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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
Water Solubility14.3 g/LALOGPS
logP-1.7ALOGPS
logP-2ChemAxon
logS-1.3ALOGPS
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
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