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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:59:31 UTC
Update Date2021-09-14 15:39:00 UTC
HMDB IDHMDB0060397
Secondary Accession Numbers
  • HMDB60397
Metabolite Identification
Common Name5-Fluorouridine monophosphate
Description5-Fluorouridine monophosphate is a metabolite of fluorouracil. Fluorouracil (5-FU or f5U) (sold under the brand names Adrucil, Carac, Efudix, Efudex and Fluoroplex) is a drug that is a pyrimidine analog which is used in the treatment of cancer. It is a suicide inhibitor and works through irreversible inhibition of thymidylate synthase. It belongs to the family of drugs called antimetabolites. It is typically administered with leucovorin. (Wikipedia)
Structure
Data?1563866055
Synonyms
ValueSource
5-F-UMPChEBI
5-Fluorouridylic acidChEBI
FosfluoridineChEBI
Fump-5'ChEBI
5-FluorouridylateGenerator
5-Fluorouridine monophosphoric acidGenerator
5-Fluorouridine 5'-monophosphoric acidHMDB
5-Fluorouridine 5'-phosphateHMDB
5-Fluorouridine 5'-phosphate, 18F-labeledHMDB
5'-FUMPHMDB
5-Fluorouridine 5'-phosphate, disodium saltHMDB
5-Fluorouridine 5'-phosphate, calcium saltHMDB
5-Fluorouridine monophosphateChEBI
Chemical FormulaC9H12FN2O9P
Average Molecular Weight342.1717
Monoisotopic Molecular Weight342.026444709
IUPAC Name{[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O
InChI Identifier
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
InChI KeyRNBMPPYRHNWTMA-UAKXSSHOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentPyrimidine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Halopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Aryl fluoride
  • Pyrimidine
  • Aryl halide
  • Phosphoric acid ester
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Urea
  • Secondary alcohol
  • 1,2-diol
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organohalogen compound
  • Organofluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.4 g/LALOGPS
logP-1.3ALOGPS
logP-2.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.64 m³·mol⁻¹ChemAxon
Polarizability26.76 ųChemAxon
Number of Rings2ChemAxon
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]+169.16630932474
DeepCCS[M-H]-166.77130932474
DeepCCS[M-2H]-200.30430932474
DeepCCS[M+Na]+175.25330932474
AllCCS[M+H]+171.532859911
AllCCS[M+H-H2O]+168.532859911
AllCCS[M+NH4]+174.332859911
AllCCS[M+Na]+175.132859911
AllCCS[M-H]-165.232859911
AllCCS[M+Na-2H]-165.032859911
AllCCS[M+HCOO]-164.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Fluorouridine monophosphateO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O3803.7Standard polar33892256
5-Fluorouridine monophosphateO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O2160.7Standard non polar33892256
5-Fluorouridine monophosphateO[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O2941.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Fluorouridine monophosphate,1TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O2590.7Semi standard non polar33892256
5-Fluorouridine monophosphate,1TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=C(F)C(O)=NC1=O2577.7Semi standard non polar33892256
5-Fluorouridine monophosphate,1TMS,isomer #3C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1F2626.8Semi standard non polar33892256
5-Fluorouridine monophosphate,1TMS,isomer #4C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=C(F)C(O)=NC2=O)[C@H](O)[C@@H]1O2745.5Semi standard non polar33892256
5-Fluorouridine monophosphate,2TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F2581.8Semi standard non polar33892256
5-Fluorouridine monophosphate,2TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C2540.9Semi standard non polar33892256
5-Fluorouridine monophosphate,2TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O2698.9Semi standard non polar33892256
5-Fluorouridine monophosphate,2TMS,isomer #4C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F2565.3Semi standard non polar33892256
5-Fluorouridine monophosphate,2TMS,isomer #5C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=C(F)C(O)=NC1=O2692.6Semi standard non polar33892256
5-Fluorouridine monophosphate,2TMS,isomer #6C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O)C=C1F2707.3Semi standard non polar33892256
5-Fluorouridine monophosphate,2TMS,isomer #7C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=C(F)C(O)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C2751.0Semi standard non polar33892256
5-Fluorouridine monophosphate,3TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F2548.0Semi standard non polar33892256
5-Fluorouridine monophosphate,3TMS,isomer #2C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F2691.3Semi standard non polar33892256
5-Fluorouridine monophosphate,3TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C2667.8Semi standard non polar33892256
5-Fluorouridine monophosphate,3TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O2727.6Semi standard non polar33892256
5-Fluorouridine monophosphate,3TMS,isomer #5C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F2685.5Semi standard non polar33892256
5-Fluorouridine monophosphate,3TMS,isomer #6C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@H]1N1C=C(F)C(O)=NC1=O2728.3Semi standard non polar33892256
5-Fluorouridine monophosphate,3TMS,isomer #7C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O)C=C1F2736.9Semi standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F2688.1Semi standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F2669.6Standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F3333.4Standard polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #2C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F2733.6Semi standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #2C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F2674.0Standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #2C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C1F3173.6Standard polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C2721.0Semi standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C2605.5Standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C3168.3Standard polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #4C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F2727.0Semi standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #4C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F2679.3Standard non polar33892256
