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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 14:16:08 UTC
Update Date2020-10-09 21:03:42 UTC
HMDB IDHMDB0004824
Secondary Accession Numbers
  • HMDB04824
Metabolite Identification
Common NameN2,N2-Dimethylguanosine
DescriptionN2,N2-Dimethylguanosine, also known as M22G or m(2)(2)g, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. The mean levels of urinary N2,N2-Dimethylguanosine in the patients with colorectal cancer are significantly higher than those in patients with intestinal villous adenoma or the healthy adults (PMID 15991285 ). N2,N2-Dimethylguanosine is a moderately basic compound (based on its pKa).
Structure
Data?1582752315
Synonyms
ValueSource
2,2-DimethylguanosineChEBI
2-(Dimethylamino)-9-(beta-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-oneChEBI
2-Dimethylamino-6-oxypurine ribosideChEBI
m22gChEBI
N2-DimethylguanosineChEBI
2-(Dimethylamino)-9-(b-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-oneGenerator
2-(Dimethylamino)-9-(β-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-oneGenerator
m(2)2gHMDB
m2(2)gHMDB
m(2)(2)gHMDB
N,N- DimethylguanosineHMDB
N,N-Dimethyl-guanosineHMDB
N(2),N(2)-DimethylguanosineHMDB
N2,N2-DimethylguanosineMeSH
Chemical FormulaC12H17N5O5
Average Molecular Weight311.2939
Monoisotopic Molecular Weight311.122968679
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-6,9-dihydro-3H-purin-6-one
Traditional Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-3H-purin-6-one
CAS Registry Number2140-67-2
SMILES
CN(C)C1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C12H17N5O5/c1-16(2)12-14-9-6(10(21)15-12)13-4-17(9)11-8(20)7(19)5(3-18)22-11/h4-5,7-8,11,18-20H,3H2,1-2H3,(H,14,15,21)/t5-,7-,8-,11-/m1/s1
InChI KeyRSPURTUNRHNVGF-IOSLPCCCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Hypoxanthine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Dialkylarylamine
  • Aminopyrimidine
  • Hydroxypyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point235 - 236 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility13.7 g/LALOGPS
logP-1.2ALOGPS
logP-1.6ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.85ChemAxon
pKa (Strongest Basic)2.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.44 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.26 m³·mol⁻¹ChemAxon
Polarizability30.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ac3-9180000000-6b74485ca69b8a0937c1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01c0-3391310000-26de80f9bc78e87a644aSpectrum
LC-MS/MSLC-MS/MS Spectrum - CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 10V, Positivesplash10-001i-0900000000-6033a973f510df066a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0913000000-0a30a8ffbe4d72e234cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-8d944e0314b44af1f027Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-1900000000-ec4fb5d37def9d84c5a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-0759000000-2b4a326aad3ce87ea5e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0910000000-10561e691bbf8dac63d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1900000000-c3a8e7eb56de154adbdbSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.031 +/- 0.004 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.029 +/- 0.09 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0289 +/- 0.0151 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.360 (0.224-0.496) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.44 +/- 0.09 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified0.760 +/- 0.288 uMAdult (>18 years old)Both
Uremia
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Kidney disease
  1. Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6. [PubMed:9607216 ]
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023432
KNApSAcK IDNot Available
Chemspider ID83878
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID7086
PubChem Compound92919
PDB IDNot Available
ChEBI ID19289
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000454
References
Synthesis ReferenceGerster, John F.; Robins, Roland K. Purine nucleosides. X. The synthesis of certain naturally occurring 2-substituted amino-9-b-D-ribofuranosylpurin-6(1 H)-ones (N2-substituted guanosines). Journal of the American Chemical Society (1965), 87(16), 3752-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. [PubMed:15116424 ]
  2. Zheng YF, Yang J, Zhao XJ, Feng B, Kong HW, Chen YJ, Lv S, Zheng MH, Xu GW: Urinary nucleosides as biological markers for patients with colorectal cancer. World J Gastroenterol. 2005 Jul 7;11(25):3871-6. [PubMed:15991285 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]