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Human Metabolome Database Version 3.5

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Showing metabocard for Inosinic acid (HMDB00175)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:01 -0700
HMDB ID HMDB00175
Secondary Accession Numbers None
Metabolite Identification
Common Name Inosinic acid
Description Inosinic 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H13N4O8P
Average Molecular Weight 348.206
Monoisotopic Molecular Weight 348.047099924
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 Number 131-99-7
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 Key GRSZFWQUAKGDAV-KQYNXXCUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine 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 Parent Purine Ribonucleoside Monophosphates
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Alanine and aspartate metabolism
  • Component of Purine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.05 g/L ALOGPS
LogP -2.04 ALOGPS
LogP -2.9 ChemAxon
LogS -2.06 ALOGPS
pKa (strongest acidic) 1.32 ChemAxon
pKa (strongest basic) 0.51 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 175.73 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 72.2 ChemAxon
Polarizability 29.14 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
MS/MS Spectrum GC-MS
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • All Tissues
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
63.0 +/- 41.0 uM Adult (>18 years old) Both Normal Not Available
Cellular Cytoplasm Detected and Quantified
Article_icon
10 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
3.19 (0.00 +/- 19.70) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
2.31(0.00-41.40) uM Adult (>18 years old) Both Simple ffebrile seizures Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
2.48 (0.00 +/- 27.20) uM Adult (>18 years old) Both Complex febrile seizures Not Available
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 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB021901
    KNApSAcK ID Not Available
    Chemspider ID 8264 Link_out
    KEGG Compound ID C00130 Link_out
    BioCyc ID IMP Link_out
    BiGG ID 33960 Link_out
    Wikipedia Link Inosinic acid Link_out
    NuGOwiki Link HMDB00175 Link_out
    Metagene Link HMDB00175 Link_out
    METLIN ID 5196 Link_out
    PubChem Compound 8582 Link_out
    PDB ID IMP Link_out
    ChEBI ID 17202 Link_out
    References
    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.
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. 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 Link_out
    2. 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 Link_out
    3. 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 Link_out
    4. 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 Link_out
    5. 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 Link_out
    6. 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 Link_out
    7. 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 Link_out
    8. 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 Link_out
    9. 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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    Enzymes
    Name: Cytosolic 5'-nucleotidase 1B
    Reactions:
    • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
    Gene Name: NT5C1B
    Uniprot ID: Q96P26 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cytosolic 5'-nucleotidase 1A
    Reactions:
    • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
    Gene Name: NT5C1A
    Uniprot ID: Q9BXI3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 5'(3')-deoxyribonucleotidase, cytosolic type
    Reactions:
      Gene Name: NT5C
      Uniprot ID: Q8TCD5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 5'(3')-deoxyribonucleotidase, mitochondrial
      Reactions:
        Gene Name: NT5M
        Uniprot ID: Q9NPB1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Ectonucleoside triphosphate diphosphohydrolase 1
        Reactions:
        • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
        Gene Name: ENTPD1
        Uniprot ID: P49961 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Soluble calcium-activated nucleotidase 1
        Reactions:
        • a nucleoside diphosphate + H2O = a nucleotide + phosphate [RN:R00329]
        Gene Name: CANT1
        Uniprot ID: Q8WVQ1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Ectonucleoside triphosphate diphosphohydrolase 3
        Reactions:
        • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
        Gene Name: ENTPD3
        Uniprot ID: O75355 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glycogen phosphorylase, liver form
