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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 07:58:51 UTC
Update Date2021-09-14 15:46:22 UTC
HMDB IDHMDB0003950
Secondary Accession Numbers
  • HMDB03950
Metabolite Identification
Common Name7-Methylinosine
Description7-Methylinosine is an endogenous methylated nucleoside found in human fluids; methylated purine bases are present in higher amounts in tumor-bearing patients compared to healthy controls.DNA hypermethylation is a common finding in malignant cells and has been explored as a therapeutic target for hypomethylating agents. When a chemical bonds to DNA, the DNA becomes damaged, and proper and complete replication cannot occur to make the normal intended cell. A DNA adduct is an abnormal piece of DNA covalently-bonded to a cancer-causing chemical. This has shown to be the start of a cancerous cell, or carcinogenesis. DNA adducts in scientific experiments are used as bio-markers and as such are themselves measured to reflect quantitatively, for comparison, the amount of cancer in the subject. 7-Methylguanosine has been identified in human urine and serum. (PMID: 3506820 , 17044778 , 17264127 , 16799933 , 15906010 ).
Structure
Data?1582752293
Synonyms
ValueSource
(e)-S-2-OctenoateHMDB
(e)-S-2-Octenoate CoAHMDB
(e)-S-2-Octenoate coenzyme AHMDB
(e)-S-2-Octenoic acidHMDB
2,3-trans-Octenoyl coenzyme AHMDB
Oct-2-trans-enoyl-CoAHMDB
Oct-2-trans-enoyl-coenzyme AHMDB
Oct-trans-2-enoyl coenzyme AHMDB
S-(2E)-2-OctenoateHMDB
S-(2E)-2-Octenoate CoAHMDB
S-(2E)-2-Octenoate coenzyme AHMDB
S-(2E)-2-Octenoic acidHMDB
trans-D2,3-Octenoyl-CoAHMDB
trans-D2,3-Octenoyl-coenzyme AHMDB
trans-Oct-2-enoyl-CoAHMDB
trans-Oct-2-enoyl-coenzyme AHMDB
7-MethylinosineMeSH
Chemical FormulaC11H15N4O5
Average Molecular Weight283.2606
Monoisotopic Molecular Weight283.10424461
IUPAC Name9-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-6,7-dihydro-3H-9λ⁵-purin-9-ylium
Traditional Name9-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-3H-9λ⁵-purin-9-ylium
CAS Registry Number20245-33-4
SMILES
CN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN2
InChI Identifier
InChI=1S/C11H14N4O5/c1-14-4-15(9-6(14)10(19)13-3-12-9)11-8(18)7(17)5(2-16)20-11/h3-5,7-8,11,16-18H,2H2,1H3/p+1/t5-,7-,8-,11?/m1/s1
InChI KeyVJNXUFOTKNTNPG-YNJARDAQSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentMedium-chain 2-enoyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
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 Solubility4.59 g/LALOGPS
logP-1.4ALOGPS
logP-6ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.12ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.19 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.09 m³·mol⁻¹ChemAxon
Polarizability27.06 ųChemAxon
Number of Rings3ChemAxon
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]+159.75630932474
DeepCCS[M-H]-157.36130932474
DeepCCS[M-2H]-191.3430932474
DeepCCS[M+Na]+166.09330932474
AllCCS[M+H]+162.732859911
AllCCS[M+H-H2O]+159.232859911
AllCCS[M+NH4]+165.932859911
AllCCS[M+Na]+166.932859911
AllCCS[M-H]-164.232859911
AllCCS[M+Na-2H]-163.532859911
AllCCS[M+HCOO]-162.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-MethylinosineCN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN23362.1Standard polar33892256
7-MethylinosineCN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN21539.5Standard non polar33892256
7-MethylinosineCN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN22946.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-Methylinosine,1TMS,isomer #1CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)C2=C1C(=O)N=C[NH]22679.6Semi standard non polar33892256
7-Methylinosine,1TMS,isomer #2CN1C=[N+](C2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C2=C1C(=O)N=C[NH]22690.6Semi standard non polar33892256
7-Methylinosine,1TMS,isomer #3CN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=C[NH]22688.1Semi standard non polar33892256
7-Methylinosine,1TMS,isomer #4CN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN2[Si](C)(C)C2763.8Semi standard non polar33892256
7-Methylinosine,2TMS,isomer #1CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C2=C1C(=O)N=C[NH]22619.6Semi standard non polar33892256
7-Methylinosine,2TMS,isomer #2CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=C[NH]22627.6Semi standard non polar33892256
7-Methylinosine,2TMS,isomer #3CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN2[Si](C)(C)C2707.4Semi standard non polar33892256
7-Methylinosine,2TMS,isomer #4CN1C=[N+](C2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=C[NH]22642.4Semi standard non polar33892256
7-Methylinosine,2TMS,isomer #5CN1C=[N+](C2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)C2=C1C(=O)N=CN2[Si](C)(C)C2735.7Semi standard non polar33892256
7-Methylinosine,2TMS,isomer #6CN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C2730.0Semi standard non polar33892256
7-Methylinosine,3TMS,isomer #1CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=C[NH]22592.5Semi standard non polar33892256
7-Methylinosine,3TMS,isomer #2CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)C2=C1C(=O)N=CN2[Si](C)(C)C2675.1Semi standard non polar33892256
7-Methylinosine,3TMS,isomer #3CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C2675.4Semi standard non polar33892256
7-Methylinosine,3TMS,isomer #4CN1C=[N+](C2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C2700.0Semi standard non polar33892256
