Showing Compound Card for 2-Aminopurine (CDB005714)

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Record Information
Version1.0
Created at2020-04-27 16:48:20 UTC
Updated at2021-01-04 18:49:11 UTC
CannabisDB IDCDB005714
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Aminopurine
Description2-Aminopurine, also known as 9H-purin-2-amine, belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. The parent compound of the 2-Aminopurines, comprising a purine core carrying an amino substituent at the 2-position. 2-Aminopurine is one of several structural isomers of aminopurine wherein the amino group is substituted at different positions around the purine ring. It is a purine analog of guanine and adenine and is used as a fluorescent molecular marker in nucleic acid research (PMID: 11120885 ). 2-Aminopurine most commonly pairs with thymine as an adenine-analogue but can also pair with cytosine as a guanine-analogue (PMID: 3461441 ). 2-Aminopurine is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1H-Purin-2-amineChEBI
2'-Amino-purineChEBI
2-Amino purineChEBI
2 AminopurineMeSH
Chemical FormulaC5H5N5
Average Molecular Weight135.13
Monoisotopic Molecular Weight135.0545
IUPAC Name2,3-dihydro-1H-purin-2-imine
Traditional Name2-aminopurine
CAS Registry Number452-06-2
SMILES
N=C1NC=C2N=CN=C2N1
InChI Identifier
InChI=1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
InChI KeyMWBWWFOAEOYUST-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.3ALOGPS
logP-1.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.54ChemAxon
pKa (Strongest Basic)5.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area72.63 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.23 m³·mol⁻¹ChemAxon
Polarizability12.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-Aminopurine, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Aminopurine, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Aminopurine, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Aminopurine, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Aminopurine, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Aminopurine, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Aminopurine, 3 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-Aminopurine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052r-5900000000-f54dbf15657fbe19ea84Spectrum
Predicted GC-MS2-Aminopurine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c1ee2199364d0258bae12021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-5c45352d5df81c74189a2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0apu-9300000000-be879c1905cfbd44d6c62021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-f69382028826abe575802021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-16ba32b77563d002c3252021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-9400000000-fc9d35094846175398c92021-10-12View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0245025
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9561
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Aminopurine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID479072
References
General References
  1. Jean JM, Hall KB: 2-Aminopurine fluorescence quenching and lifetimes: role of base stacking. Proc Natl Acad Sci U S A. 2001 Jan 2;98(1):37-41. doi: 10.1073/pnas.011442198. [PubMed:11120885 ]
  2. Sowers LC, Fazakerley GV, Eritja R, Kaplan BE, Goodman MF: Base pairing and mutagenesis: observation of a protonated base pair between 2-aminopurine and cytosine in an oligonucleotide by proton NMR. Proc Natl Acad Sci U S A. 1986 Aug;83(15):5434-8. doi: 10.1073/pnas.83.15.5434. [PubMed:3461441 ]