSOGVSA-N

Alternative Forms

1. Parent:

   

   ALA5279684

   ---

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: 654.60

Molecular Weight (Monoisotopic): 654.2478

AlogP: 2.54

#Rotatable Bonds: 17

Polar Surface Area: 193.61

Molecular Species: NEUTRAL

HBA: 13

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.11

CX Basic pKa:

CX LogP: 1.98

CX LogD: 1.98

Aromatic Rings: 1

Heavy Atoms: 44

QED Weighted: 0.16

Np Likeness Score: 0.00

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