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Natural Product (NP) Details

General Information of the NP (ID: NP6495)
Name
Fluoroorotic acid
Synonyms
5-Fluoroorotic acid; 703-95-7; 5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid; 5-Fluoroorotate; Fluoroorotic acid; Orotic acid, 5-fluoro-; 5-Fluorouracil-4-carboxylic acid; 5-FOA; ENT-26398; NSC 31712; Ro 2-9945; UNII-7IA9OUC93E; WR 152520; MLS000737636; 5-fluoro-2,4-dioxo-1H-pyrimidine-6-carboxylic acid; 4-Pyrimidinecarboxylic acid, 5-fluoro-1,2,3,6-tetrahydro-2,6-dioxo-; 7IA9OUC93E; Fluoroorotic Acid, Ultra Pure; FOA; 5-Fluorouracil-6-carboxylic Acid; 1,2,3,6-Tetrahydro-2,6-dioxo-5-fluoro-4-pyrimidinecarboxylic acid; MFCD00042526; SMR000393806; 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-5-fluoro-; 5-Fluoro orotic acid; 5-Fluoroorotic acid (VAN); EINECS 211-876-0; 5-fluoro-2,6-dioxo-1,3-dihydropyrimidine-4-carboxylic acid; AI3-26398; 5-Fluoroortic acid; FOT; 174.09 (anhydrous); C5H3FN2O4.xH2O; 5-Fluoroorotic acid;5-FOA; SCHEMBL44527; WLN: T6VMVMJ EVQ FF; cid_69711; CHEMBL1232805; BDBM47470; 5-Fluoroorotic acid, 98.0%+; DTXSID90220573; 5-fluorouracil-4-carboxylic acid;; HMS2759G19; ACT03077; EBD39533; NSC31712; ZINC1663959; 5-Fluoro-1,2,3,6-tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid; ANW-46244; NSC-31712; SBB066881; AKOS005207200; CS-W017535; 4-Pyrimidinecarboxylic acid, 5-fluoro-1,2,3,6-tetrahydro-2,6-dioxo-, monohydrate; 5-Fluorouracil-4-carboxylic acid hydrate; NCGC00246927-01; Orotic acid, 5-fluoro- (VAN) (8CI); AC-10068; AS-14168; K187; SY001827; AB0014081; F0382; FT-0620427; ST50405211; F-6300; M-2738; 45988-EP2298735A1; 45988-EP2311807A1; 703F957; 2,6-Dihydroxy-5-fluoropyrimidine-4-carboxylic acid; 5-fluoro-2,4-diketo-1H-pyrimidine-6-carboxylic acid; Q18207160; 1,3,6-Tetrahydro-2,6-dioxo-5-fluoro-4-pyrimidinecarboxylic acid; 4-Pyrimidinecarboxylic acid,2,3,6-tetrahydro-2,6-dioxo-5-fluoro-; 5-fluoranyl-2,4-bis(oxidanylidene)-1H-pyrimidine-6-carboxylic acid; 5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydro-4-pyrimidinecarboxylic acid; 5-Fluoro-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid; 4-Pyrimidinecarboxylic acid, 5-fluoro-1,2,3,6-tetrahydro-2,6-dioxo- (9CI)
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Species Origin Homo sapiens ...     Click to Show/Hide
Homo sapiens
Kingdom: Metazoa
Phylum: Chordata
Class: Mammalia
Order: Primates
Family: Hominidae
Genus: Homo
Species: Homo sapiens
Disease Aspergillosis [ICD-11: 1F20] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C5H3FN2O4
PubChem CID
69711
Canonical SMILES
C1(=C(NC(=O)NC1=O)C(=O)O)F
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
SEHFUALWMUWDKS-UHFFFAOYSA-N
CAS Number
CAS 703-95-7
TTD Drug ID
D0E2WX
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Uftoral + Oxaliplatin     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model HT-29 CVCL_0320 Colon adenocarcinoma Homo sapiens
                    In-vivo Model Human colorectal HT29 cell xenografts (1*106 cells) were transplanted s.c. into the hind limb of each animal (Female BALB/c nude mice (nu+/nu+) aged 6 weeks).
                    Experimental
                    Result(s)
Combined treatment (UFT/FA+oxaliplatin) reduced tumor weight by 39% compared to oxaliplatin alone (p<0.05) or UFT/FA (p<0.05).
          Oxaliplatin + 5-fluorouracil     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)
Combination chemotherapy with oxaliplatin, 5-FU, and FA is an active and well-tolerated regimen as first-line treatment in patients with metastatic or recurrent gastric cancer.
          Cisplatin + 5-fluorouracil     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Experimental
                    Result(s)
Weekly administration of 5-FU/FA/cisplatin is an active and well-tolerated regimen. Toxicity is manageable and allows chemotherapy on an outpatient basis without hydration program as required when cisplatin is used at the dose of 50 mg/m2.
          Raltitrexed + 5-fluorouracil     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model LoVo CVCL_0399 Colon adenocarcinoma Homo sapiens
HT-29 CVCL_0320 Colon adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)
Histone deacetylase inhibitor NVP-LAQ824 sensitizes human nonsmall cell lung cancer to the cytotoxic effects of ionizing radiation.
          Methioninase + 5-fluorouracil     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model CCRF-CEM CVCL_0207 T acute lymphoblastic leukemia Homo sapiens
                    Experimental
                    Result(s)
Methioninase in combination with 5-fluorouracil and folinic acid showed cytotoxic synergism in CCRF-CEM.
Target and Pathway
Target(s) Plasmodium dihydroorotase (Malaria dho)  Molecule Info  [7]
Plasmodium dihydroorotate dehydrogenase (Malaria DHOdehase)  Molecule Info  [7]
KEGG Pathway Pyrimidine metabolism Click to Show/Hide
2 Metabolic pathways
Pathwhiz Pathway Pyrimidine Metabolism Click to Show/Hide
Reactome Pyrimidine biosynthesis Click to Show/Hide
WikiPathways Metabolism of nucleotides Click to Show/Hide
References
Reference 1 Antifungal Siderophore Conjugates for Theranostic Applications in Invasive Pulmonary Aspergillosis Using Low-Molecular TAFC Scaffolds. J Fungi (Basel). 2021 Jul 14;7(7):558.
Reference 2 Synergistic antitumoral activity of combined UFT, folinic acid and oxaliplatin against human colorectal HT29 cell xenografts in athymic nude mice. Anticancer Drugs. 2000 Aug;11(7):579-82.
Reference 3 Efficacy and safety of oxaliplatin, 5-Fluorouracil, and folinic Acid combination chemotherapy as first-line treatment in metastatic or recurrent gastric cancer. Cancer Res Treat. 2011 Sep;43(3):154-9.
Reference 4 Treatment of advanced digestive non-colon cancer with a weekly 24-h infusion of high-dose 5-fluorouracil modulated by folinic acid and cisplatin: an easy-to-use and well-tolerated combination. Anticancer Drugs. 2004 Aug;15(7):725-8.
Reference 5 Histone deacetylase inhibitor NVP-LAQ824 sensitizes human nonsmall cell lung cancer to the cytotoxic effects of ionizing radiation. Anticancer Drugs. 2007 Aug;18(7):793-800.
Reference 6 Cytotoxic synergism of methioninase in combination with 5-fluorouracil and folinic acid. Biochem Pharmacol. 2001 Apr 1;61(7):867-76.
Reference 7 Antimalarial activity of orotate analogs that inhibit dihydroorotase and dihydroorotate dehydrogenase. Biochem Pharmacol. 1992 Mar 17;43(6):1295-301.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China