7-Methylinosine,4TMS,isomer #1CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C2675.8Semi standard non polar33892256
7-Methylinosine,4TMS,isomer #1CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C2925.2Standard non polar33892256
7-Methylinosine,4TMS,isomer #1CN1C=[N+](C2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C3003.9Standard polar33892256
7-Methylinosine,1TBDMS,isomer #1CN1C=[N+](C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C2=C1C(=O)N=C[NH]22915.8Semi standard non polar33892256
7-Methylinosine,1TBDMS,isomer #2CN1C=[N+](C2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C2=C1C(=O)N=C[NH]22924.6Semi standard non polar33892256
7-Methylinosine,1TBDMS,isomer #3CN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C[NH]22925.5Semi standard non polar33892256
7-Methylinosine,1TBDMS,isomer #4CN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3018.1Semi standard non polar33892256
7-Methylinosine,2TBDMS,isomer #1CN1C=[N+](C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C2=C1C(=O)N=C[NH]23047.6Semi standard non polar33892256
7-Methylinosine,2TBDMS,isomer #2CN1C=[N+](C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C[NH]23051.1Semi standard non polar33892256
7-Methylinosine,2TBDMS,isomer #3CN1C=[N+](C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3181.3Semi standard non polar33892256
7-Methylinosine,2TBDMS,isomer #4CN1C=[N+](C2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C2=C1C(=O)N=C[NH]23057.1Semi standard non polar33892256
7-Methylinosine,2TBDMS,isomer #5CN1C=[N+](C2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3190.3Semi standard non polar33892256
7-Methylinosine,2TBDMS,isomer #6CN1C=[N+](C2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3187.9Semi standard non polar33892256
7-Methylinosine,3TBDMS,isomer #1CN1C=[N+](C2O[C@H](CO[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)C2=C1C(=O)N=C[NH]23216.2Semi standard non polar33892256
7-Methylinosine,3TBDMS,isomer #2CN1C=[N+](C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3342.9Semi standard non polar33892256
7-Methylinosine,3TBDMS,isomer #3CN1C=[N+](C2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3348.8Semi standard non polar33892256
7-Methylinosine,3TBDMS,isomer #4CN1C=[N+](C2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3351.8Semi standard non polar33892256
7-Methylinosine,4TBDMS,isomer #1CN1C=[N+](C2O[C@H](CO[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)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3485.1Semi standard non polar33892256
7-Methylinosine,4TBDMS,isomer #1CN1C=[N+](C2O[C@H](CO[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)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3680.9Standard non polar33892256
7-Methylinosine,4TBDMS,isomer #1CN1C=[N+](C2O[C@H](CO[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)C2=C1C(=O)N=CN2[Si](C)(C)C(C)(C)C3342.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-Methylinosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pi3-9260000000-73a089c04b3583333ac22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Methylinosine GC-MS (3 TMS) - 70eV, Positivesplash10-052r-9320600000-241c370634af6809981e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Methylinosine 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 - 7-Methylinosine 10V, Positive-QTOFsplash10-0udi-0910000000-146dbb54a52a8785854c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methylinosine 20V, Positive-QTOFsplash10-0udi-0900000000-0c27621ece50175a2d002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methylinosine 40V, Positive-QTOFsplash10-00di-1900000000-d6d90662053a4eec92252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methylinosine 10V, Positive-QTOFsplash10-0udi-0910000000-aa2b791d7191373f0ab32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methylinosine 20V, Positive-QTOFsplash10-0udi-0900000000-3222ffb615f3fdc62e502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methylinosine 40V, Positive-QTOFsplash10-0uk9-1900000000-29f7e30c0ce3a084c5f12021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023268
KNApSAcK IDNot Available
Chemspider ID4444335
KEGG Compound IDC05276
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280769
PDB IDNot Available
ChEBI ID27537
Food Biomarker OntologyNot Available
VMH IDHC01415
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
  2. Kammerer B, Frickenschmidt A, Muller CE, Laufer S, Gleiter CH, Liebich H: Mass spectrometric identification of modified urinary nucleosides used as potential biomedical markers by LC-ITMS coupling. Anal Bioanal Chem. 2005 Jun;382(4):1017-26. Epub 2005 May 19. [PubMed:15906010 ]
  3. Cho SH, Jung BH, Lee SH, Lee WY, Kong G, Chung BC: Direct determination of nucleosides in the urine of patients with breast cancer using column-switching liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2006 Nov;20(11):1229-36. [PubMed:16799933 ]
  4. Yang TH, Hu ML: Intracellular levels of S-adenosylhomocysteine but not homocysteine are highly correlated to the expression of nm23-H1 and the level of 5-methyldeoxycytidine in human hepatoma cells with different invasion activities. Nutr Cancer. 2006;55(2):224-31. [PubMed:17044778 ]
  5. Liu Z, Liu S, Xie Z, Blum W, Perrotti D, Paschka P, Klisovic R, Byrd J, Chan KK, Marcucci G: Characterization of in vitro and in vivo hypomethylating effects of decitabine in acute myeloid leukemia by a rapid, specific and sensitive LC-MS/MS method. Nucleic Acids Res. 2007;35(5):e31. Epub 2007 Jan 30. [PubMed:17264127 ]