Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:01 UTC
HMDB IDHMDB00175
Secondary Accession NumbersNone
Metabolite Identification
Common NameInosinic acid
DescriptionInosinic acid is a purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety. Inosinic acid is a nucleotide present in muscle and other tissues. It is formed by the deamination of AMP and when hydrolysed produces inosine. Inosinic acid is the ribonucleotide of hypoxanthine and is the first compound formed during the synthesis of purine. (Wikipedia).
Structure
Thumb
Synonyms
  1. 5'-IMP
  2. 5'-Inosinate
  3. 5'-Inosine monophosphate
  4. 5'-Inosinic acid
  5. IMP
  6. Inosine 5'-monophosphate
  7. Inosine 5'-phosphate
  8. Inosine Monophosphate
  9. Inosine-5'-monophosphate
Chemical FormulaC10H13N4O8P
Average Molecular Weight348.206
Monoisotopic Molecular Weight348.047099924
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 Name[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number131-99-7
SMILES
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CNC2=O
InChI Identifier
InChI=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
InChI KeyGRSZFWQUAKGDAV-KQYNXXCUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • inosine phosphate(ChEBI)
  • purine ribonucleoside 5'-monophosphate(ChEBI)
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside Monophosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Alanine and aspartate metabolism
  • Component of Purine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area175.73ChemAxon
rotatable bond count4ChemAxon
refractivity72.2ChemAxon
polarizability29.14ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • All Tissues
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified63.0 +/- 41.0 uMAdult (>18 years old)BothNormal
Cellular CytoplasmDetected and Quantified10 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified3.19 (0.00 +/- 19.70) uMAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified2.31(0.00-41.40) uMAdult (>18 years old)BothSimple ffebrile seizures
Cerebrospinal Fluid (CSF)Detected and Quantified2.48 (0.00 +/- 27.20) uMAdult (>18 years old)BothComplex febrile seizures
Associated Disorders and Diseases
Disease References
Febrile seizures
  • Rodriguez-Nunez A, Cid E, Rodriguez-Garcia J, Camina F, Rodriguez-Segade S, Castro-Gago M: Cerebrospinal fluid purine metabolite and neuron-specific enolase concentrations after febrile seizures. Brain Dev. 2000 Oct;22(7):427-31. Pubmed: 11102727
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021901
KNApSAcK IDNot Available
Chemspider ID8264
KEGG Compound IDC00130
BioCyc IDIMP
BiGG ID33960
Wikipedia LinkInosinic acid
NuGOwiki LinkHMDB00175
Metagene LinkHMDB00175
METLIN ID5196
PubChem Compound8582
PDB IDIMP
ChEBI ID17202
References
Synthesis ReferencePark, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  2. McConell GK, Shinewell J, Stephens TJ, Stathis CG, Canny BJ, Snow RJ: Creatine supplementation reduces muscle inosine monophosphate during endurance exercise in humans. Med Sci Sports Exerc. 2005 Dec;37(12):2054-61. Pubmed: 16331129
  3. Castro-Gago M, Cid E, Trabazo S, Pavon P, Camina F, Rodriguez-Segade S, Einis Punal J, Rodriguez-Nunez A: Cerebrospinal fluid purine metabolites and pyrimidine bases after brief febrile convulsions. Epilepsia. 1995 May;36(5):471-4. Pubmed: 7614924
  4. Green HJ, Grant SM, Phillips SM, Enns DL, Tarnopolsky MA, Sutton JR: Reduced muscle lactate during prolonged exercise following induced plasma volume expansion. Can J Physiol Pharmacol. 1997 Dec;75(12):1280-6. Pubmed: 9534937
  5. Rodriguez-Nunez A, Cid E, Rodriguez-Garcia J, Camina F, Rodriguez-Segade S, Castro-Gago M: Concentrations of nucleotides, nucleosides, purine bases, oxypurines, uric acid, and neuron-specific enolase in the cerebrospinal fluid of children with sepsis. J Child Neurol. 2001 Sep;16(9):704-6. Pubmed: 11575617
  6. Pouw EM, Schols AM, van der Vusse GJ, Wouters EF: Elevated inosine monophosphate levels in resting muscle of patients with stable chronic obstructive pulmonary disease. Am J Respir Crit Care Med. 1998 Feb;157(2):453-7. Pubmed: 9476857
  7. Allison AC, Eugui EM: Purine metabolism and immunosuppressive effects of mycophenolate mofetil (MMF). Clin Transplant. 1996 Feb;10(1 Pt 2):77-84. Pubmed: 8680053
  8. van Hall G, van der Vusse GJ, Soderlund K, Wagenmakers AJ: Deamination of amino acids as a source for ammonia production in human skeletal muscle during prolonged exercise. J Physiol. 1995 Nov 15;489 ( Pt 1):251-61. Pubmed: 8583409
  9. McConell G, Snow RJ, Proietto J, Hargreaves M: Muscle metabolism during prolonged exercise in humans: influence of carbohydrate availability. J Appl Physiol. 1999 Sep;87(3):1083-6. Pubmed: 10484580
  10. Klupp J, Pfitzmann R, Langrehr JM, Neuhaus P: Indications of mycophenolate mofetil in liver transplantation. Transplantation. 2005 Sep 27;80(1 Suppl):S142-6. Pubmed: 16286893
