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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:17 UTC
Update Date2023-02-21 17:16:29 UTC
HMDB IDHMDB0002894
Secondary Accession Numbers
  • HMDB02894
Metabolite Identification
Common Name5-Methylcytosine
Description5-Methylcytosine is a methylated nucleotide base found in eukaryotic DNA. In animals, the DNA methylation of cytosine to form 5-methylcytosine is found primarily in the palindromic sequence CpG. In plants, the methylated sequence is CpNpGp, where N can be any base. -- Pubchem; 5-Methylcytosine is a methylated form of cytosine in which a methyl group is attached to carbon 5, altering its structure without altering its base-pairing properties. -- Wikipedia ; 5-Methylcytosine is an epigenetic modification formed by the action of DNA methyltransferases. In bacteria, 5-methylcytosine can be found at a variety of sites, and is often used as a marker to protect DNA from being cut by native methylation-sensitive restriction enzymes. In plants, 5-methylcytosine occurs at both CpG and CpNpG sequences. In fungi and animals, 5-methylcytosine predominately occurs at CpG dinucleotides. Although most eukaryotes methylate only a small percentage of these sites, in vertebrates 70-80% of CpG cytosines are methylated. -- Wikipedia .
Structure
Data?1676999789
Synonyms
ValueSource
4-Amino-5-methyl-2(1H)-pyrimidinoneChEBI
4-Amino-5-methyl-2-pyrimidinolChEBI
4-Amino-5-methyl-2-(1H)-pyrimidinoneHMDB
5-Methyl-cytosineHMDB
5-Methylcytosine>96HMDB
Monohydrochloride, 5-methylcytosineHMDB
5 MethylcytosineHMDB
5 Methylcytosine monohydrochlorideHMDB
5-Methylcytosine monohydrochlorideHMDB
Chemical FormulaC5H7N3O
Average Molecular Weight125.1286
Monoisotopic Molecular Weight125.058911861
IUPAC Name6-amino-5-methyl-1,2-dihydropyrimidin-2-one
Traditional Name5-methylcytosine
CAS Registry Number554-01-8
SMILES
CC1=C(N)NC(=O)N=C1
InChI Identifier
InChI=1S/C5H7N3O/c1-3-2-7-5(9)8-4(3)6/h2H,1H3,(H3,6,7,8,9)
InChI KeyLRSASMSXMSNRBT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxypyrimidines. These are organic compounds containing a hydroxyl group attached 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 ParentHydroxypyrimidines
Alternative Parents
Substituents
  • Hydroxypyrimidine
  • Imidolactam
  • Hydropyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point270 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility34.5 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.91 g/LALOGPS
logP-0.63ALOGPS
logP-0.75ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.08ChemAxon
pKa (Strongest Basic)3.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.48 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.37 m³·mol⁻¹ChemAxon
Polarizability11.89 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]+125.07331661259
DarkChem[M-H]-121.6431661259
DeepCCS[M+H]+130.04530932474
DeepCCS[M-H]-126.31330932474
DeepCCS[M-2H]-163.7530932474
DeepCCS[M+Na]+139.19330932474
AllCCS[M+H]+126.832859911
AllCCS[M+H-H2O]+122.032859911
AllCCS[M+NH4]+131.232859911
AllCCS[M+Na]+132.532859911
AllCCS[M-H]-122.832859911
AllCCS[M+Na-2H]-125.032859911
AllCCS[M+HCOO]-127.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-MethylcytosineCC1=C(N)NC(=O)N=C12505.6Standard polar33892256
5-MethylcytosineCC1=C(N)NC(=O)N=C11502.8Standard non polar33892256
5-MethylcytosineCC1=C(N)NC(=O)N=C11675.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Methylcytosine,1TMS,isomer #1CC1=C(N[Si](C)(C)C)[NH]C(=O)N=C11595.7Semi standard non polar33892256
5-Methylcytosine,1TMS,isomer #1CC1=C(N[Si](C)(C)C)[NH]C(=O)N=C11622.0Standard non polar33892256
5-Methylcytosine,1TMS,isomer #1CC1=C(N[Si](C)(C)C)[NH]C(=O)N=C12246.3Standard polar33892256
5-Methylcytosine,1TMS,isomer #2CC1=C(N)N([Si](C)(C)C)C(=O)N=C11555.7Semi standard non polar33892256
5-Methylcytosine,1TMS,isomer #2CC1=C(N)N([Si](C)(C)C)C(=O)N=C11598.6Standard non polar33892256
5-Methylcytosine,1TMS,isomer #2CC1=C(N)N([Si](C)(C)C)C(=O)N=C12274.5Standard polar33892256
5-Methylcytosine,2TMS,isomer #1CC1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N=C11688.3Semi standard non polar33892256
5-Methylcytosine,2TMS,isomer #1CC1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N=C11727.5Standard non polar33892256
5-Methylcytosine,2TMS,isomer #1CC1=C(N[Si](C)(C)C)N([Si](C)(C)C)C(=O)N=C12014.7Standard polar33892256
5-Methylcytosine,2TMS,isomer #2CC1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N=C11540.5Semi standard non polar33892256
5-Methylcytosine,2TMS,isomer #2CC1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N=C11671.8Standard non polar33892256
5-Methylcytosine,2TMS,isomer #2CC1=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C(=O)N=C12058.4Standard polar33892256
5-Methylcytosine,3TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N=C11756.7Semi standard non polar33892256
5-Methylcytosine,3TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N=C11789.4Standard non polar33892256
