Phosphoric acid mono-[5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester

ID: ALA603555

Chembl Id: CHEMBL603555

PubChem CID: 46873925

Max Phase: Preclinical

Molecular Formula: C9H12FN2O9P

Molecular Weight: 342.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(=O)n(C2O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]2O)cc1F

Standard InChI:  InChI=1S/C9H12FN2O9P/c10-3-1-12(9(16)11-7(3)15)8-6(14)5(13)4(21-8)2-20-22(17,18)19/h1,4-6,8,13-14H,2H2,(H,11,15,16)(H2,17,18,19)/t4-,5-,6+,8?/m1/s1

Standard InChI Key:  RNBMPPYRHNWTMA-KQTDWGMTSA-N

Alternative Forms

1. Parent:

   

   ALA603555

   [(2R,3S,4S)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate

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: 342.17

Molecular Weight (Monoisotopic): 342.0264

AlogP: -2.60

#Rotatable Bonds: 4

Polar Surface Area: 171.31

Molecular Species: ACID

HBA: 8

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.23

CX Basic pKa: ┄

CX LogP: -2.34

CX LogD: -5.95

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.37

Np Likeness Score: 0.97

References

1. Nakayama C, Wataya Y, Santi DV, Saneyoshi M, Ueda T..  (1981)  Interaction of 1-(5-phospho-beta-D-arabinofuranosyl)-5-substituted-uracils with thymidylate synthetase: mechanism-based inhibition by 1-(5-phospho-beta-D-arabinosyl)-5-fluorouracil.,  24  (10): [PMID:7328576] [10.1021/jm00142a008]

2. Béres J, Bentrude WG, Kálmán A, Párkányi L, Balzarini J, De Clercq E..  (1986)  Synthesis, structure, and antitumor and antiviral activities of a series of 5-halouridine cyclic 3',5'-monophosphates.,  29  (4): [PMID:3007759] [10.1021/jm00154a011]

Source

Source(1):

• Scientific Literature