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Fluoroorotic acid

Fluoroorotic acid structure

CAS No:
703-95-7
Formula:
C5H3FN2O4
Chemical Name:
Fluoroorotic acid
Synonyms:
4-Pyrimidinecarboxylic acid,5-fluoro-1,2,3,6-tetrahydro-2,6-dioxo-;Orotic acid,5-fluoro-;5-Fluoro-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid;5-Fluoroorotic acid;Fluoroorotic acid;ENT 26398;NSC 31712;WR 152520;5-Fluoroorotate;NSC 143130;5-Fluoro-2,6-dihydroxypyrimidine-4-carboxylic acid;827-26-9
Categories:
Specialty Chemicals

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Description

White to Off-White Crystalline Solid

Fluoroorotic acid Basic Attributes

Molecular Weight：

174.09

Exact Mass：

174.09

EC Number：

211-876-0

UNII：

7IA9OUC93E

NSC Number：

31712

DSSTox ID：

DTXSID90220573

HScode：

2933599090

Characteristics

PSA：

95.5

XLogP3：

-0.9

Appearance：

white to pale yellow powder

Density：

1.8±0.1 g/cm3

Melting Point：

255 °C (decomp)

Refractive Index：

1.580

Storage Conditions：

-20ºC

Safety Information

wgk germany：

hazard class code：

R22;R36/37/38

safety instructions：

S26-S36

RTECS Number：

UV7800000

Marks：

Xn:Harmful;

Stability/Shelf Life：

Stable under normal shipping and handling conditions.

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

5-fluoroorotic acid

Fluoroorotic acid Use and Manufacturing

5-FOA(5-Fluoroorotic acid ) has become a valuable tool for research in the field of molecular genetics. It has been employed in the selection of resistant strains of Saccharomyces cerevisiae that possess a mutant URA3 gene which renders them orotidine-5'-phosphate decarboxylase deficient. 5-FOA is coverted to 5-fluorouridine monophosphate (5-FUMP) in yeast cells, which can become incorporated into RNA or metabolized to the highly toxic 5-fluoro-2’-deoxyuridine monophosphate (5-FdUMP). 5-FdUMP is a potent inhibitor of thymidylate synthase (TS), causing the cessation of DNA synthesis. More recently, 5-FOA has been shown to possess potent antimalarial activity against both chloroquine-susceptible and chloroquine-resistant clones of Plasmodium falciparum. Studies indicate that TS is the primary target of 5-FOA in malarial parasites. The combination of 5-FOA and uracil has been effective in treating mice infected with Plasmodium yoelli. 5-FOA may also have potential in the treatment of human malarial infections when used in combination with other agents. Useful in the selection of orotidine-5′-phosphate decarboxylase mutants of Saccharomyces cerevisiae.

Computed Properties

Molecular Weight:174.09
XLogP3:-0.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:174.00768474
Monoisotopic Mass:174.00768474
Topological Polar Surface Area:95.5
Heavy Atom Count:12
Complexity:309
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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