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Showing Compound isopentenyl adenosine (FDB030945)

Record Information
Version1.0
Creation date2015-05-07 20:34:51 UTC
Update date2019-11-26 03:21:58 UTC
Primary IDFDB030945
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameisopentenyl adenosine
DescriptionRiboprine, also known as isopentenyladenosine or ipa, is a member of the class of compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Riboprine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Riboprine can be found in a number of food items such as peppermint, chinese mustard, custard apple, and green bean, which makes riboprine a potential biomarker for the consumption of these food products.
CAS Number7724-76-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-IPAChEBI
2IPAChEBI
6-(3-Methyl-2-butenylamino)purine ribosideChEBI
6-(gamma,gamma-Dimethylallylamino)purine ribosideChEBI
i6aChEBI
IsopentenyladenosineChEBI
Isopentenyladenosine ribosideChEBI
N-(3-Methylbut-2-enyl)adenosineChEBI
N(6)-(2-Isopentenyl)adenosineChEBI
N(6)-(3-Methyl-2-butenyl)adenosineChEBI
RiboprinaChEBI
RiboprineChEBI
RiboprinumChEBI
6-(g,g-Dimethylallylamino)purine ribosideGenerator
6-(Γ,γ-dimethylallylamino)purine ribosideGenerator
N(6)-(delta(2)-Isopentenyl)adenosineMeSH
N-(3-Methyl-2-buten-1-yl)adenosinePhytoBank
2iPRPhytoBank
6-(2-Isopentenyl)adenosinePhytoBank
6-(3-Methyl-2-butenylamino)-9-beta-D-ribofuranosylpurinePhytoBank
6-(3-Methyl-2-butenylamino)-9-β-D-ribofuranosylpurinePhytoBank
6-(3-Methyl-2-butenylamino)-9-beta-ribofuranosylpurinePhytoBank
6-(3-Methyl-2-butenylamino)-9-β-ribofuranosylpurinePhytoBank
6-(3-Methyl-2-butenylamino)-beta,D-ribofuranosylpurinePhytoBank
6-(3-Methyl-2-butenylamino)-β,D-ribofuranosylpurinePhytoBank
IPAPhytoBank
Isopentenyladenine ribosidePhytoBank
N-(3-Methyl-2-butenyl)adenosinePhytoBank
N-IsopentenyladenosinePhytoBank
N6-(2-Isopentenyl)adenosinePhytoBank
N6-(3-Methyl-2-butenyl)adenosinePhytoBank
N6-(Dimethylallyl)adenosinePhytoBank
N6-(delta2-Isopentenyl)adenine ribosidePhytoBank
N6-(Δ2-Isopentenyl)adenine ribosidePhytoBank
N6-(delta2-Isopentenyl)adenosinePhytoBank
N6-(Δ2-Isopentenyl)adenosinePhytoBank
N6-(gamma,gamma-Dimethylallyl)adenosinePhytoBank
N6-(γ,γ-Dimethylallyl)adenosinePhytoBank
N6-IsopentenyladenosinePhytoBank
Isopentenyl adenosinePhytoBank
Predicted Properties
PropertyValueSource
Water Solubility4.23 g/LALOGPS
logP0.25ALOGPS
logP-0.43ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.55 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity87.81 m³·mol⁻¹ChemAxon
Polarizability34.1 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H21N5O4
IUPAC name(2R,3S,4R,5R)-2-(hydroxymethyl)-5-{6-[(3-methylbut-2-en-1-yl)amino]-9H-purin-9-yl}oxolane-3,4-diol
InChI IdentifierInChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
InChI KeyUSVMJSALORZVDV-SDBHATRESA-N
Isomeric SMILES[H][C@]1(CO)O[C@@]([H])(N2C=NC3=C(NCC=C(C)C)N=CN=C23)[C@]([H])(O)[C@]1([H])O
Average Molecular Weight335.3583
Monoisotopic Molecular Weight335.159354185
Classification
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides 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 nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Secondary amine
  • Oxacycle
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSisopentenyl adenosine, non-derivatized, GC-MS Spectrumsplash10-0w30-0960000000-0035fb65e8672a86a8e4Spectrum
GC-MSisopentenyl adenosine, non-derivatized, GC-MS Spectrumsplash10-001i-3980000000-8a77d79fb39101eb35b1Spectrum
GC-MSisopentenyl adenosine, non-derivatized, GC-MS Spectrumsplash10-00di-9740000000-fef11b9cca0d66b260ecSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f89-0971000000-8df58b6063424f35a1afSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f89-0961000000-e57cf833c2dc4f96fcc4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dl-0195000000-bb1c98cdfb4dd8bcbcf6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0291000000-5d247df3981e5a6e1e3bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0039000000-4b317606d25e8dde70f7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udr-0890000000-592e5a2a1e483e6e96c6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-ea249daf88f035efbbc9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000j-0921000000-aa0e302b67b3d15cc148Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1094000000-36a2ac96899c7345379bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5590000000-4ffae206d270237bc743Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-9640000000-998c5d223e675bf5ce87Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-1179000000-30ba1ff67a425cfbb2f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1390000000-4cb3ddc6acbd6135a3deSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1910000000-02115299433b6f3d4532Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0092000000-e8f3541125a895d0e198Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0690000000-c3d598e1b897f8be2f50Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1920000000-8336f37e1ca1564fa7a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0029000000-9c5472896f864fba8e44Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgi-1391000000-70044ff17099de729367Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-e42c4160c718b294fcefSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference