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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:57:49 UTC
HMDB IDHMDB0001563
Secondary Accession Numbers
  • HMDB01563
Metabolite Identification
Common Name1-Methylguanosine
Description1-Methylguanosine, also known as M1G, 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. 1-Methylguanosine has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make 1-methylguanosine a potential biomarker for the consumption of these foods. 1-Methylguanosine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 1-Methylguanosine.
Structure
Data?1582752210
Synonyms
ValueSource
m1gChEBI
N1-MethylguanosineChEBI
N-MethylguanosineMeSH
1-Methyl-guanosineHMDB
MethylguanosineHMDB
TRMD ProteinHMDB
Chemical FormulaC11H15N5O5
Average Molecular Weight297.2673
Monoisotopic Molecular Weight297.107318615
IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one
Traditional Name1-methylguanosine
CAS Registry Number2140-65-0
SMILES
CN1C(N)=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=O
InChI Identifier
InChI=1S/C11H15N5O5/c1-15-9(20)5-8(14-11(15)12)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14)/t4-,6-,7-,10-/m1/s1
InChI KeyUTAIYTHAJQNQDW-KQYNXXCUSA-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
  • 6-oxopurine
  • Purinone
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Vinylogous amide
  • Lactam
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.1 g/LALOGPS
logP-1.8ALOGPS
logP-2.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)1.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area146.43 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.52 m³·mol⁻¹ChemAxon
Polarizability28.17 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalBaker166.92630932474
DeepCCS[M+H]+ExperimentalBaker168.80330932474
AllCCS[M-H]-ExperimentalNot Available166.926http://allccs.zhulab.cn/database/detail?ID=AllCCS00001914
AllCCS[M+H]+ExperimentalNot Available168.803http://allccs.zhulab.cn/database/detail?ID=AllCCS00001914
DarkChem[M+H]+PredictedNot Available166.16131661259
DarkChem[M-H]-PredictedNot Available164.20131661259
AllCCS[M+H]+PredictedNot Available165.7732859911
AllCCS[M-H]-PredictedNot Available166.57532859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
1-Methylguanosine,1TMS,#12799.2744https://arxiv.org/abs/1905.12712
1-Methylguanosine,1TMS,#22809.2324https://arxiv.org/abs/1905.12712
1-Methylguanosine,1TMS,#32807.8784https://arxiv.org/abs/1905.12712
1-Methylguanosine,1TMS,#42839.0806https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TMS,#12747.496https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TMS,#22737.872https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TMS,#32774.1162https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TMS,#42756.8665https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TMS,#52785.4175https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TMS,#62789.5073https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TMS,#72769.3267https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TMS,#12713.3096https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TMS,#22744.5142https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TMS,#32738.9875https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TMS,#42759.8508https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TMS,#52757.7993https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TMS,#62781.625https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TMS,#72773.3208https://arxiv.org/abs/1905.12712
1-Methylguanosine,1TBDMS,#13042.7427https://arxiv.org/abs/1905.12712
1-Methylguanosine,1TBDMS,#23044.7546https://arxiv.org/abs/1905.12712
1-Methylguanosine,1TBDMS,#33045.2126https://arxiv.org/abs/1905.12712
1-Methylguanosine,1TBDMS,#43074.4043https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TBDMS,#13193.8857https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TBDMS,#23197.5034https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TBDMS,#33235.9219https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TBDMS,#43191.4153https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TBDMS,#53241.6108https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TBDMS,#63236.2854https://arxiv.org/abs/1905.12712
1-Methylguanosine,2TBDMS,#73215.4692https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TBDMS,#13380.6665https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TBDMS,#23404.2805https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TBDMS,#33408.8555https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TBDMS,#43399.0984https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TBDMS,#53390.48https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TBDMS,#63418.72https://arxiv.org/abs/1905.12712
1-Methylguanosine,3TBDMS,#73412.7246https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0avr-9160000000-c71871a3455821cc0cd82017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000t-6902400000-f62364e1c258d1b219102017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-83049daf172a0028ef3b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-297efbbdd4c56947d85a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-06sj-0900000000-c3b78851ce459f2b05332021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03di-0900000000-ac1e4f86f920ef0213ec2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-dbbf8ee001ac7ebe86952021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-0910000000-74105b75d5b6ac0196862021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014j-0900000000-1a00daf15f672985739a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udj-0960000000-d5cca20daa4759338cf82021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-76bb8e0e68de58eab7cb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-5900000000-e057b071aa699b98597c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014j-0961000000-b3371b576dbf1f20bc3b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-0900000000-e12157cd4c291c524eca2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-014j-0951000000-066a7ef362ef491180352021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-ac243405a8007cad38502021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-206489ed223c9cc326132021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-1900000000-46402612942543fd8d3b2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0940000000-cdf8a532f9a4c0deef482016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-e8970970eb1ddb9b37bd2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-0900000000-f7ea94f03c9a16bf02d42016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ot-0490000000-97864ef8e1af3fce3c342016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0910000000-d1f62b75fc81d9c17e962016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1900000000-6dceb96152f42447d0bb2016-08-03View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Breast Milk
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0461 +/- 0.0569 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.046 +/- 0.019 uMAdult (>18 years old)BothNormal details
Breast MilkDetected and Quantified0.68+/- 0.18 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.86 +/- 0.22 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified2.4 +/- 0.7 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.099 +/- 0.021 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified0.140 +/- 0.0801 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified0.078 +/- 0.010 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified0.140 +/- 0.020 uMAdult (>18 years old)BothUremia details
BloodDetected and Quantified0.120 +/- 0.020 uMAdult (>18 years old)Both
Uremia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified0.97 +/- 0.33 umol/mmol creatinineAdult (>18 years old)Not SpecifiedBreast cancer details
UrineDetected and Quantified9.5 +/- 0.8 umol/mmol creatinineAdult (>18 years old)BothUremia 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. 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 ]
  2. 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 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Perillyl alcohol administration for cancer treatment
  1. Zheng YF, Kong HW, Xiong JH, Lv S, Xu GW: Clinical significance and prognostic value of urinary nucleosides in breast cancer patients. Clin Biochem. 2005 Jan;38(1):24-30. [PubMed:15607313 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022690
KNApSAcK IDNot Available
Chemspider ID86996
KEGG Compound IDC04545
BioCyc IDCPD0-1043
BiGG IDNot Available
Wikipedia Link7-Methylguanosine
METLIN ID6324
PubChem Compound96373
PDB IDNot Available
ChEBI ID19062
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000337
References
Synthesis ReferenceErmolinsky Boris S; Efimtseva Ekaterina V; Alexeev Cyrill S; Mikhailov Sergey N; Balzarini Jan; De Clercq Erik Dinucleoside monophosphates containing AZT and 1-methyladenosine or 7-methylguanosine. Nucleosides, nucleotides & nucleic acids (2003), 22(5-8), 853-5.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Heldman DA, Grever MR, Miser JS, Trewyn RW: Relationship of urinary excretion of modified nucleosides to disease status in childhood acute lymphoblastic leukemia. J Natl Cancer Inst. 1983 Aug;71(2):269-73. [PubMed:6576186 ]
  2. Szabo LD, Keresztes P, Pallos JP, Csato E, Predmerszky T: Study of nucleic acid metabolism in two astronauts. Adv Space Res. 1984;4(10):15-8. [PubMed:11539621 ]
  3. Liebich HM, Di Stefano C, Wixforth A, Schmid HR: Quantitation of urinary nucleosides by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):193-7. [PubMed:9129323 ]