5-Methylcytosine,3TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C(=O)N=C11829.2Standard polar33892256
5-Methylcytosine,1TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N=C11830.8Semi standard non polar33892256
5-Methylcytosine,1TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N=C11825.9Standard non polar33892256
5-Methylcytosine,1TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)[NH]C(=O)N=C12366.8Standard polar33892256
5-Methylcytosine,1TBDMS,isomer #2CC1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N=C11795.4Semi standard non polar33892256
5-Methylcytosine,1TBDMS,isomer #2CC1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N=C11803.8Standard non polar33892256
5-Methylcytosine,1TBDMS,isomer #2CC1=C(N)N([Si](C)(C)C(C)(C)C)C(=O)N=C12348.2Standard polar33892256
5-Methylcytosine,2TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N=C12099.8Semi standard non polar33892256
5-Methylcytosine,2TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N=C12109.4Standard non polar33892256
5-Methylcytosine,2TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N=C12170.1Standard polar33892256
5-Methylcytosine,2TBDMS,isomer #2CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N=C11991.8Semi standard non polar33892256
5-Methylcytosine,2TBDMS,isomer #2CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N=C12091.4Standard non polar33892256
5-Methylcytosine,2TBDMS,isomer #2CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C(=O)N=C12188.5Standard polar33892256
5-Methylcytosine,3TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N=C12336.9Semi standard non polar33892256
5-Methylcytosine,3TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N=C12397.1Standard non polar33892256
5-Methylcytosine,3TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C(=O)N=C12164.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-MS (1 TMS)splash10-001i-4900000000-73c143c463607343e59d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-MS (2 TMS)splash10-0udi-3950000000-332af504e32034e6ea672014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-MS (3 TMS)splash10-0059-3934000000-6eb3288b70641721809a2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-EI-TOF (Non-derivatized)splash10-0udi-2970000000-9bae58e66a60384a4b472017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-EI-TOF (Non-derivatized)splash10-0udi-1890000000-547f8dd8c93c7e653e8c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-EI-TOF (Non-derivatized)splash10-0udi-1960000000-eb731b2f4381755effcf2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-EI-TOF (Non-derivatized)splash10-0fk9-8970000000-8e71ebdb5a55e24263442017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-MS (Non-derivatized)splash10-001i-4900000000-73c143c463607343e59d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-MS (Non-derivatized)splash10-0udi-3950000000-332af504e32034e6ea672017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Methylcytosine GC-MS (Non-derivatized)splash10-0059-3934000000-6eb3288b70641721809a2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methylcytosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-6900000000-cb2ceeb7f5bd935faa192017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methylcytosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methylcytosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine , negative-QTOFsplash10-0089-9600000000-aa86d3c38a48514c2a4d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine LC-ESI-QQ , positive-QTOFsplash10-004i-0900000000-045ecf28f36874a7b1462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine LC-ESI-QQ , positive-QTOFsplash10-004i-0900000000-17d0aa6deb42e49740692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine LC-ESI-QQ , positive-QTOFsplash10-0a59-6900000000-2ba4efb5ece00114fe132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine LC-ESI-QQ , positive-QTOFsplash10-0a59-9300000000-1a71fa46d7b0fd6269f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine LC-ESI-QQ , positive-QTOFsplash10-0zgi-9000000000-61088abf446eafee8dd22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine LC-ESI-QTOF , positive-QTOFsplash10-004i-0900000000-a1c6199ce762a7fb68552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine LC-ESI-QTOF , positive-QTOFsplash10-004i-1900000000-e85c44ed5cd560d17d602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine , positive-QTOFsplash10-004i-0900000000-7ce4adb73357e05cc8b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 10V, Positive-QTOFsplash10-004i-3900000000-b2832b699d97e3d2bfaa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 10V, Negative-QTOFsplash10-008c-9300000000-7427dfe87925963304112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 35V, Positive-QTOFsplash10-004i-0900000000-bb76593a12a5655ad7562021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 