Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-01-29 15:21:03 UTC
Update Date2023-02-21 17:17:29 UTC
HMDB IDHMDB0011614
Secondary Accession Numbers
  • HMDB11614
Metabolite Identification
Common Name7-Methyladenine
Description7-Methyladenine is part of the base excision repair pathway. In this pathway, alkylated DNA is hydrolysed via the enzyme DNA-3-methyladenine glycosylase II (EC 3.2.2.21), releasing 3-methyladenine, 3-methylguanine, 7-methylguanine and 7-methyladenine. This enzyme is responsible for the hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions. Base excision repair (BER) is a cellular mechanism that repairs damaged DNA throughout the cell cycle. Repairing DNA sequence errors is necessary so that mutations are not propagated or to remove lesions that may lead to breaks in the DNA during replication. Single bases in DNA can be chemically mutated, for example by deamination or alkylation, resulting in incorrect base-pairing, and consequently, mutations in the DNA. Base excision repair involves flipping the mutated base out of the DNA helix and repairing the base alone. There are two main enzymes used, DNA glycosylases and AP endonucleases. The DNA glycosylase is used to break the beta-N glycosidic bond to create an AP site. AP endonuclease recognizes this site and nicks the damaged DNA on the 5' side (upstream) of the AP site creating a free 3'-OH. DNA polymerase, Pol I (human pol beta), extends the DNA from the free 3'-OH using its exonuclease activity to replace the nucleotide of the damaged base, as well as a few downstream, followed by sealing of the new DNA strand by DNA ligase. In mammalian cells, this is done by LigIII in complex with the scaffold protein XRCC1. Usually, BER is divided into short-patch repair (where a single nucleotide is replaced) or long-patch repair (where 2-10 nucleotides are replaced). Mammalian long-patch repair includes PCNA and pol delta/epsilon for nucleotide resynthesis, FEN1 to cut of the 'flap' including the damaged base, and LigI.
Structure
Data?1676999849
Synonyms
ValueSource
7-MethyladenineChEMBL, HMDB
6-amino-7-MethylpurineHMDB
7-Methyl-7H-purin-6-amineHMDB
7-Methyl-7H-purin-6-amine (acd/name 4.0)HMDB
7-Methyl-7H-purin-6-ylamine (acd/name 4.0)HMDB
7-Methyl-N7-methyladenineHMDB
Chemical FormulaC6H7N5
Average Molecular Weight149.1533
Monoisotopic Molecular Weight149.070145249
IUPAC Name7-methyl-7H-purin-6-amine
Traditional Name7-methyladenine
CAS Registry Number935-69-3
SMILES
CN1C=NC2=NC=NC(N)=C12
InChI Identifier
InChI=1S/C6H7N5/c1-11-3-10-6-4(11)5(7)8-2-9-6/h2-3H,1H3,(H2,7,8,9)
InChI KeyHCGHYQLFMPXSDU-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
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Azacycle
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.66 g/LALOGPS
logP-0.09ALOGPS
logP-0.35ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.12 m³·mol⁻¹ChemAxon
Polarizability14.29 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]+128.98431661259
DarkChem[M-H]-128.22831661259
DeepCCS[M-2H]-162.67230932474
DeepCCS[M+Na]+137.99430932474
AllCCS[M+H]+132.432859911
AllCCS[M+H-H2O]+127.732859911
AllCCS[M+NH4]+136.732859911
AllCCS[M+Na]+137.932859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-129.632859911
AllCCS[M+HCOO]-130.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-MethyladenineCN1C=NC2=NC=NC(N)=C122337.7Standard polar33892256
7-MethyladenineCN1C=NC2=NC=NC(N)=C121750.7Standard non polar33892256
7-MethyladenineCN1C=NC2=NC=NC(N)=C121709.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-Methyladenine,1TMS,isomer #1CN1C=NC2=NC=NC(N[Si](C)(C)C)=C211903.6Semi standard non polar33892256
7-Methyladenine,1TMS,isomer #1CN1C=NC2=NC=NC(N[Si](C)(C)C)=C211772.8Standard non polar33892256
7-Methyladenine,1TMS,isomer #1CN1C=NC2=NC=NC(N[Si](C)(C)C)=C212766.1Standard polar33892256
7-Methyladenine,2TMS,isomer #1CN1C=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C211865.2Semi standard non polar33892256
7-Methyladenine,2TMS,isomer #1CN1C=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C211871.9Standard non polar33892256
7-Methyladenine,2TMS,isomer #1CN1C=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C212446.8Standard polar33892256
7-Methyladenine,1TBDMS,isomer #1CN1C=NC2=NC=NC(N[Si](C)(C)C(C)(C)C)=C212147.9Semi standard non polar33892256
7-Methyladenine,1TBDMS,isomer #1CN1C=NC2=NC=NC(N[Si](C)(C)C(C)(C)C)=C211933.2Standard non polar33892256
7-Methyladenine,1TBDMS,isomer #1CN1C=NC2=NC=NC(N[Si](C)(C)C(C)(C)C)=C212828.3Standard polar33892256
7-Methyladenine,2TBDMS,isomer #1CN1C=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C212246.4Semi standard non polar33892256
7-Methyladenine,2TBDMS,isomer #1CN1C=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C212277.4Standard non polar33892256
7-Methyladenine,2TBDMS,isomer #1CN1C=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C212545.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-Methyladenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-2900000000-e8c3a67ccd8c708bcc392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-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 - 7-Methyladenine 10V, Positive-QTOFsplash10-0udi-0900000000-4e05df90eeb217fb05432016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 20V, Positive-QTOFsplash10-0udi-0900000000-89d47c8d0ec0a29d619d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 40V, Positive-QTOFsplash10-00ea-9500000000-2f8613bd76fdc956419b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 10V, Negative-QTOFsplash10-0002-0900000000-77a0a50aa1ea18dfc6242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 20V, Negative-QTOFsplash10-0002-0900000000-9da281b20075d95cb8fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 40V, Negative-QTOFsplash10-060s-5900000000-7cb7767e9f0a843ef3f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 10V, Negative-QTOFsplash10-0002-0900000000-0fdae69660ea9759916e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 20V, Negative-QTOFsplash10-0002-0900000000-7e685a2f1c95c3ac528d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 40V, Negative-QTOFsplash10-014i-9300000000-f917c9f05153fdcd6add2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 10V, Positive-QTOFsplash10-0udi-0900000000-18eefbc35459f26a65702021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 20V, Positive-QTOFsplash10-0udi-0900000000-f25de4e35b83e75783bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Methyladenine 40V, Positive-QTOFsplash10-053r-9500000000-1fd51e3d79bd3456748f2021-09-23Wishart 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 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028319
KNApSAcK IDNot Available
Chemspider ID64663
KEGG Compound IDC02241
BioCyc IDCPD-13320
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71593
PDB IDNot Available
ChEBI ID28921
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions
Gene Name:
MPG
Uniprot ID:
P29372
Molecular weight:
32868.4