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Identification
YMDB IDYMDB00510
NameInosine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionInosine, also known as hypoxanthosine or panholic-L, 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. Inosine is a moderately basic compound (based on its pKa). Inosine exists in all living species, ranging from bacteria to humans. Inosine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (-)-Inosine
  • 1,9-dihydro-9-b-D-ribofuranosyl-6H-Purin-6-one
  • 1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one
  • 1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one
  • 9-b-D-ribofuranosyl-Hypoxanthine
  • 9-b-D-Ribofuranosylhypoxanthine
  • 9-beta-D-ribofuranosyl-Hypoxanthine
  • 9-beta-D-Ribofuranosylhypoxanthine
  • 9-beta-delta-ribofuranosyl-Hypoxanthine
  • 9-beta-delta-Ribofuranosylhypoxanthine
  • 9beta-D-Ribofuranosylhypoxanthine
  • 9beta-delta-Ribofuranosylhypoxanthine
  • Atorel
  • beta-D-Ribofuranoside hypoxanthine-9
  • beta-delta-Ribofuranoside hypoxanthine-9
  • beta-Inosine
  • HXR
  • Hypoxanthine 9-beta-D-ribofuranoside
  • Hypoxanthine 9-beta-delta-ribofuranoside
  • Hypoxanthine D-riboside
  • Hypoxanthine nucleoside
  • Hypoxanthine ribonucleoside
  • Hypoxanthine riboside
  • hypoxanthine-9 beta-D-Ribofuranoside
  • hypoxanthine-9 beta-delta-Ribofuranoside
  • Hypoxanthine-9-beta-D-ribofuranoside
  • Hypoxanthine-9-beta-delta-ribofuranoside
  • Hypoxanthine-9-D-ribofuranoside
  • Hypoxanthine-9-delta-ribofuranoside
  • hypoxanthine-ribose
  • Hypoxanthosine
  • Indole-3-carboxaldehyde
  • Ino
  • Inosie
  • iso-prinosine
  • Oxiamin
  • Panholic-L
  • Pantholic-L
  • Ribonosine
  • Selfer
  • Trophicardyl
  • 9-beta-D-Ribofuranosyl-9H-purin-6-ol
  • i
  • Inosin
  • Inosina
  • Inosinum
  • Inotin
  • 9-b-D-Ribofuranosyl-9H-purin-6-ol
  • 9-Β-D-ribofuranosyl-9H-purin-6-ol
  • 9-Β-D-ribofuranosylhypoxanthine
CAS number58-63-9
WeightAverage: 268.2261
Monoisotopic: 268.080769514
InChI KeyUGQMRVRMYYASKQ-KQYNXXCUSA-N
InChIInChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
IUPAC Name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
Traditional IUPAC Nameinosine
Chemical FormulaC10H12N4O5
SMILESOC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12
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-oxopurine
  • Hypoxanthine
  • Pentose monosaccharide
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point218 °C
Experimental Properties
PropertyValueReference
Water Solubility15.8 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-2.10 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
logP-2ChemAxon
pKa (Strongest Acidic)6.94ChemAxon
pKa (Strongest Basic)2.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.9 m³·mol⁻¹ChemAxon
Polarizability24.6 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
Inosinic acid + waterphosphate + Inosine
Adenosine + water + hydronAmmonium + Inosine
Adenosine triphosphate + InosineInosinic acid + hydron + ADP
phosphate + InosineHypoxanthine + Ribose 1-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0frt-0890000000-c0c5ebc2bbf12c1a7edfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-00di-9440000000-566aadb777ee03fb22fbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fsi-1690000000-364bf8794afeeff6ba51JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0frt-0890000000-c0c5ebc2bbf12c1a7edfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9440000000-566aadb777ee03fb22fbJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fsi-1690000000-364bf8794afeeff6ba51JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-9250000000-d6ee10ae0804bda3e4ceJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0lmr-8659500000-9f567e118aa09e880541JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-012b2024bf3b3837c54cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0900000000-08a2204bd9dd4d300b73JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-2900000000-8da9aa27b202f672fb83JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0930000000-ee37a7516ef378cd665dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0900000000-e0575da4ae91163a2a90JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-379f5383e1bd290db9b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0900000000-cd539725f09d01a39e25JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uxr-0930000000-b69310182305cd88dbc5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00l2-9300000000-65a24aadb3a2b262cacfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-9c77149cd916c0340573JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-e8f9aac2c9bfc820dc7dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014r-0490020000-6eeacbf0ca8726ed8542JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9100000000-cdcc2e477ba37ca8f07aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-f96733a8f63a90d3644dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0900000000-b9b05cbee9a42ce87c0fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-015i-0696011000-c836d8cd13395c898ae1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9100000000-d8c6fdb9231ac2c6e939JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-632ba91cd477e5aaf9e5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-fc11279b73334e4ea0a8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0090000000-00981efb4a9571473866JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0390000000-989ff580a7b60b151996JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0920000000-b78cba83cbf8f1ae48f3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-000i-0910000000-505a6507fcb525fe9a14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-052r-2900000000-33d1372d34f6b06e3a2fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-0900000000-a0601a44cbbc12888cc2JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Itoh, R., Saint-Marc, C., Chaignepain, S., Katahira, R., Schmitter, J. M., Daignan-Fornier, B. (2003). "The yeast ISN1 (YOR155c) gene encodes a new type of IMP-specific 5'-nucleotidase." BMC Biochem 4:4.12735798
Synthesis Reference:Shi, Qingshan; Qiu, Yutang; Li, Liangqiu; Lin, Xiaoping. New inosine-producing bacterium and method for producing inosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp.
External Links:
ResourceLink
CHEBI ID17596
HMDB IDHMDB00195
Pubchem Compound ID6021
Kegg IDC00294
ChemSpider ID5799
FOODB IDFDB011802
WikipediaInosine
BioCyc IDINOSINE

Enzymes

General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
PNP1
Uniprot ID:
Q05788
Molecular weight:
33754.60156
Reactions
Purine nucleoside + phosphate → purine + alpha-D-ribose 1-phosphate.
General function:
Involved in deaminase activity
Specific function:
Adenosine + H(2)O = inosine + NH(3)
Gene Name:
AAH1
Uniprot ID:
P53909
Molecular weight:
39634.69922
Reactions
Adenosine + H(2)O → inosine + NH(3).
General function:
Involved in magnesium ion binding
Specific function:
IMP-specific 5'-nucleotidase involved in IMP (inositol monophosphate) degradation
Gene Name:
ISN1
Uniprot ID:
Q99312
Molecular weight:
51329.5
Reactions