Molecule ID: 18343

IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoropyrimidine-2,4-dione

Description: The molecule is a pyrimidine 5'-deoxyribonucleoside that is 5-fluorouridine in which the hydroxy group at the 5' position is replaced by a hydrogen. It is an oral prodrug of the antineoplastic agent 5-fluorouracil. Designed to circumvent the rapid degradation of 5-fluorouracil by dihydropyrimidine dehydrogenase in the gut wall, it is converted into 5-fluorouracil in the presence of pyrimidine nucleoside phosphorylase. It has a role as an antimetabolite, an antineoplastic agent and a prodrug. It is an organofluorine compound and a pyrimidine 5'-deoxyribonucleoside.

SMILES: C[C@H]1O[C@@H](n2cc(F)c(O)nc2=O)[C@H](O)[C@@H]1O

SELFIES: [C][C@H1][O][C@@H1][Branch1][S][N][C][=C][Branch1][C][F][C][Branch1][C][O][=N][C][Ring1][Branch2][=O][C@H1][Branch1][C][O][C@@H1][Ring1][#C][O]

InChI: InChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1

Molecular Properties:
- Polar Surface Area: 99.1 Ų
- LogP: -1.7