20V, Negative-QTOFsplash10-0006-9000000000-011e24f4e333703cb5cb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 35V, Positive-QTOFsplash10-004i-0900000000-a84f7e26153cb2255dc52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 35V, Positive-QTOFsplash10-004i-0900000000-7e7dde0bdedd7250d6172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 10V, Positive-QTOFsplash10-004i-0900000000-bb789d0a4d3bce440b9a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 30V, Positive-QTOFsplash10-004i-1900000000-e85c44ed5cd560d17d602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 40V, Negative-QTOFsplash10-0006-9000000000-efc3476af90e31d453f82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methylcytosine 20V, Positive-QTOFsplash10-0a7i-5900000000-e991fa239913a7dfb67d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methylcytosine 10V, Positive-QTOFsplash10-004i-0900000000-63ea0e71e72b5a60804b2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methylcytosine 20V, Positive-QTOFsplash10-004i-5900000000-8b8c84afdb6f620a47062015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methylcytosine 40V, Positive-QTOFsplash10-0pb9-9300000000-a069a5c69d4eb3143d952015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methylcytosine 10V, Negative-QTOFsplash10-00di-1900000000-04225473bccf83af00d82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methylcytosine 20V, Negative-QTOFsplash10-00e9-9500000000-e5c525a63af7fcf813902015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methylcytosine 40V, Negative-QTOFsplash10-0006-9000000000-8eb88ca79a619c9357ae2015-09-15Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB004432
KNApSAcK IDNot Available
Chemspider ID58551
KEGG Compound IDC02376
BioCyc IDCPD0-2018
BiGG IDNot Available
Wikipedia Link5-Methylcytosine
METLIN ID3247
PubChem Compound65040
PDB IDNot Available
ChEBI ID27551
Food Biomarker OntologyNot Available
VMH ID5MTC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceUmetani, Hideki. Method for preparing 5-methylcytosine. Jpn. Kokai Tokkyo Koho (2006), 8 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pfeifer GP, You YH, Besaratinia A: Mutations induced by ultraviolet light. Mutat Res. 2005 Apr 1;571(1-2):19-31. Epub 2005 Jan 20. [PubMed:15748635 ]

Enzymes

General function:
Involved in DNA binding
Specific function:
Required for genome-wide de novo methylation and is essential for the establishment of DNA methylation patterns during development. DNA methylation is coordinated with methylation of histones. It modifies DNA in a non-processive manner and also methylates non-CpG sites. May preferentially methylate DNA linker between 2 nucleosomal cores and is inhibited by histone H1. Plays a role in paternal and maternal imprinting. Required for methylation of most imprinted loci in germ cells. Acts as a transcriptional corepressor for ZNF238. Can actively repress transcription through the recruitment of HDAC activity (By similarity).
Gene Name:
DNMT3A
Uniprot ID:
Q9Y6K1
Molecular weight:
101857.595
General function:
Involved in DNA binding
Specific function:
Required for genome-wide de novo methylation and is essential for the establishment of DNA methylation patterns during development. DNA methylation is coordinated with methylation of histones. May preferentially methylates nucleosomal DNA within the nucleosome core region. May function as transcriptional co-repressor by associating with CBX4 and independently of DNA methylation. Seems to be involved in gene silencing (By similarity). In association with DNMT1 and via the recruitment of CTCFL/BORIS, involved in activation of BAG1 gene expression by modulating dimethylation of promoter histone H3 at H3K4 and H3K9. Isoforms 4 and 5 are probably not functional due to the deletion of two conserved methyltransferase motifs. Function as transcriptional corepressor by associating with ZHX1.
Gene Name:
DNMT3B
Uniprot ID:
Q9UBC3
Molecular weight:
81309.795
General function:
Involved in DNA binding
Specific function:
Specifically methylates cytosine 38 in the anticodon loop of tRNA(Asp).
Gene Name:
TRDMT1
Uniprot ID:
O14717
Molecular weight:
44596.17
General function:
Involved in tRNA (cytosine-5-)-methyltransferase activity
Specific function:
RNA methyltransferase that methylates tRNAs, and possibly RNA polymerase III transcripts. Methylates cytosine to 5-methylcytosine (m5C) at position 34 of intron-containing tRNA(Leu)(CAA) precursors. Not able to modify tRNAs at positions 48 or 49. May act downstream of Myc to regulate epidermal cell growth and proliferation. Required for proper spindle assembly and chromosome segregation, independently of its methyltransferase activity.
Gene Name:
NSUN2
Uniprot ID:
Q08J23
Molecular weight:
82392.405
General function:
Involved in DNA binding
Specific function:
S-adenosyl-L-methionine + DNA = S-adenosyl-L- homocysteine + DNA containing 5-methylcytosine
Gene Name:
Not Available
Uniprot ID:
Q59FP7
Molecular weight:
182018.2