Record Information
Version2.0
Creation Date2012-08-09 09:25:09 -0600
Update Date2015-06-03 17:21:39 -0600
Secondary Accession Numbers
  • ECMDB21501
Identification
Name:5-Methyldeoxycytidine triphosphate
Description5-methyldeoxycytidine triphosphate is a member of the chemical class known as Pyrimidine 2'-deoxyribonucleoside Triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking an hydroxyl group at position 2. This is a methylated form of dCTP. Methylation of nucleotides and nucleosides can occur spontaneously through the action of alkylating reagents.
Structure
Thumb
Synonyms:
  • 2'-DEOXY-5-METHYLCYTIDINE 5'-(TETRAHYDROGEN TRIPHOSPHATE)
  • 2'-DEOXY-5-methylcytidine 5'-(tetrahydrogen triphosphoric acid)
  • 5-Methyl deoxycytidine-5'-triphosphate
  • 5-Methyl deoxycytidine-5'-triphosphoric acid
  • 5-Methyl deoxycytidine-triphosphate
  • 5-Methyl deoxycytidine-triphosphoric acid
  • 5-Methyl-2'-deoxycytidine 5'-triphosphate
  • 5-Methyl-2'-deoxycytidine 5'-triphosphoric acid
  • 5-Methyl-dCTP
  • 5-Methyldeoxycytidine triphosphate
  • 5-Methyldeoxycytidine triphosphoric acid
Chemical Formula:C10H18N3O13P3
Weight:Average: 481.1835
Monoisotopic: 481.005247213
InChI Key:NGYHUCPPLJOZIX-XLPZGREQSA-N
InChI:InChI=1S/C10H18N3O13P3/c1-5-3-13(10(15)12-9(5)11)8-2-6(14)7(24-8)4-23-28(19,20)26-29(21,22)25-27(16,17)18/h3,6-8,14H,2,4H2,1H3,(H,19,20)(H,21,22)(H2,11,12,15)(H2,16,17,18)/t6-,7+,8+/m0/s1
CAS number:22003-12-9
IUPAC Name:{[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(2-hydroxy-4-imino-5-methyl-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name:[hydroxy({hydroxy[(2R,3S,5R)-3-hydroxy-5-(2-hydroxy-4-imino-5-methylpyrimidin-1-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphoryl]oxyphosphonic acid
SMILES:[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=C(C)C(=N)N=C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside triphosphates. These are pyrimidine nucleotides with a triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine deoxyribonucleotides
Direct ParentPyrimidine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside triphosphate
  • Aminopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.07 g/LALOGPS
logP-0.8ALOGPS
logP-3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)2.27ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area248.96 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.42 m³·mol⁻¹ChemAxon
Polarizability37.01 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-3581080fe7023f8ef5c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2901000000-84e05e845336e7385f21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2900000000-92cc6984f0b35bff5fabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-0210900000-064fad5354f4cd7aa55bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-9740100000-28e13409cfe3a6afe6feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9610000000-23d21be03a2a7ceed4afView in MoNA
References
References:
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61766
HMDB IDNot Available
Pubchem Compound ID161376
Kegg IDNot Available
ChemSpider ID141756
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand Expo523

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Specific for pyrimidine substrates. Acts on 5-methyl- dCTP, CTP and dCTP in decreasing order
Gene Name:
nudG
Uniprot ID:
P77788
Molecular weight:
15046
Reactions
CTP + H(2)O = CMP + diphosphate.