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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:24:27 UTC
HMDB IDHMDB0000469
Secondary Accession Numbers
  • HMDB00469
Metabolite Identification
Common Name5-Hydroxymethyluracil
Description5-Hydroxymethyluracil (5hmU), also known as alpha-hydroxythymine, belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. 5hmU has been identified as a thymine base modification found in the genomes of a diverse range of organisms (PMID: 28137275 ). 5-hydroxymethyluracil has been detected in bacteriophages, dinoflagellates, leishmania, and in eukaryotic genomes where its level appears to be cell type-specific. 5-Hydroxymethyluracil arises from the oxidation of thymine. 5-Hydroxymethyluracil is produced by the enzyme thymine dioxygenase (EC 1.14.11.6) which catalyzes the chemical reaction thymine + 2-oxoglutarate + O2 <-> 5-hydroxymethyluracil + succinate + CO2. The 3 substrates of this enzyme are thymine, 2-oxoglutarate, and O2, whereas its 3 products are 5-hydroxymethyluracil, succinate, and CO2. The 5hmU base can also be generated by oxidation/hydroxylation of thymine by the Ten-Eleven-Translocation (TET) proteins or result from deamination of 5hmC (PMID: 29184924 ). DNA containing 5hmU has been reported to be more flexible and hydrophilic (PMID: 29184924 ).
Structure
Data?1582752133
Synonyms
ValueSource
5-(Hydroxymethyl)-2,4(1H,3H)-pyrimidinedioneChEBI
5-(Hydroxymethyl)uracilChEBI
5-HYDROXYMETHYL uracilChEBI
5-(Hydroxymethyl)-1,3-dihydropyrimidine-2,4-dioneHMDB
a-HydroxythymineHMDB
alpha-HydroxythymineHMDB
HydroxymethyluracilHMDB
Chemical FormulaC5H6N2O3
Average Molecular Weight142.1127
Monoisotopic Molecular Weight142.037842068
IUPAC Name5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional Name5-hydroxymethyluracil
CAS Registry Number4433-40-3
SMILES
OCC1=CNC(=O)NC1=O
InChI Identifier
InChI=1S/C5H6N2O3/c8-2-3-1-6-5(10)7-4(3)9/h1,8H,2H2,(H2,6,7,9,10)
InChI KeyJDBGXEHEIRGOBU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. 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 ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Hydropyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Lactam
  • Urea
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility44 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker124.49930932474
[M-H]-MetCCS_train_neg119.20830932474
[M-H]-Not Available121.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000325
Predicted Molecular Properties
PropertyValueSource
Water Solubility14 g/LALOGPS
logP10(-1.3) g/LALOGPS
logP10(-1.7) g/LChemAxon
logS10(-1) g/LALOGPS
pKa (Strongest Acidic)8.68ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.1 m³·mol⁻¹ChemAxon
Polarizability12.34 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
DarkChem[M+H]+128.12731661259
DarkChem[M-H]-126.32631661259
AllCCS[M+H]+131.36532859911
AllCCS[M-H]-125.69132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-HydroxymethyluracilOCC1=CNC(=O)NC1=O2638.6Standard polar33892256
5-HydroxymethyluracilOCC1=CNC(=O)NC1=O1642.2Standard non polar33892256
5-HydroxymethyluracilOCC1=CNC(=O)NC1=O1927.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxymethyluracil,1TMS,isomer #1C[Si](C)(C)OCC1=C[NH]C(=O)[NH]C1=O1640.3Semi standard non polar33892256
5-Hydroxymethyluracil,1TMS,isomer #2C[Si](C)(C)N1C=C(CO)C(=O)[NH]C1=O1661.3Semi standard non polar33892256
5-Hydroxymethyluracil,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C=C(CO)C1=O1651.3Semi standard non polar33892256
5-Hydroxymethyluracil,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C(=O)[NH]C1=O1750.4Semi standard non polar33892256
5-Hydroxymethyluracil,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C(=O)[NH]C1=O1887.2Standard non polar33892256
5-Hydroxymethyluracil,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C(=O)[NH]C1=O2159.1Standard polar33892256
5-Hydroxymethyluracil,2TMS,isomer #2C[Si](C)(C)OCC1=C[NH]C(=O)N([Si](C)(C)C)C1=O1738.3Semi standard non polar33892256
5-Hydroxymethyluracil,2TMS,isomer #2C[Si](C)(C)OCC1=C[NH]C(=O)N([Si](C)(C)C)C1=O1845.3Standard non polar33892256
5-Hydroxymethyluracil,2TMS,isomer #2C[Si](C)(C)OCC1=C[NH]C(=O)N([Si](C)(C)C)C1=O2078.8Standard polar33892256
5-Hydroxymethyluracil,2TMS,isomer #3C[Si](C)(C)N1C=C(CO)C(=O)N([Si](C)(C)C)C1=O1731.0Semi standard non polar33892256
5-Hydroxymethyluracil,2TMS,isomer #3C[Si](C)(C)N1C=C(CO)C(=O)N([Si](C)(C)C)C1=O1928.9Standard non polar33892256