        Reactions:
        • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
        Gene Name: PYGL
        Uniprot ID: P06737 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glycogen phosphorylase, muscle form
        Reactions:
        • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
        Gene Name: PYGM
        Uniprot ID: P11217 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glycogen phosphorylase, brain form
        Reactions:
        • [(1->4)-alpha-D-glucosyl]n + phosphate = [(1->4)-alpha-D-glucosyl]n-1 + alpha-D-glucose 1-phosphate [RN:R01821 R06050]
        Gene Name: PYGB
        Uniprot ID: P11216 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Inosine triphosphate pyrophosphatase
        Reactions:
        • a nucleoside triphosphate + H2O = a nucleotide + diphosphate [RN:R01532]
        Gene Name: ITPA
        Uniprot ID: Q9BY32 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Hypoxanthine-guanine phosphoribosyltransferase
        Reactions:
        • IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R01132]
        Gene Name: HPRT1
        Uniprot ID: P00492 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: AMP deaminase 3
        Reactions:
        • AMP + H2O = IMP + NH3 [RN:R00181]
        Gene Name: AMPD3
        Uniprot ID: Q01432 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: AMP deaminase 2
        Reactions:
        • AMP + H2O = IMP + NH3 [RN:R00181]
        Gene Name: AMPD2
        Uniprot ID: Q01433 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: AMP deaminase 1
        Reactions:
        • AMP + H2O = IMP + NH3 [RN:R00181]
        Gene Name: AMPD1
        Uniprot ID: P23109 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: GMP reductase 2
        Reactions:
        • inosine 5'-phosphate + NH3 + NADP+ = guanosine 5'-phosphate + NADPH + H+ [RN:R01134]
        Gene Name: GMPR2
        Uniprot ID: Q9P2T1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: GMP reductase 1
        Reactions:
        • inosine 5'-phosphate + NH3 + NADP+ = guanosine 5'-phosphate + NADPH + H+ [RN:R01134]
        Gene Name: GMPR
        Uniprot ID: P36959 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Ectonucleoside triphosphate diphosphohydrolase 6
        Reactions:
        • a nucleoside diphosphate + H2O = a nucleotide + phosphate [RN:R00329]
        Gene Name: ENTPD6
        Uniprot ID: O75354 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Ectonucleoside triphosphate diphosphohydrolase 5
        Reactions:
        • a nucleoside diphosphate + H2O = a nucleotide + phosphate [RN:R00329]
        Gene Name: ENTPD5
        Uniprot ID: O75356 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylosuccinate synthetase isozyme 2
        Reactions:
        • GTP + IMP + L-aspartate = GDP + phosphate + N6-(1,2-dicarboxyethyl)-AMP [RN:R01135]
        Gene Name: ADSS
        Uniprot ID: P30520 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Inosine-5'-monophosphate dehydrogenase 2
        Reactions:
        • inosine 5'-phosphate + NAD+ + H2O = xanthosine 5'-phosphate + NADH + H+ [RN:R01130]
        Gene Name: IMPDH2
        Uniprot ID: P12268 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Bifunctional purine biosynthesis protein PURH
        Reactions:
        • IMP + H2O = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide [RN:R01127]
        Gene Name: ATIC
        Uniprot ID: P31939 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenylosuccinate synthetase isozyme 1
        Reactions:
        • GTP + IMP + L-aspartate = GDP + phosphate + N6-(1,2-dicarboxyethyl)-AMP [RN:R01135]
        Gene Name: ADSSL1
        Uniprot ID: Q8N142 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytosolic 5'-nucleotidase 3
        Reactions:
        • a 5'-ribonucleotide + H2O = a ribonucleoside + phosphate [RN:R07297]
        Gene Name: NT5C3
        Uniprot ID: Q9H0P0 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: ENTPD4 protein
        Reactions:
          Gene Name: ENTPD4
          Uniprot ID: Q8NE73 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Inosine-5'-monophosphate dehydrogenase
          Reactions:
          • inosine 5'-phosphate + NAD+ + H2O = xanthosine 5'-phosphate + NADH + H+ [RN:R01130]
          Gene Name: IMPDH1
          Uniprot ID: A4D0Z6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Ectonucleoside triphosphate diphosphohydrolase 8
          Reactions:
          • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
          Gene Name: ENTPD8
          Uniprot ID: Q5MY95 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA