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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:47 UTC
Update Date2018-03-12 22:00:37 UTC
HMDB IDHMDB0029956
Secondary Accession Numbers
  • HMDB29956
Metabolite Identification
Common NameNebularine
DescriptionNebularine, also known as purine riboside is found in mushrooms. Nebularine can be isolated from the mushroom Clitocybe nebularis (clouded agaric). Nebularine is a nucleoside analog that is used in a variety of enzyme studies.
Structure
Thumb
Synonyms
ValueSource
1FKWHMDB
3-DeazaadenosineHMDB
9-(beta -D-Ribofuranosyl)purineHMDB
9-(beta-D-Ribofuranosyl)-9H-purineHMDB
9-(beta-D-Ribofuranosyl)purineHMDB
9-b-D-Ribofuranosyl-9H-purine, 9ci, 8ciHMDB
9-beta -RibofuranosylpurineHMDB
9-beta-D-Ribofuranosyl-9H-purineHMDB
9-beta-RibofuranosylpurineHMDB
9-Purine ribonucleosideHMDB
9beta-D-Ribofuranosyl-9H-purineHMDB
N-D-RibosylpurineHMDB
Nebularin (e)HMDB
Nebularin e)HMDB
Nebularin(e)HMDB
PURHMDB
Purine nucleosideHMDB
Purine ribonucleosideHMDB
Purine ribosideHMDB
Purine-1-D-ribofuranosideHMDB
Purine-9-beta-D-ribofuranosideHMDB
PurinosineHMDB
Ribosyl-isopurineHMDB
Ribosyl-purineHMDB
RibosylpurineHMDB
Chemical FormulaC10H12N4O4
Average Molecular Weight252.2267
Monoisotopic Molecular Weight252.085854892
IUPAC Name2-(hydroxymethyl)-5-(9H-purin-9-yl)oxolane-3,4-diol
Traditional Namenebularine
CAS Registry Number550-33-4
SMILES
OCC1OC(C(O)C1O)N1C=NC2=C1N=CN=C2
InChI Identifier
InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2
InChI KeyMRWXACSTFXYYMV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine nucleosides. These 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
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Primary alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point182 - 183 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility100 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.8 g/LALOGPS
logP-0.99ALOGPS
logP-1.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.18 m³·mol⁻¹ChemAxon
Polarizability23.46 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05c6-9320000000-8568cb65887589a7c24cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0umr-6549300000-2f2e367dec1b5b795a90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0079-0900000000-56dbcaa78636ebb05d35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0079-0900000000-88d4f77072df7340a924View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00y0-0900000000-e3a077bcd64184c0debaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0940000000-558c13580fe37e7be7ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-15f6248a2b75854f25d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9800000000-6bd857bf607d73c94c21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0790000000-52cdec17cf806f6a8d60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-28abc2355f386333f114View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-fb33005da35ddacd66d1View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001236
KNApSAcK IDC00018685
Chemspider ID217498
KEGG Compound IDC01736
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound248425
PDB IDNot Available
ChEBI ID139743
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in deaminase activity
Specific function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:
ADA
Uniprot ID:
P00813
Molecular weight:
40764.13
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69
Reactions
Nebularine + Phosphoric acid → Purine + Ribose 1-phosphatedetails