Basic information
- CAS
703-95-7- Standard SMILES
O=C(O)c1[nH]c(=O)[nH]c(=O)c1F- InChIKey
SEHFUALWMUWDKS-UHFFFAOYSA-N- Molecular formula
- C5H3FN2O4
- Average molar mass
- 174.09 g/mol
- Monoisotopic mass
- 174.00768474
Overview
inhibits the dietary induction of serine dehydratase
Names & identifiers
- Preferred name
- Fluoroorotic acid
- IUPAC
- 5-fluoro-2,4-dioxo-1H-pyrimidine-6-carboxylic acid
- English name
- 5-Fluoroorotic acid
- Molecular formula
- C5H3FN2O4
- Molecular weight
- 174.09
Names & synonyms
5-Fluoroorotic acid703-95-7Fluoroorotic acidOrotic acid, 5-fluoro-ENT-26398NSC 31712Ro 2-99457IA9OUC93E1,2,3,6-Tetrahydro-2,6-dioxo-5-fluoro-4-pyrimidinecarboxylic acidNSC-317125-Fluoro-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acidWR-152520
Show more names
foa5-FOAfoFluoxydin5' FOAro2-9945nsc31712WR 152520
5-FLUORO-6-CARBOXYURACILDTXSID90220573RO-2-9945RefChem:102658CHEBI:74498DTXCID20143064211-876-05-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Database identifiers
- CAS
703-95-7- PubChem CID
- 69711
- DTXSID
DTXSID90220573- ChEMBL
CHEMBL1232805- UNII
- 7IA9OUC93E
- EC Number
Properties
Computed structural properties
- XLogP
- -0.9
- Topological polar surface area
- 95.5 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 309
Experimental & physicochemical properties
SpringerMaterials Properties19F nuclear magnetic resonance spectrum
Physicochemical properties
- Melting point
- 278 °C · 278 °C (dec.)(lit.)
- Boiling point
- 143 °C · 143°C (rough estimate)
- Density
- 1.6154 · 1.6154 (estimate)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- 4 OH · NH4OH 4 M: 50 mg/mL, clear, faintly yellow
- pka
- 2.04 · 2.04±0.20(Predicted)
- form
- solid
- color
- Pale yellow
- Merck
- 14 · 14,4176
- InChI
- InChI=1S/C5H3FN2O4/c6-1-2(4(10)11)7-5(12)8-3(1)9/h(H,10,11)(H2,7,8,9,12)
- InChIKey
- LODRRYMGPWQCTR-UHFFFAOYSA-N
- SMILES
- C1(=O)NC(=O)C(F)=C(C(O)=O)N1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- F
- 10
- wgk
- 3
- rtecs
- UV7800000
- hs_code
- 29335990
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-36-36/37/39-27
- hazard_class
- IRRITANT
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P264-P270-P301+P312+P330-P501-P261-P305+P351+P338
Chemistry & industry
Applications
UsesUseful in the selection of orotidine-5′-phosphate decarboxylase mutants of Saccharomyces cerevisiae.
Uses5-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.
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
Changzhou Carman Chemical Co., Ltd.15061933924
佛山市丽源化工有限公司13889923167 13690318880 · [email protected]
河北创海生物科技有限公司
Related reactions
3 records
Compound notes
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