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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2023-02-21 17:18:14 UTC
HMDB IDHMDB0014684
Secondary Accession Numbers
  • HMDB14684
Metabolite Identification
Common NameFluorouracil
DescriptionFluorouracil is only found in individuals that have used or taken this drug. It is a pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the thymidylate synthetase conversion of deoxyuridylic acid to thymidylic acid. [PubChem]The precise mechanism of action has not been fully determined, but the main mechanism of fluorouracil is thought to be the binding of the deoxyribonucleotide of the drug (FdUMP) and the folate cofactor, N5–10-methylenetetrahydrofolate, to thymidylate synthase (TS) to form a covalently bound ternary complex. This results in the inhibition of the formation of thymidylate from uracil, which leads to the inhibition of DNA and RNA synthesis and cell death. Fluorouracil can also be incorporated into RNA in place of uridine triphosphate (UTP), producing a fraudulent RNA and interfering with RNA processing and protein synthesis.
Structure
Data?1676999894
Synonyms
ValueSource
5-FluoracilChEBI
5-Fluoropyrimidine-2,4-dioneChEBI
5-FUChEBI
FluorouraciloChEBI
FluorouracilumChEBI
5-FluorouracilKegg
AdrucilKegg
CaracKegg
FluoroplexKegg
5-FU medacHMDB
5-Fluorouracil-biosynHMDB
5FUHMDB
Dermatech brand OF fluorouracilHMDB
EfudexHMDB
Fluoro uracile icnHMDB
Fluorouracil gryHMDB
Fluorouracil monopotassium saltHMDB
Neocorp brand OF fluorouracilHMDB
Roche brand OF fluorouracilHMDB
Teva brand OF fluorouracilHMDB
5 FU medacHMDB
5 HU hexalHMDB
5-HU hexalHMDB
Dakota, fluorouracileHMDB
EfudixHMDB
Fluorouracil-gryHMDB
Fluorouracile dakotaHMDB
Haemato brand OF fluorouracilHMDB
Haemato fuHMDB
ICN brand OF fluorouracilHMDB
NeofluorHMDB
5 Fluorouracil biosynHMDB
5-FU lederleHMDB
CSP Brand OF fluorouracilHMDB
Dakota brand OF fluorouracilHMDB
Ferrer brand OF fluorouracilHMDB
Fluoro-uracile icnHMDB
Fluorouracil mononitrateHMDB
Fluorouracil monosodium saltHMDB
Fluorouracil teva brandHMDB
Fluorouracilo ferrer farHMDB
FluracedylHMDB
OnkofluorHMDB
Pharmachemie brand OF fluorouracil monosodium saltHMDB
Biosyn brand OF fluorouracilHMDB
5 FU lederleHMDB
5 FluorouracilHMDB
Allergan brand OF fluorouracilHMDB
Dermik brand OF fluorouracilHMDB
Fluorouracil potassium saltHMDB
FluoruracilHMDB
FlurodexHMDB
Gry brand OF fluorouracilHMDB
Haemato-fuHMDB
Hexal brand OF fluorouracilHMDB
Onkoworks brand OF fluorouracilHMDB
RibofluorHMDB
Riemser brand OF fluorouracilHMDB
Medac brand OF fluorouracilHMDB
Ribosepharm brand OF fluorouracilHMDB
Chemical FormulaC4H3FN2O2
Average Molecular Weight130.0772
Monoisotopic Molecular Weight130.017855555
IUPAC Name5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Namefluorouracil
CAS Registry Number51-21-8
SMILES
FC1=CNC(=O)NC1=O
InChI Identifier
InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChI KeyGHASVSINZRGABV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentHalopyrimidines
Alternative Parents
Substituents
  • Hydroxypyrimidine
  • Halopyrimidine
  • Aryl halide
  • Aryl fluoride
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point280 - 282 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.86 g/LNot Available
LogP-0.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.86 g/LALOGPS
logP-0.58ALOGPS
logP-0.66ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.17 m³·mol⁻¹ChemAxon
Polarizability9.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+121.56830932474
DeepCCS[M-H]-118.4830932474
DeepCCS[M-2H]-154.89430932474
DeepCCS[M+Na]+130.12530932474
AllCCS[M+H]+127.332859911
AllCCS[M+H-H2O]+122.532859911
AllCCS[M+NH4]+131.832859911
AllCCS[M+Na]+133.132859911
AllCCS[M-H]-120.032859911
AllCCS[M+Na-2H]-122.032859911
AllCCS[M+HCOO]-124.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FluorouracilFC1=CNC(=O)NC1=O1916.5Standard polar33892256
FluorouracilFC1=CNC(=O)NC1=O1062.5Standard non polar33892256
FluorouracilFC1=CNC(=O)NC1=O1491.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluorouracil,1TMS,isomer #1C[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O1448.7Semi standard non polar33892256
Fluorouracil,1TMS,isomer #1C[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O1261.8Standard non polar33892256
Fluorouracil,1TMS,isomer #1C[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O1777.3Standard polar33892256
Fluorouracil,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O1389.3Semi standard non polar33892256
Fluorouracil,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O1252.0Standard non polar33892256
Fluorouracil,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O1754.6Standard polar33892256
Fluorouracil,2TMS,isomer #1C[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C)C1=O1613.7Semi standard non polar33892256
Fluorouracil,2TMS,isomer #1C[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C)C1=O1416.4Standard non polar33892256
Fluorouracil,2TMS,isomer #1C[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C)C1=O1652.0Standard polar33892256
Fluorouracil,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O1730.2Semi standard non polar33892256
Fluorouracil,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O1458.0Standard non polar33892256
Fluorouracil,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)[NH]C1=O1896.8Standard polar33892256
Fluorouracil,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O1623.6Semi standard non polar33892256