  11. Bangsbo J, Gollnick PD, Graham TE, Juel C, Kiens B, Mizuno M, Saltin B: Anaerobic energy production and O2 deficit-debt relationship during exhaustive exercise in humans. J Physiol. 1990 Mar;422:539-59. Pubmed: 2352192
  12. McCauley TG, Hamaguchi N, Stanton M: Aptamer-based biosensor arrays for detection and quantification of biological macromolecules. Anal Biochem. 2003 Aug 15;319(2):244-50. Pubmed: 12871718
  13. Rush JW, MacLean DA, Hultman E, Graham TE: Exercise causes branched-chain oxoacid dehydrogenase dephosphorylation but not AMP deaminase binding. J Appl Physiol. 1995 Jun;78(6):2193-200. Pubmed: 7665417
  14. McConell GK, Canny BJ, Daddo MC, Nance MJ, Snow RJ: Effect of carbohydrate ingestion on glucose kinetics and muscle metabolism during intense endurance exercise. J Appl Physiol. 2000 Nov;89(5):1690-8. Pubmed: 11053315
  15. Swart PJ, Beljaars E, Smit C, Pasma A, Schuitemaker H, Meijer DK: Comparative pharmacokinetic, immunologic and hematologic studies on the anti-HIV-1/2 compounds aconitylated and succinylated HSA. J Drug Target. 1996;4(2):109-16. Pubmed: 8894971
  16. Scott GS, Spitsin SV, Kean RB, Mikheeva T, Koprowski H, Hooper DC: Therapeutic intervention in experimental allergic encephalomyelitis by administration of uric acid precursors. Proc Natl Acad Sci U S A. 2002 Dec 10;99(25):16303-8. Epub 2002 Nov 25. Pubmed: 12451183

Enzymes

Gene Name:
NT5E
Uniprot ID:
P21589
Reactions
Inosinic acid + Water unknown Inosine + Phosphoric aciddetails
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Reactions
Inosinic acid + Water unknown Inosine + Phosphoric aciddetails
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Reactions
Inosinic acid + Water unknown Inosine + Phosphoric aciddetails
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Reactions
Inosinic acid + Water unknown Inosine + Phosphoric aciddetails
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Reactions
Inosinic acid + Water unknown Inosine + Phosphoric aciddetails
Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
IDP + Water unknown Inosinic acid + Phosphoric aciddetails
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Reactions
IDP + Water unknown Inosinic acid + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
IDP + Water unknown Inosinic acid + Phosphoric aciddetails
Gene Name:
PYGL
Uniprot ID:
P06737
Gene Name:
PYGM
Uniprot ID:
P11217
Gene Name:
PYGB
Uniprot ID:
P11216
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Reactions
Inosine triphosphate + Water unknown Inosinic acid + Pyrophosphatedetails
Gene Name:
HPRT1
Uniprot ID:
P00492
Reactions
Inosinic acid + Pyrophosphate unknown Hypoxanthine + Phosphoribosyl pyrophosphatedetails
Gene Name:
AMPD3
Uniprot ID:
Q01432
Reactions
Adenosine monophosphate + Water unknown Inosinic acid + Ammoniadetails
Gene Name:
AMPD2
Uniprot ID:
Q01433
Reactions
Adenosine monophosphate + Water unknown Inosinic acid + Ammoniadetails
Gene Name:
AMPD1
Uniprot ID:
P23109
Reactions
Adenosine monophosphate + Water unknown Inosinic acid + Ammoniadetails
Gene Name:
GMPR2
Uniprot ID:
Q9P2T1
Reactions
Inosinic acid + Ammonia + NADP unknown Guanosine monophosphate + NADPHdetails
Inosinic acid + Ammonia + NADP unknown Guanosine monophosphate + NADPH + Hydrogen Iondetails
Gene Name:
GMPR
Uniprot ID:
P36959
Reactions
Inosinic acid + Ammonia + NADP unknown Guanosine monophosphate + NADPHdetails
Inosinic acid + Ammonia + NADP unknown Guanosine monophosphate + NADPH + Hydrogen Iondetails
Gene Name:
ENTPD4
Uniprot ID:
Q9Y227
Reactions
IDP + Water unknown Inosinic acid + Phosphoric aciddetails
Gene Name:
ENTPD6
Uniprot ID:
O75354
Reactions
IDP + Water unknown Inosinic acid + Phosphoric aciddetails
Gene Name:
ENTPD5
Uniprot ID:
O75356
Reactions
IDP + Water unknown Inosinic acid + Phosphoric aciddetails
Gene Name:
ADSS
Uniprot ID:
P30520
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + N(6)-(1,2-dicarboxyethyl)AMPdetails
Gene Name:
IMPDH2
Uniprot ID:
P12268
Reactions
Inosinic acid + NAD + Water unknown Xanthylic acid + NADHdetails
Inosinic acid + NAD + Water unknown Xanthylic acid + NADH + Hydrogen Iondetails
Gene Name:
ATIC
Uniprot ID:
P31939
Reactions
Inosinic acid + Water unknown Phosphoribosyl formamidocarboxamidedetails
Gene Name:
IMPDH1
Uniprot ID:
P20839
Reactions
Inosinic acid + NAD + Water unknown Xanthylic acid + NADHdetails
Inosinic acid + NAD + Water unknown Xanthylic acid + NADH + Hydrogen Iondetails
Gene Name:
ADSSL1
Uniprot ID:
Q8N142
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + N(6)-(1,2-dicarboxyethyl)AMPdetails
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Reactions
Inosinic acid + Water unknown Inosine + Phosphoric aciddetails
Gene Name:
ENTPD4
Uniprot ID:
Q8NE73
Gene Name:
NT5C2
Uniprot ID:
P49902
Reactions
Inosinic acid + Water unknown Inosine + Phosphoric aciddetails
Gene Name:
IMPDH1
Uniprot ID:
A4D0Z6
Gene Name:
ENTPD8
Uniprot ID:
Q5MY95
Reactions
IDP + Water unknown Inosinic acid + Phosphoric aciddetails