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Record Information
Version1.0
Creation Date2016-07-13 19:40:35 UTC
Update Date2016-07-20 21:03:03 UTC
LmdbLMDB00019
Secondary Accession NumbersNone
Metabolite Identification
Common NameAdenosine
DescriptionAdenosine, also known as adenocard or ade-rib, 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. A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. Adenosine is a drug which is used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (pvst), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (svt). also used as an adjunct to thallous chloride ti 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex svt. Adenosine is a strong basic compound (based on its pKa). Adenosine exists in all living species, ranging from bacteria to humans. Within humans, adenosine participates in a number of enzymatic reactions. In particular, adenosine can be converted into inosine; which is mediated by the enzyme adenosine deaminase. In addition, adenosine can be converted into adenine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. In humans, adenosine is involved in thioguanine action pathway. Outside of the human body, Adenosine is found, on average, in the highest concentration within beers and milk (cow). Adenosine has also been detected, but not quantified in, several different foods, such as capers, new zealand spinachs, welsh onions, hickory nuts, and pepper (spice). This could make adenosine a potential biomarker for the consumption of these foods. Adenosine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diolChEBI
6-Amino-9-beta-D-ribofuranosyl-9H-purineChEBI
9-beta-D-RibofuranosidoadenineChEBI
9-beta-D-Ribofuranosyl-9H-purin-6-amineChEBI
Ade-ribChEBI
Adenine deoxyribonucleosideChEBI
AdenocardChEBI
AdenocorChEBI
AdenoscanChEBI
AdenosinChEBI
AdenyldeoxyribosideChEBI
AdoChEBI
beta-D-AdenosineChEBI
DeoxyadenosineChEBI
DesoxyadenosineChEBI
6-Amino-9-b-D-ribofuranosyl-9H-purineGenerator
6-Amino-9-β-D-ribofuranosyl-9H-purineGenerator
9-b-D-RibofuranosidoadenineGenerator
9-Β-D-ribofuranosidoadenineGenerator
9-b-D-Ribofuranosyl-9H-purin-6-amineGenerator
9-Β-D-ribofuranosyl-9H-purin-6-amineGenerator
b-D-AdenosineGenerator
Β-D-adenosineGenerator
1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-ribofuranoseHMDB
1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-delta-ribofuranoseHMDB
6-Amino-9beta-D-ribofuranosyl-9H-purineHMDB
6-Amino-9beta-delta-ribofuranosyl-9H-purineHMDB
9-beta-D-ArabinofuranosyladenineHMDB
9-beta-D-RibofuranosyladenineHMDB
9-beta-delta-ArabinofuranosyladenineHMDB
9-beta-delta-RibofuranosidoadenineHMDB
9-beta-delta-Ribofuranosyl-9H-purin-6-amineHMDB
9-beta-delta-RibofuranosyladenineHMDB
9beta-D-Ribofuranosyl-9H-purin-6-amineHMDB
9beta-D-RibofuranosyladenineHMDB
9beta-delta-Ribofuranosyl-9H-purin-6-amineHMDB
9beta-delta-RibofuranosyladenineHMDB
Adenine nucleosideHMDB
Adenine ribosideHMDB
Adenine-9beta-D-ribofuranosideHMDB
Adenine-9beta-delta-ribofuranosideHMDB
beta-AdenosineHMDB
beta-delta-AdenosineHMDB
BonitonHMDB
MyocolHMDB
NucleocardylHMDB
SandesinHMDB
Chemical FormulaC10H13N5O4
Average Molecular Weight267.2413
Monoisotopic Molecular Weight267.096753929
IUPAC Name(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional Nameadenosine
CAS Registry Number58-61-7
SMILES
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1
InChI Identifier
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChI KeyOIRDTQYFTABQOQ-KQYNXXCUSA-N
Chemical Taxonomy
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-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Amine
  • Primary alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot 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-1.2ALOGPS
logP-2.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.54 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.2 m³·mol⁻¹ChemAxon
Polarizability25.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0f7w-1890000000-5c70a5423faa5e8eceafSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-001v-0691000000-8f88854b7d5adec5c558Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-001s-0790000000-cc3bcd977e11efd4ea25Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9460000000-3ae19bfaa5d2df72f9b1Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0gc0-0590000000-05874cecded3009c1f4dSpectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fsv-1792000000-b37fd6826f28aaf9e825Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7w-1890000000-5c70a5423faa5e8eceafSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001v-0691000000-8f88854b7d5adec5c558Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-001s-0790000000-cc3bcd977e11efd4ea25Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9460000000-3ae19bfaa5d2df72f9b1Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gc0-0590000000-05874cecded3009c1f4dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fsv-1792000000-b37fd6826f28aaf9e825Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4v-9560000000-986f3b1dfa5d898ed7a2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01c4-6912500000-ae103f43432726c1ad22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0940000000-da71247788bf1ba222e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0920000000-f2e8ec028abdd674b5e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-0910000000-815ed65588c07415cd65Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-1910000000-2780e737da8848411c4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-053r-1900000000-c6c1128990661334c15bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0910000000-35f90965f1f3c2b3236bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0910000000-65268017a112bc263b5eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0900000000-375c0e137f7068cf49afSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0900000000-ad5db8e5cbaacc341347Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0900000000-718be441310a581854a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0900000000-765c0fccf80d24951ef9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-053r-2900000000-2f0ca594f7cc031e54e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0940000000-da71247788bf1ba222e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0920000000-f2e8ec028abdd674b5e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0910000000-815ed65588c07415cd65Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1910000000-bbdd67de0fcb7c302c8fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-053r-1900000000-2c12434eaabba59a0a6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0910000000-35f90965f1f3c2b3236bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0980000000-56af5755b924f7c42369Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0980000000-25acc7da5b6ea2bee529Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-3900000000-602d3adcf68051f2992dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-4900000000-85777953862ffa85a828Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-8c7c25ea99344e167af5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0090000000-2de6609bcaad91b510b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-0f76e400a56cad0d0fcaSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Colostrum
  • Meat
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • S. F. Graham, T. ...
details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
DrugBank IDDB00640
HMDB IDHMDB0000050
FooDB IDFDB003554
Phenol Explorer IDNot Available
KNApSAcK IDC00007444
BiGG ID34273
BioCyc IDADENOSINE
METLIN ID86
PDB IDNot Available
Wikipedia LinkAdenosine
Chemspider ID54923
ChEBI ID16335
PubChem Compound ID60961
Kegg Compound IDC00212
YMDB IDYMDB00058
ECMDB IDECMDB00050
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available