Fluorouracil,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O1449.9Standard non polar33892256
Fluorouracil,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(F)C1=O1849.9Standard polar33892256
Fluorouracil,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C1=O1943.5Semi standard non polar33892256
Fluorouracil,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C1=O1820.7Standard non polar33892256
Fluorouracil,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=C(F)C(=O)N([Si](C)(C)C(C)(C)C)C1=O1881.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Fluorouracil EI-B (Non-derivatized)splash10-001i-9800000000-a3301f9fea9145d074802017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorouracil CI-B (Non-derivatized)splash10-001i-0900000000-76691bd3cba2765d36872017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorouracil CI-B (Non-derivatized)splash10-001i-0900000000-d801d8209e9a5aa4830b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorouracil CI-B (Non-derivatized)splash10-0002-0900000000-7521695ae4a96b4a5a982017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorouracil EI-B (Non-derivatized)splash10-001i-9800000000-a3301f9fea9145d074802018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorouracil CI-B (Non-derivatized)splash10-001i-0900000000-76691bd3cba2765d36872018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorouracil CI-B (Non-derivatized)splash10-001i-0900000000-d801d8209e9a5aa4830b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Fluorouracil CI-B (Non-derivatized)splash10-0002-0900000000-7521695ae4a96b4a5a982018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluorouracil GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9600000000-8c2b278c2716f3e6b27c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fluorouracil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9400000000-b8247c8f5c45b12efaa62014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-c639ed1b5365f368b59c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-1a7a70df49a360e1458c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-d89f2d944fe1cac39f552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-50b33770c08680863cf62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-cd5bef421a05073cb1f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-3900000000-ec9c9e1dfc9a16f625a22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-df98a4532ca49a0a04362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-50b33770c08680863cf62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-50b33770c08680863cf62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-df98a4532ca49a0a04362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-b117f5fa58c8f98b5c152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , negative-QTOFsplash10-0a4i-9000000000-f3e71a41b6d4417d33fd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOFsplash10-001i-9200000000-29362607b7c48b82973c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-693d492f316b0c7d5ed52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOFsplash10-001i-1900000000-0c0ee9469bf49688c5d22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOFsplash10-001i-1900000000-0cecca0d265e958e19d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOFsplash10-03e9-1900000000-46f20f71dbc96630cee72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOFsplash10-03di-1900000000-4330f38956afe6c476362017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fluorouracil LC-ESI-ITFT , positive-QTOFsplash10-03di-2900000000-f935071622b89177697b2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorouracil 10V, Positive-QTOFsplash10-001i-1900000000-3fa9b91447db7dc7ba772015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorouracil 20V, Positive-QTOFsplash10-01q9-9800000000-32bf878787078ce9d8172015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorouracil 40V, Positive-QTOFsplash10-03di-9000000000-3ef559051a5b99c94b292015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorouracil 10V, Negative-QTOFsplash10-004i-4900000000-82764fbca3290816328d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorouracil 20V, Negative-QTOFsplash10-000f-9100000000-2da5eb3c925c027b50222015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fluorouracil 40V, Negative-QTOFsplash10-0006-9000000000-1cf432837297c55833a52015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00544 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00544 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00544
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3268
KEGG Compound IDC07649
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluorouracil
METLIN IDNot Available
PubChem Compound3385
PDB IDNot Available
ChEBI ID46345
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Longley DB, Harkin DP, Johnston PG: 5-fluorouracil: mechanisms of action and clinical strategies. Nat Rev Cancer. 2003 May;3(5):330-8. [PubMed:12724731 ]
  2. Petty RD, Cassidy J: Novel fluoropyrimidines: improving the efficacy and tolerability of cytotoxic therapy. Curr Cancer Drug Targets. 2004 Mar;4(2):191-204. [PubMed:15032669 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
P42898
Molecular weight:
74595.895
References
  1. Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. doi: 10.2217/pgs.10.167. [PubMed:21332317 ]
General function:
Involved in electron carrier activity
Specific function:
Involved in pyrimidine base degradation. Catalyzes the reduction of uracil and thymine. Also involved the degradation of the chemotherapeutic drug 5-fluorouracil.
Gene Name:
DPYD
Uniprot ID:
Q12882
Molecular weight:
111400.32
Reactions
Fluorouracil + NADPH + Hydrogen Ion → 5,6-Dihydro-5-fluorouracil + NADPdetails
References
  1. Ho DH, Townsend L, Luna MA, Bodey GP: Distribution and inhibition of dihydrouracil dehydrogenase activities in human tissues using 5-fluorouracil as a substrate. Anticancer Res. 1986 Jul-Aug;6(4):781-4. [PubMed:3752956 ]
  2. Keizer HJ, De Bruijn EA, Tjaden UR, De Clercq E: Inhibition of fluorouracil catabolism in cancer patients by the antiviral agent (E)-5-(2-bromovinyl)-2'-deoxyuridine. J Cancer Res Clin Oncol. 1994;120(9):545-9. [PubMed:8045919 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
UMPS
Uniprot ID:
P11172
Molecular weight:
52221.075
Reactions
Fluorouracil + Phosphoribosyl pyrophosphate → 5-Fluorouridine monophosphate + Pyrophosphatedetails
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
May have a role in maintaining the integrity of the blood vessels. Has growth promoting activity on endothelial cells, angiogenic activity in vivo and chemotactic activity on endothelial cells in vitro. Catalyzes the reversible phosphorolysis of thymidine. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:
TYMP
Uniprot ID:
P19971
Molecular weight:
49954.965
Reactions
5'-Deoxy-5-fluorouridine + Phosphate → Fluorouracil + 5-Deoxyribose-1-phosphatedetails
Fluorouracil + Deoxyribose 1-phosphate → Floxuridine + Phosphatedetails
References
  1. Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. doi: 10.2217/pgs.10.167. [PubMed:21332317 ]
General function:
Involved in thymidylate synthase activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
P04818
Molecular weight:
35715.65
References
  1. Formentini A, Sander S, Denzer S, Straeter J, Henne-Bruns D, Kornmann M: Thymidylate synthase expression in resectable and unresectable pancreatic cancer: role as predictive or prognostic marker? Int J Colorectal Dis. 2007 Jan;22(1):49-55. Epub 2006 Mar 15. [PubMed:16538493 ]
  2. Huang CL, Yokomise H, Fukushima M, Kinoshita M: Tailor-made chemotherapy for non-small cell lung cancer patients. Future Oncol. 2006 Apr;2(2):289-99. [PubMed:16563096 ]
  3. Fernandez-Contreras ME, Sanchez-Prudencio S, Sanchez-Hernandez JJ, Garcia de Paredes ML, Gisbert JP, Roda-Navarro P, Gamallo C: Thymidylate synthase expression pattern, expression level and single nucleotide polymorphism are predictors for disease-free survival in patients of colorectal cancer treated with 5-fluorouracil. Int J Oncol. 2006 May;28(5):1303-10. [PubMed:16596248 ]
  4. Garcia V, Garcia JM, Pena C, Silva J, Dominguez G, Hurtado A, Alonso I, Rodriguez R, Provencio M, Bonilla F: Thymidylate synthase messenger RNA expression in plasma from patients with colon cancer: prognostic potential. Clin Cancer Res. 2006 Apr 1;12(7 Pt 1):2095-100. [PubMed:16609021 ]
  5. Ploylearmsaeng SA, Fuhr U, Jetter A: How may anticancer chemotherapy with fluorouracil be individualised? Clin Pharmacokinet. 2006;45(6):567-92. [PubMed:16719540 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Rustum YM: Thymidylate synthase: a critical target in cancer therapy? Front Biosci. 2004 Sep 1;9:2467-73. [PubMed:15353299 ]
  8. Scartozzi M, Maccaroni E, Giampieri R, Pistelli M, Bittoni A, Del Prete M, Berardi R, Cascinu S: 5-Fluorouracil pharmacogenomics: still rocking after all these years? Pharmacogenomics. 2011 Feb;12(2):251-65. doi: 10.2217/pgs.10.167. [PubMed:21332317 ]
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1-phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis.
Gene Name:
UPP1
Uniprot ID:
Q16831
Molecular weight:
33934.005
Reactions
Fluorouracil + Ribose 1-phosphate → 5-Fluorouridine + Phosphatedetails
References
  1. Yan R, Wan L, Pizzorno G, Cao D: Uridine phosphorylase in breast cancer: a new prognostic factor? Front Biosci. 2006 Sep 1;11:2759-66. [PubMed:16720348 ]

Only showing the first 10 proteins. There are 11 proteins in total.