5-Hydroxymethyluracil,2TMS,isomer #3C[Si](C)(C)N1C=C(CO)C(=O)N([Si](C)(C)C)C1=O2172.2Standard polar33892256
5-Hydroxymethyluracil,3TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1897.0Semi standard non polar33892256
5-Hydroxymethyluracil,3TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1951.4Standard non polar33892256
5-Hydroxymethyluracil,3TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1975.5Standard polar33892256
5-Hydroxymethyluracil,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=C[NH]C(=O)[NH]C1=O1907.1Semi standard non polar33892256
5-Hydroxymethyluracil,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CO)C(=O)[NH]C1=O1957.6Semi standard non polar33892256
5-Hydroxymethyluracil,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C=C(CO)C1=O1901.0Semi standard non polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C(=O)[NH]C1=O2225.1Semi standard non polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C(=O)[NH]C1=O2311.4Standard non polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C(=O)[NH]C1=O2326.3Standard polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1=C[NH]C(=O)N([Si](C)(C)C(C)(C)C)C1=O2174.9Semi standard non polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1=C[NH]C(=O)N([Si](C)(C)C(C)(C)C)C1=O2271.9Standard non polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC1=C[NH]C(=O)N([Si](C)(C)C(C)(C)C)C1=O2239.1Standard polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CO)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2234.9Semi standard non polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CO)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2333.4Standard non polar33892256
5-Hydroxymethyluracil,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CO)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2276.6Standard polar33892256
5-Hydroxymethyluracil,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2453.9Semi standard non polar33892256
5-Hydroxymethyluracil,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2551.9Standard non polar33892256
5-Hydroxymethyluracil,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2297.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Hydroxymethyluracil GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0923000000-56a7dc66579bc2dd485b2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Hydroxymethyluracil GC-EI-TOF (Non-derivatized)splash10-0a4i-0923000000-56a7dc66579bc2dd485b2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (Non-derivatized) - 70eV, Positivesplash10-03kc-4900000000-1cac35d0ba0cca9e8da82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5910000000-e4ecb5b2c252b1dd98a62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxymethyluracil GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxymethyluracil Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-3900000000-5914a7f193ef00b468132012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxymethyluracil Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0f89-9000000000-baed63743f1c3f212a8c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxymethyluracil Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0pc0-9000000000-0ff7e6cec32d4f6a93ce2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxymethyluracil , negative-QTOFsplash10-0006-1900000000-c15a268f199a45782f942017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxymethyluracil 20V, Negative-QTOFsplash10-0006-9200000000-37d9ec4a1e994196876b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxymethyluracil 40V, Negative-QTOFsplash10-0006-9200000000-743c2de03cb5f65bb4582021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxymethyluracil 35V, Negative-QTOFsplash10-0006-1900000000-9692a096d1a7d0bb32c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Hydroxymethyluracil 10V, Negative-QTOFsplash10-0006-7900000000-ebcc62da3f6c16c368f92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 10V, Positive-QTOFsplash10-004l-0900000000-4db52d8921bc6b9e27d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 20V, Positive-QTOFsplash10-004i-6900000000-74ddd3dbfd8e6a457bee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 40V, Positive-QTOFsplash10-000t-9100000000-b418e2767863592cb8de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 