5-Fluorouridine monophosphate,4TMS,isomer #4C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C1F3203.2Standard polar33892256
5-Fluorouridine monophosphate,5TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F2732.1Semi standard non polar33892256
5-Fluorouridine monophosphate,5TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F2659.9Standard non polar33892256
5-Fluorouridine monophosphate,5TMS,isomer #1C[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1F3034.0Standard polar33892256
5-Fluorouridine monophosphate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O2875.1Semi standard non polar33892256
5-Fluorouridine monophosphate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=C(F)C(O)=NC1=O2859.4Semi standard non polar33892256
5-Fluorouridine monophosphate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1F2864.1Semi standard non polar33892256
5-Fluorouridine monophosphate,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=C(F)C(O)=NC2=O)[C@H](O)[C@@H]1O2988.8Semi standard non polar33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F3059.1Semi standard non polar33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3047.4Semi standard non polar33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O3167.2Semi standard non polar33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3040.4Semi standard non polar33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=C(F)C(O)=NC1=O3155.4Semi standard non polar33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C1F3159.5Semi standard non polar33892256
5-Fluorouridine monophosphate,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=C(F)C(O)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3211.1Semi standard non polar33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3271.5Semi standard non polar33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F3358.4Semi standard non polar33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3336.6Semi standard non polar33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O3384.9Semi standard non polar33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3343.2Semi standard non polar33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=C(F)C(O)=NC1=O3374.2Semi standard non polar33892256
5-Fluorouridine monophosphate,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C1F3384.2Semi standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3546.9Semi standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3400.4Standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3563.0Standard polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F3583.2Semi standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F3370.9Standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1F3453.2Standard polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3560.9Semi standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3333.1Standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=C(F)C(O)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3466.7Standard polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3568.8Semi standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3372.8Standard non polar33892256
5-Fluorouridine monophosphate,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1F3482.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Fluorouridine monophosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9501000000-6e3e3f07071a4b3fe25b2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Fluorouridine monophosphate GC-MS (3 TMS) - 70eV, Positivesplash10-000b-9422320000-a9309e7224043db6e96e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Fluorouridine monophosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 10V, Positive-QTOFsplash10-001i-0901000000-3b46c2e15a4da2f0d7ba2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 20V, Positive-QTOFsplash10-001i-1900000000-5e082b9fb7ff4e4a3bef2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 40V, Positive-QTOFsplash10-0f89-3900000000-95bf4479fa01e01b5fd92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 10V, Negative-QTOFsplash10-004i-6932000000-83f85ee655c0c86555da2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 20V, Negative-QTOFsplash10-004i-9200000000-3d9058daaa7d559c901e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 40V, Negative-QTOFsplash10-004i-9000000000-4b472f80502ae0db304e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 10V, Positive-QTOFsplash10-00ke-0896000000-36a39434e942710b455a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 20V, Positive-QTOFsplash10-0032-0790000000-7f1ccf28f980f99eaf642021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 40V, Positive-QTOFsplash10-000t-8910000000-eea690d5bc86a0096c852021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 10V, Negative-QTOFsplash10-0006-3309000000-dd2203c1062e091c9f1f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 20V, Negative-QTOFsplash10-004i-9300000000-1b995bb274a6141e33b72021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Fluorouridine monophosphate 40V, Negative-QTOFsplash10-004i-9200000000-ec60836b4f08807545272021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16634
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound150856
PDB ID5FU
ChEBI ID40101
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. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Molecular weight:
22760.43
Reactions
5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADPdetails
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 ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Molecular weight:
29298.92
Reactions
5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADPdetails
General function:
Involved in ATP binding
Specific function:
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Molecular weight:
59465.77
Reactions
5-Fluorouridine + Adenosine triphosphate → 5-Fluorouridine monophosphate + ADPdetails