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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-02 10:18:02 UTC
Update Date2019-07-25 18:12:28 UTC
HMDB IDHMDB0003331
Secondary Accession Numbers
  • HMDB03331
Metabolite Identification
Common Name1-Methyladenosine
Description1-Methyladenosine, also known as M1A, 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-Methyladenosine is a strong basic compound (based on its pKa). Precise m6A mapping by m6A-CLIP/IP (briefly m6A-CLIP) revealed that a majority of m6A locates in the last exon of mRNAs in multiple tissues/cultured cells of mouse and human, and the m6A enrichment around stop codons is a coincidence that many stop codons locate round the start of last exons where m6A is truly enriched. The methylation of adenosine is directed by a large m6A methyltransferase complex containing METTL3 as the SAM-binding sub-unit. Insulin-like growth factor-2 mRNA-binding proteins 1, 2, and 3 (IGF2BP1–3) are reported as a novel class of m6A readers.
Structure
Data?1563860745
Synonyms
ValueSource
m1aChEBI
N1-MethyladenosineHMDB
N(1)-MethyladenosineHMDB
Chemical FormulaC11H15N5O4
Average Molecular Weight281.2679
Monoisotopic Molecular Weight281.112403993
IUPAC Name(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-imino-1-methyl-6,9-dihydro-1H-purin-9-yl)oxolane-3,4-diol
Traditional Name1-methyladenosine
CAS Registry Number15763-06-1
SMILES
CN1C=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C1=N
InChI Identifier
InChI=1S/C11H15N5O4/c1-15-3-14-10-6(9(15)12)13-4-16(10)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11-12,17-19H,2H2,1H3/t5-,7-,8-,11-/m1/s1
InChI KeyGFYLSDSUCHVORB-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
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monosaccharide
  • N-substituted imidazole
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Primary alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.33 g/LALOGPS
logP-1.8ALOGPS
logP-2.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)2.98ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area127.19 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.1 m³·mol⁻¹ChemAxon
Polarizability27.56 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-0790000000-1516313b8da901f28bbaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0790000000-1516313b8da901f28bbaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0980000000-be208cfd62e67d98bf67Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0920000000-266456505e459aed90d9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9260000000-df75440994d3681767baSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-7351900000-778aa9d9e15b6acad19dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uf0-0990000000-d2a48b28d5d54fab5f15Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-1510e824c4b3bc404014Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-59193e9776c5cc704743Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0190000000-4ba89d6b5f6346f13785Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0910000000-75e5e157192c62256eddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udi-0900000000-f51a7adbe93284cc633fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0udi-0900000000-2bcab3f498a3a7f4963cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0udi-0900000000-7976b81cb29dc82fb60bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-3df081c89b3bc3d51542Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-06si-1900000000-a81173c3e117179fcf34Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-ada4e622e88814c85e19Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0900000000-943dbe2cb7ab7a16983cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0012-0690000000-7ded552a1e7600aa85a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000t-0590000000-baf52d13e2aba197228aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-6488105a96116c2e7d3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-9bbdc90acacfdb29c608Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0190000000-4ba89d6b5f6346f13785Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0910000000-75e5e157192c62256eddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-f51a7adbe93284cc633fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0940000000-7bf78ed8c7e7d0a7aaefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-111942c283b07a7fbe9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-4900000000-3e1b66adc79286880543Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001j-0690000000-014387065eec31451d4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-cd5b6cd7bfcdf3c8a1caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-0900000000-1caa586963ed5992f3e3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Breast Milk
  • Feces
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.10 +/- 0.03 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0609 +/- 0.0181 uMAdult (>18 years old)Both
Normal
details
Breast MilkDetected and Quantified0.34 +/- 0.07 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)Female
Normal
details
UrineDetected and Quantified5.96 (0.00-12.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.37 +/- 0.37 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified2.03 +/- 0.20 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified2.19 +/- 0.33 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified18.0 +/- 1.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.7 (0.9-3.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.078 +/- 0.031 uMAdult (>18 years old)Both
Leukemia
details
BloodDetected and Quantified0.0860 +/- 0.0095 uMAdult (>18 years old)FemaleOvarian cancer details
BloodDetected and Quantified0.370 +/- 0.050 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified0.105 +/- 0.036 uMAdult (>18 years old)BothStomach cancer details
BloodDetected and Quantified0.096 +/- 0.095 uMAdult (>18 years old)BothHepatocellular cancer details
BloodDetected and Quantified0.094 +/- 0.063 uMAdult (>18 years old)BothCholangioma cancer details
BloodDetected and Quantified0.134 +/- 0.111 uMAdult (>18 years old)BothColon cancer details
BloodDetected and Quantified0.150 +/- 0.010 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified0.220 +/- 0.430 uMAdult (>18 years old)Both
Kidney disease
details
BloodDetected and Quantified0.310 +/- 0.010 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified0.370 +/- 0.200 uMAdult (>18 years old)Both
Uremia
details
BloodDetected and Quantified0.145 uMAdult (>18 years old)Female
Cervical cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not Quantified Adult (>18 years old)Female
Ovarian cancer
details
UrineDetected and Quantified4.7 +/- 1.3 umol/mmol creatinineAdult (>18 years old)BothUremia details
Associated Disorders and Diseases
Disease References
Leukemia
  1. Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Ovarian cancer
  1. Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
  2. Woo HM, Kim KM, Choi MH, Jung BH, Lee J, Kong G, Nam SJ, Kim S, Bai SW, Chung BC: Mass spectrometry based metabolomic approaches in urinary biomarker study of women's cancers. Clin Chim Acta. 2009 Feb;400(1-2):63-9. doi: 10.1016/j.cca.2008.10.014. Epub 2008 Oct 30. [PubMed:19010317 ]
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. Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
  3. 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 ]
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 ]
Stomach cancer
  1. Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Hepatocellular carcinoma
  1. Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Cholangiocarcinoma
  1. Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Colorectal cancer
  1. Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. 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 ]
Cervical cancer
  1. Ishiwata S, Itoh K, Yamaguchi T, Ishida N, Mizugaki M: Comparison of serum and urinary levels of modified nucleoside, 1-methyladenosine, in cancer patients using a monoclonal antibody-based inhibition ELISA. Tohoku J Exp Med. 1995 May;176(1):61-8. [PubMed:7482520 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021791
KNApSAcK IDNot Available
Chemspider ID17216227
KEGG Compound IDC02494
BioCyc ID1-METHYLADENOSINE
BiGG IDNot Available
Wikipedia LinkN6-Methyladenosine
METLIN ID6888
PubChem Compound27476
PDB IDNot Available
ChEBI ID16020
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
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. Reynaud C, Bruno C, Boullanger P, Grange J, Barbesti S, Niveleau A: Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. Cancer Lett. 1992 Jan 31;61(3):255-62. [PubMed:1739950 ]
  3. Uziel M, Smith LH, Taylor SA: Modified nucleosides in urine: selective removal and analysis. Clin Chem. 1976 Sep;22(9):1451-5. [PubMed:954194 ]
  4. 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 ]
  5. 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 ]
  6. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  7. Takahashi R, Shiono T, Tamai M, Itoh K, Mizugaki M: [Expression of modified nucleoside, 1-methyladenosine in intraocular tumors and the retinas]. Nippon Ganka Gakkai Zasshi. 1993 Jan;97(1):43-9. [PubMed:8434538 ]