2'-Deoxy-2',2'-difluoro-D-cytidine-5'-O-[phenyl-(cyclohexoxy-L-alaninyl)]-phosphate

ID: ALA3126003

Chembl Id: CHEMBL3126003

PubChem CID: 76332707

Max Phase: Preclinical

Molecular Formula: C24H31F2N4O8P

Molecular Weight: 572.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NP(=O)(OC[C@H]1O[C@@H](n2ccc(N)nc2=O)C(F)(F)[C@@H]1O)Oc1ccccc1)C(=O)OC1CCCCC1

Standard InChI:  InChI=1S/C24H31F2N4O8P/c1-15(21(32)36-16-8-4-2-5-9-16)29-39(34,38-17-10-6-3-7-11-17)35-14-18-20(31)24(25,26)22(37-18)30-13-12-19(27)28-23(30)33/h3,6-7,10-13,15-16,18,20,22,31H,2,4-5,8-9,14H2,1H3,(H,29,34)(H2,27,28,33)/t15-,18+,20+,22+,39?/m0/s1

Standard InChI Key:  LVHYUTBYVPPDHJ-VKTBRLFESA-N

Alternative Forms

1. Parent:

   

   ALA3126003

   cyclohexyl (2S)-2-[[[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 572.50

Molecular Weight (Monoisotopic): 572.1848

AlogP: 2.78

#Rotatable Bonds: 10

Polar Surface Area: 164.23

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.22

CX Basic pKa:

CX LogP: 2.09

CX LogD: 2.09

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.28

Np Likeness Score: 0.53

References

1. Slusarczyk M, Lopez MH, Balzarini J, Mason M, Jiang WG, Blagden S, Thompson E, Ghazaly E, McGuigan C..  (2014)  Application of ProTide technology to gemcitabine: a successful approach to overcome the key cancer resistance mechanisms leads to a new agent (NUC-1031) in clinical development.,  57  (4): [PMID:24471998] [10.1021/jm401853a]

2. 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