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Identification
YMDB IDYMDB00352
NameInosinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionInosinic acid, also known as 5'-inosinate or 5'-IMP, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Inosinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Inosinic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 5'-IMP
  • 5'-Inosinate
  • 5'-Inosine monophosphate
  • 5'-Inosinic acid
  • IMP
  • Inosine 5'-monophosphate
  • Inosine 5'-phosphate
  • Inosine Monophosphate
  • Inosine-5'-monophosphate
  • 2'-Inosine-5'-monophosphate
  • Hypoxanthosine 5'-monophosphate
  • Ribosylhypoxanthine monophosphate
  • 2'-Inosine-5'-monophosphoric acid
  • 5'-Inosine monophosphoric acid
  • Hypoxanthosine 5'-monophosphoric acid
  • Inosine 5'-monophosphoric acid
  • Inosine 5'-phosphoric acid
  • Inosine monophosphoric acid
  • Ribosylhypoxanthine monophosphoric acid
  • Inosinate
  • Inosinic acids
  • Inosinate, sodium
  • monoPhosphate, inosine
  • monoPhosphate, ribosylhypoxanthine
  • Sodium inosinate
  • Acid, inosinic
  • Acids, inosinic
CAS number131-99-7
WeightAverage: 348.206
Monoisotopic: 348.047099924
InChI KeyGRSZFWQUAKGDAV-KQYNXXCUSA-N
InChIInChI=1S/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-6,9-dihydro-1H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Nameinosine-5'-monophosphate
Chemical FormulaC10H13N4O8P
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N1C([H])=NC2=C1N=C([H])N([H])C2=O)C([H])([H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Tetrahydrofuran
  • Vinylogous amide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.05 g/LALOGPS
logP-2ALOGPS
logP-2.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)0.51ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area175.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.2 m³·mol⁻¹ChemAxon
Polarizability29.14 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB021901
SMPDB Pathways
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB Reactions
GTP + Inosinic acid + L-Aspartic acidGuanosine diphosphate + phosphate + Adenylsuccinic acid
Inosinic acid + L-Aspartic acid + GTPGuanosine diphosphate + phosphate + hydron + N6-(1,2-Dicarboxyethyl)-AMP
FAICARInosinic acid + water
Inosinic acid + NAD + waterNADH + hydron + Xanthylic acid
KEGG Reactions
water + 3',5'-cyclic IMPInosinic acid + hydron
Inosinic acid + waterphosphate + Inosine
Adenosine monophosphate + water + hydronInosinic acid + Ammonium
GTP + Inosinic acid + L-Aspartic acidphosphate + hydron + Guanosine diphosphate + Adenylsuccinic acid
Hypoxanthine + Phosphoribosyl pyrophosphatePyrophosphate + Inosinic acid
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
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Hyle, J. W., Shaw, R. J., Reines, D. (2003). "Functional distinctions between IMP dehydrogenase genes in providing mycophenolate resistance and guanine prototrophy to yeast." J Biol Chem 278:28470-28478.12746440
  • 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:Park, Yeong Hun; Cho, Gwang Myeong; Baek, Min Ji; Hong, Guk Gi; Lee, Jin Nam. Method for preparing 5'-inosinic acid by using microbe capable of over-expressing purC gene. Repub. Korea (2007), 7pp.
External Links:
ResourceLink
CHEBI ID17202
HMDB IDHMDB00175
Pubchem Compound ID8582
Kegg IDC00130
ChemSpider ID8264
FOODB IDFDB021901
WikipediaInosinic_acid
BioCyc IDIMP

Enzymes

General function:
Involved in adenylosuccinate synthase activity
Specific function:
Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first commited step in the biosynthesis of AMP from IMP
Gene Name:
ADE12
Uniprot ID:
P80210
Molecular weight:
48279.10156
Reactions
GTP + IMP + L-aspartate → GDP + phosphate + N(6)-(1,2-dicarboxyethyl)-AMP.
General function:
Involved in IMP cyclohydrolase activity
Specific function:
10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Gene Name:
ADE17
Uniprot ID:
P38009
Molecular weight:
65262.60156
Reactions
10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide → tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
IMP + H(2)O → 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
General function:
Involved in IMP cyclohydrolase activity
Specific function:
10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Gene Name:
ADE16
Uniprot ID:
P54113
Molecular weight:
65281.80078
Reactions
10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide → tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
IMP + H(2)O → 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
General function:
Involved in deaminase activity
Specific function:
AMP deaminase plays a critical role in energy metabolism
Gene Name:
AMD1
Uniprot ID:
P15274
Molecular weight:
93300.79688
Reactions
AMP + H(2)O → IMP + NH(3).
General function:
Involved in catalytic activity
Specific function:
Controls the level of cAMP in yeast cells, together with the low-affinity cAMP phosphodiesterase (PDE1)
Gene Name:
PDE2
Uniprot ID:
P06776
Molecular weight:
60999.19922
Reactions
Adenosine 3',5'-cyclic phosphate + H(2)O → adenosine 5'-phosphate.
General function:
Involved in catalytic activity
Specific function:
Inosine 5'-phosphate + NAD(+) + H(2)O = xanthosine 5'-phosphate + NADH
Gene Name:
IMD4
Uniprot ID:
P50094
Molecular weight:
56393.5
Reactions
Inosine 5'-phosphate + NAD(+) + H(2)O → xanthosine 5'-phosphate + NADH.
General function:
Involved in catalytic activity
Specific function:
Inosine 5'-phosphate + NAD(+) + H(2)O = xanthosine 5'-phosphate + NADH
Gene Name:
IMD3
Uniprot ID:
P50095
Molecular weight:
56584.39844
Reactions
Inosine 5'-phosphate + NAD(+) + H(2)O → xanthosine 5'-phosphate + NADH.
General function:
Involved in catalytic activity
Specific function:
Inosine 5'-phosphate + NAD(+) + H(2)O = xanthosine 5'-phosphate + NADH
Gene Name:
IMD2
Uniprot ID:
P38697
Molecular weight:
56529.5
Reactions
Inosine 5'-phosphate + NAD(+) + H(2)O → xanthosine 5'-phosphate + NADH.
General function:
Involved in catalytic activity
Specific function:
Inosine 5'-phosphate + NAD(+) + H(2)O = xanthosine 5'-phosphate + NADH
Gene Name:
IMD1
Uniprot ID:
P39567
Molecular weight:
44385.80078
Reactions
Inosine 5'-phosphate + NAD(+) + H(2)O → xanthosine 5'-phosphate + NADH.
General function:
Involved in nucleoside metabolic process
Specific function:
IMP + diphosphate = hypoxanthine + 5-phospho- alpha-D-ribose 1-diphosphate
Gene Name:
HPT1
Uniprot ID:
Q04178
Molecular weight:
25190.5
Reactions
IMP + diphosphate → hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate.
GMP + diphosphate → guanine + 5-phospho-alpha-D-ribose 1-diphosphate.
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