Showing Compound Card for Isopentenyladenine-9-N-glucoside (CDB005019)

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Record Information
Version1.0
Created at2020-04-17 19:01:02 UTC
Updated at2020-11-18 16:39:13 UTC
CannabisDB IDCDB005019
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsopentenyladenine-9-N-glucoside
DescriptionIsopentenyl-Adenine-9-glucoside belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Isopentenyl-Adenine-9-glucoside is a strong basic compound (based on its pKa). Isopentenyladenine-9-N-glucoside is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
9-beta-D-Glucopyranosyl-N-(3-methyl-2-butenyl)-9H-purin-6-amineHMDB
9-Β-D-glucopyranosyl-N-(3-methyl-2-butenyl)-9H-purin-6-amineHMDB
Isopentenyladenine 9-glucosideHMDB
N6-(delta2-Isopentenyl)adenine N-glucosideHMDB
N6-(Δ2-isopentenyl)adenine N-glucosideHMDB
Isopentenyladenine-9-N-glucosideHMDB
Chemical FormulaC16H23N5O5
Average Molecular Weight365.39
Monoisotopic Molecular Weight365.1699
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxane-3,4,5-triol
Traditional Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{6-[(3-methylbut-2-en-1-yl)amino]purin-9-yl}oxane-3,4,5-triol
CAS Registry Number83087-94-9
SMILES
CC(C)=CCNC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C16H23N5O5/c1-8(2)3-4-17-14-10-15(19-6-18-14)21(7-20-10)16-13(25)12(24)11(23)9(5-22)26-16/h3,6-7,9,11-13,16,22-25H,4-5H2,1-2H3,(H,17,18,19)/t9-,11-,12+,13-,16-/m1/s1
InChI KeyXEHLLUQVSRLWMH-HDNYONAXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • N-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Monosaccharide
  • N-substituted imidazole
  • Oxane
  • Imidolactam
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Secondary amine
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.21ALOGPS
logP-1.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.36ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.78 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.77 m³·mol⁻¹ChemAxon
Polarizability37.21 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsopentenyladenine-9-N-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 14V, positivesplash10-0uxr-0298000000-0796a4748cda365375a32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 15V, positivesplash10-001i-0091000000-111dbb8a9b923cf92c742020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, positivesplash10-014i-0009000000-bebbf847d9187deac15d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 20V, positivesplash10-0udi-0491000000-1cf6947895c6e66fc7422020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 30V, positivesplash10-000i-0910000000-13e448d15e73c5dddae32020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-417863da7287d5fde5dc2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0690000000-301d83d7a8957192b1422021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1920000000-41390f115adbb1270a6f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-98d4ae4ed30f00729bb82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-1294000000-7ffee300e1191b423e572021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-e12a92390408e0c807cc2021-09-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0012240
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028882
KNApSAcK IDC00007548
Chemspider ID9849735
KEGG Compound IDNot Available
BioCyc IDCPD-4603
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11675006
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available