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Record Information
Version3.6
Creation Date2006-08-02 10:18:02 UTC
Update Date2016-02-11 01:06:09 UTC
HMDB IDHMDB03331
Secondary Accession NumbersNone
Metabolite Identification
Common Name1-Methyladenosine
Description1-methyladenosine is one of the modified nucleosides, the levels of which are elevated in urine of patients with malignant tumors. Examination of expression of 1-methyladenosine is expected to be useful for the histological diagnosis of intraocular tumors. (PMID 8434538 ).
Structure
Thumb
Synonyms
ValueSource
m1aChEBI
N1-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 KeyInChIKey=GFYLSDSUCHVORB-IOSLPCCCSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine nucleosides. These 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 ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area127.19 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.1 m3·mol-1ChemAxon
Polarizability27.56 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a4i-0790000000-1516313b8da901f28bbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uf0-0990000000-d2a48b28d5d54fab5f15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-1510e824c4b3bc404014View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-59193e9776c5cc704743View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0190000000-4ba89d6b5f6346f13785View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-0910000000-75e5e157192c62256eddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udi-0900000000-f51a7adbe93284cc633fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0udi-0900000000-2bcab3f498a3a7f4963cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0udi-0900000000-7976b81cb29dc82fb60bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-3df081c89b3bc3d51542View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-06si-1900000000-a81173c3e117179fcf34View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.10 +/- 0.03 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
BiofluidStatusValueAgeSexConditionReferenceDetails
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 Quantified0.145 uMAdult (>18 years old)Female
Cervical cancer
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
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. [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. [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. [7482520 ]
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. [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. [7482520 ]
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. [9607216 ]
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. [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. [7482520 ]
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. [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. [7482520 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021791
KNApSAcK IDNot Available
Chemspider ID17216227
KEGG Compound IDC02494
BioCyc ID1-METHYLADENOSINE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03331
Metagene LinkHMDB03331
METLIN ID6888
PubChem Compound27476
PDB IDNot Available
ChEBI ID16020
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [19212411 ]
  2. 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. [15116424 ]
  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. [9129323 ]
  4. Uziel M, Smith LH, Taylor SA: Modified nucleosides in urine: selective removal and analysis. Clin Chem. 1976 Sep;22(9):1451-5. [954194 ]
  5. 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. [1739950 ]
  6. 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. [15991285 ]
  7. Takahashi R, Shiono T, Tamai M, Itoh K, Mizugaki M: [Expression of modified nucleoside, 1-methyladenosine in intraocular tumors and the retinas]. Nihon Ganka Gakkai Zasshi. 1993 Jan;97(1):43-9. [8434538 ]