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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-01-29 12:09:56 UTC
Update Date2020-10-09 21:08:19 UTC
HMDB IDHMDB0011599
Secondary Accession Numbers
  • HMDB11599
Metabolite Identification
Common Name1-Methyladenine
Description1-Methyladenine belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 1-Methyladenine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 1-methyladenine a potential biomarker for the consumption of these foods. 1-Methyladenine 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. 1-Methyladenine, with regard to humans, has been linked to the inborn metabolic disorder adenosine deaminase deficiency. Based on a literature review a significant number of articles have been published on 1-Methyladenine.
Structure
Data?1582752927
Synonyms
ValueSource
N1-MethyladenineChEBI
1, 9-dihydro-1-Methyl-6H-purin-6-imineHMDB
1-Methyl-1H-purin-6-amineHMDB
1-Methyl-1H-purin-6-ylamineHMDB
1-Methyl-adenineHMDB
Chemical FormulaC6H7N5
Average Molecular Weight149.1533
Monoisotopic Molecular Weight149.070145249
IUPAC Name1-methyl-1H-purin-6-amine
Traditional Name1-methyl-1H-purin-6-amine
CAS Registry Number5142-22-3
SMILES
CN1C=NC2=NC=NC2=C1N
InChI Identifier
InChI=1S/C6H7N5/c1-11-3-10-6-4(5(11)7)8-2-9-6/h2-3H,7H2,1H3
InChI KeyHPZMWTNATZPBIH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker130.96730932474
[M+H]+Baker128.35330932474
[M-H]-Not Available130.967http://allccs.zhulab.cn/database/detail?ID=AllCCS00001787
[M+H]+Not Available128.353http://allccs.zhulab.cn/database/detail?ID=AllCCS00001787
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.91 g/LALOGPS
logP10(-1.2) g/LALOGPS
logP10(-0.5) g/LChemAxon
logS10(-1.9) g/LALOGPS
pKa (Strongest Basic)0.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.81 m³·mol⁻¹ChemAxon
Polarizability14.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.98831661259
DarkChem[M-H]-128.22931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-MethyladenineCN1C=NC2=NC=NC2=C1N2399.4Standard polar33892256
1-MethyladenineCN1C=NC2=NC=NC2=C1N1620.0Standard non polar33892256
1-MethyladenineCN1C=NC2=NC=NC2=C1N1932.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Methyladenine,1TMS,isomer #1CN1C=NC2=NC=NC2=C1N[Si](C)(C)C2022.7Semi standard non polar33892256
1-Methyladenine,1TMS,isomer #1CN1C=NC2=NC=NC2=C1N[Si](C)(C)C1830.9Standard non polar33892256
1-Methyladenine,1TMS,isomer #1CN1C=NC2=NC=NC2=C1N[Si](C)(C)C2825.7Standard polar33892256
1-Methyladenine,2TMS,isomer #1CN1C=NC2=NC=NC2=C1N([Si](C)(C)C)[Si](C)(C)C1892.5Semi standard non polar33892256
1-Methyladenine,2TMS,isomer #1CN1C=NC2=NC=NC2=C1N([Si](C)(C)C)[Si](C)(C)C1915.7Standard non polar33892256
1-Methyladenine,2TMS,isomer #1CN1C=NC2=NC=NC2=C1N([Si](C)(C)C)[Si](C)(C)C2492.0Standard polar33892256
1-Methyladenine,1TBDMS,isomer #1CN1C=NC2=NC=NC2=C1N[Si](C)(C)C(C)(C)C2242.9Semi standard non polar33892256
1-Methyladenine,1TBDMS,isomer #1CN1C=NC2=NC=NC2=C1N[Si](C)(C)C(C)(C)C2024.9Standard non polar33892256
1-Methyladenine,1TBDMS,isomer #1CN1C=NC2=NC=NC2=C1N[Si](C)(C)C(C)(C)C2892.2Standard polar33892256
1-Methyladenine,2TBDMS,isomer #1CN1C=NC2=NC=NC2=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2295.2Semi standard non polar33892256
1-Methyladenine,2TBDMS,isomer #1CN1C=NC2=NC=NC2=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2333.7Standard non polar33892256
1-Methyladenine,2TBDMS,isomer #1CN1C=NC2=NC=NC2=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2587.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Methyladenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-4900000000-f072057fd2e79f405bb42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Methyladenine 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 - 1-Methyladenine 10V, Positive-QTOFsplash10-0udi-0900000000-5c8b7b78cfeaed4800692016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 20V, Positive-QTOFsplash10-0udi-0900000000-43ecee09f3839868d64a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 40V, Positive-QTOFsplash10-05fu-9500000000-25484796e092978955322016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 10V, Negative-QTOFsplash10-0002-0900000000-481001363707d4d472252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 20V, Negative-QTOFsplash10-0002-1900000000-527244488c433cfa02fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 40V, Negative-QTOFsplash10-0a6r-8900000000-69922974e3706889c4e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 10V, Positive-QTOFsplash10-0udi-0900000000-18eefbc35459f26a65702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 20V, Positive-QTOFsplash10-0udi-0900000000-08f7fc5284c0958707912021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 40V, Positive-QTOFsplash10-05mo-9500000000-fd2c2110ae89bb30148c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 10V, Negative-QTOFsplash10-0002-0900000000-0fdae69660ea9759916e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 20V, Negative-QTOFsplash10-0002-1900000000-dfd1a46d01dc7bda7e562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Methyladenine 40V, Negative-QTOFsplash10-0536-9600000000-f6310b9904ad41cab6ee2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.1 (0.0-0.20) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified3.15 umol/mmol creatinineAdult (>18 years old)FemaleAdenosine deaminase(ADA) deficiency details
Associated Disorders and Diseases
Disease References
Adenosine deaminase deficiency
  1. Mills GC: 1-Methyladenine in urine of an adenosine deaminase-deficient adult without immunodeficiency. Biochem Med Metab Biol. 1989 Dec;42(3):240-7. [PubMed:2597438 ]
Associated OMIM IDs
  • 102700 (Adenosine deaminase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028310
KNApSAcK IDNot Available
Chemspider ID71157
KEGG Compound IDC02216
BioCyc ID1-METHYLADENINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78821
PDB IDNot Available
ChEBI ID18083
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000843
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Falnes PO: Repair of 3-methylthymine and 1-methylguanine lesions by bacterial and human AlkB proteins. Nucleic Acids Res. 2004 Dec 1;32(21):6260-7. Print 2004. [PubMed:15576352 ]