10V, Negative-QTOFsplash10-0006-2900000000-5c173dfa10b778d98c522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 20V, Negative-QTOFsplash10-0006-9500000000-b46a4f1e0f9872c639de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 40V, Negative-QTOFsplash10-0006-9000000000-6613bb83bb842d70dfc02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 10V, Positive-QTOFsplash10-004i-0900000000-c9b85bee66bc9b6f7fa52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 20V, Positive-QTOFsplash10-004i-5900000000-fb2fe160d3fd7a32fbfc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 40V, Positive-QTOFsplash10-05fr-9000000000-0e50a0012c8e06917b1a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 10V, Negative-QTOFsplash10-006x-1900000000-972ab29c67e5ac9b71022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 20V, Negative-QTOFsplash10-00dl-8900000000-e306682075b170218ba82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxymethyluracil 40V, Negative-QTOFsplash10-0006-9000000000-e3c2901699c5071255a02021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.12 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0052 +/- 0.0026 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified88.0 +/- 8.0 uMAdult (>18 years old)Both
Solid tumors
details
BloodDetected and Quantified42.0 +/- 21.0 uMAdult (>18 years old)Both
Solid tumors
details
BloodDetected and Quantified15.0 +/- 2.0 uMAdult (>18 years old)Both
Solid tumors
details
BloodDetected and Quantified63.0 +/- 5.0 uMAdult (>18 years old)Both
Solid tumors
details
BloodDetected and Quantified33.0 +/- 4.0 uMAdult (>18 years old)Both
Solid tumors
details
UrineDetected and Quantified0.0062 +/- 0.0023 umol/mmol creatinineAdult (>18 years old)BothSmoking details
Associated Disorders and Diseases
Disease References
Thymidine treatment
  1. Leyva A, Schornagel JH, Kraal I, Wadman SK, Pinedo HM: Clinical and biochemical studies of high-dose thymidine treatment in patients with solid tumors. J Cancer Res Clin Oncol. 1984;107(3):211-6. [PubMed:6736109 ]
Smoking
  1. Chen HJ, Wu CF, Huang JL: Measurement of urinary excretion of 5-hydroxymethyluracil in human by GC/NICI/MS: correlation with cigarette smoking, urinary TBARS and etheno DNA adduct. Toxicol Lett. 2005 Mar 15;155(3):403-10. [PubMed:15649624 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022061
KNApSAcK IDNot Available
Chemspider ID70544
KEGG Compound IDC03088
BioCyc IDCPD-254
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5456
PubChem Compound78168
PDB IDNot Available
ChEBI ID16964
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000168
Good Scents IDNot Available
References
Synthesis ReferenceAbbott, Mitchel Theodore. The cell-free synthesis of 5-hydroxymethyluracil. (1963), 140 pp
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Faure H, Coudray C, Mousseau M, Ducros V, Douki T, Bianchini F, Cadet J, Favier A: 5-Hydroxymethyluracil excretion, plasma TBARS and plasma antioxidant vitamins in adriamycin-treated patients. Free Radic Biol Med. 1996;20(7):979-83. [PubMed:8743984 ]
  2. Baker D, Liu P, Burdzy A, Sowers LC: Characterization of the substrate specificity of a human 5-hydroxymethyluracil glycosylase activity. Chem Res Toxicol. 2002 Jan;15(1):33-9. [PubMed:11800595 ]
  3. Loft S, Poulsen HE: Estimation of oxidative DNA damage in man from urinary excretion of repair products. Acta Biochim Pol. 1998;45(1):133-44. [PubMed:9701506 ]
  4. Ito T, van Kuilenburg AB, Bootsma AH, Haasnoot AJ, van Cruchten A, Wada Y, van Gennip AH: Rapid screening of high-risk patients for disorders of purine and pyrimidine metabolism using HPLC-electrospray tandem mass spectrometry of liquid urine or urine-soaked filter paper strips. Clin Chem. 2000 Apr;46(4):445-52. [PubMed:10759467 ]
  5. Kow YW: Repair of deaminated bases in DNA. Free Radic Biol Med. 2002 Oct 1;33(7):886-93. [PubMed:12361800 ]
  6. Kawasaki F, Beraldi D, Hardisty RE, McInroy GR, van Delft P, Balasubramanian S: Genome-wide mapping of 5-hydroxymethyluracil in the eukaryote parasite Leishmania. Genome Biol. 2017 Jan 30;18(1):23. doi: 10.1186/s13059-017-1150-1. [PubMed:28137275 ]
  7. Janouskova M, Vanikova Z, Nici F, Bohacova S, Vitovska D, Sanderova H, Hocek M, Krasny L: 5-(Hydroxymethyl)uracil and -cytosine as potential epigenetic marks enhancing or inhibiting transcription with bacterial RNA polymerase. Chem Commun (Camb). 2017 Dec 12;53(99):13253-13255. doi: 10.1039/c7cc08053k. [PubMed:29184924 ]