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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 18:58:07 UTC
HMDB IDHMDB0000175
Secondary Accession Numbers
  • HMDB00175
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
ValueSource
2'-Inosine-5'-monophosphateChEBI
5'-IMPChEBI
5'-InosinateChEBI
5'-Inosine monophosphateChEBI
5'-Inosinic acidChEBI
Hypoxanthosine 5'-monophosphateChEBI
Inosine 5'-monophosphateChEBI
Inosine 5'-phosphateChEBI
Inosine monophosphateChEBI
Ribosylhypoxanthine monophosphateChEBI
2'-Inosine-5'-monophosphoric acidGenerator
InosinateGenerator
5'-Inosine monophosphoric acidGenerator
Hypoxanthosine 5'-monophosphoric acidGenerator
Inosine 5'-monophosphoric acidGenerator
Inosine 5'-phosphoric acidGenerator
Inosine monophosphoric acidGenerator
Ribosylhypoxanthine monophosphoric acidGenerator
IMPHMDB
Inosine-5'-monophosphateHMDB
Inosinic acidsMeSH
Inosinate, sodiumMeSH
Monophosphate, inosineMeSH
Monophosphate, ribosylhypoxanthineMeSH
Sodium inosinateMeSH
Acid, inosinicMeSH
Acids, inosinicMeSH
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 Nameinosine-5'-monophosphate
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
DescriptionThis compound 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 Area175.73 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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-014i-1952000000-fd534f438bc14efb9a2cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1952000000-fd534f438bc14efb9a2cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0952000000-240bf898db7f932db317View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9703000000-f104482957f10e79ed31View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9412200000-ce06d9df7a1b1e9f6bf7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-a46a4af4f25c710c773bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-e3960644419fb73668b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-2983200000-58dfb3434545241ee7b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-1900000000-d9a723b143b346290896View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9203000000-e2ceede282569ac77de5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9203000000-e2ceede282569ac77de5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-1900000000-d9a723b143b346290896View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0914000000-12233517e0b50e335442View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-001099c1a6404d88af4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-3434d7718750395042e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002k-6709000000-382b74c195ae8ed61127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-8900000000-b96f15a308f90974b444View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-15137ad005d3cad1a603View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified63.0 +/- 41.0 uMAdult (>18 years old)BothNormal details
Cellular CytoplasmDetected and Quantified10 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.19 (0.00 +/- 19.70) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified2.31(0.00-41.40) uMAdult (>18 years old)BothSimple febrile seizures details
Cerebrospinal Fluid (CSF)Detected and Quantified2.48 (0.00 +/- 27.20) uMAdult (>18 years old)BothComplex febrile seizures details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedCrohns disease details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUlcerative colitis details
FecesDetected but not Quantified Children (6 - 18 years old)Not SpecifiedUnclassified IBD details
Associated Disorders and Diseases
Disease References
Febrile seizures
  1. 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 ]
Crohn's disease
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
  1. Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021901
KNApSAcK IDC00007224
Chemspider ID8264
KEGG Compound IDC00130
BioCyc IDIMP
BiGG ID33960
Wikipedia LinkInosinic_acid
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)Download (PDF)
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;2:18. [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 (1985). 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 (1985). 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 (1985). 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 ]

Only showing the first 10 proteins. There are 31 proteins in total.

Enzymes

General function:
Involved in deaminase activity
Specific function:
AMP deaminase plays a critical role in energy metabolism.
Gene Name:
AMPD1
Uniprot ID:
P23109
Molecular weight:
90218.455
Reactions
Adenosine monophosphate + Water → Inosinic acid + Ammoniadetails
General function:
Involved in adenylosuccinate synthase activity
Specific function:
Component of the purine nucleotide cycle (PNC), which interconverts IMP and AMP to regulate the nucleotide levels in various tissues, and which contributes to glycolysis and ammoniagenesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP (By similarity).
Gene Name:
ADSSL1
Uniprot ID:
Q8N142
Molecular weight:
50208.16
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Phosphoric acid + N(6)-(1,2-dicarboxyethyl)AMPdetails
General function:
Involved in IMP cyclohydrolase activity
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
P31939
Molecular weight:
64615.255
Reactions
Inosinic acid + Water → Phosphoribosyl formamidocarboxamidedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the irreversible NADPH-dependent deamination of GMP to IMP. It functions in the conversion of nucleobase, nucleoside and nucleotide derivatives of G to A nucleotides, and in maintaining the intracellular balance of A and G nucleotides.
Gene Name:
GMPR
Uniprot ID:
P36959
Molecular weight:
37418.58
Reactions
Inosinic acid + Ammonia + NADP → Guanosine monophosphate + NADPHdetails
Inosinic acid + Ammonia + NADP → Guanosine monophosphate + NADPH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
Inosine 5'-phosphate + NAD(+) + H(2)O = xanthosine 5'-phosphate + NADH
Gene Name:
IMPDH1
Uniprot ID:
A4D0Z6
Molecular weight:
64319.3
General function:
Involved in hypoxanthine phosphoribosyltransferase activity
Specific function:
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
Gene Name:
HPRT1
Uniprot ID:
P00492
Molecular weight:
24579.155
Reactions
Inosinic acid + Pyrophosphate → Hypoxanthine + Phosphoribosyl pyrophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of inosine 5'-phosphate (IMP) to xanthosine 5'-phosphate (XMP), the first committed and rate-limiting step in the de novo synthesis of guanine nucleotides, and therefore plays an important role in the regulation of cell growth. Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism. It may also have a role in the development of malignancy and the growth progression of some tumors.
Gene Name:
IMPDH2
Uniprot ID:
P12268
Molecular weight:
55804.495
Reactions
Inosinic acid + NAD + Water → Xanthylic acid + NADHdetails
Inosinic acid + NAD + Water → Xanthylic acid + NADH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the irreversible NADPH-dependent deamination of GMP to IMP. It functions in the conversion of nucleobase, nucleoside and nucleotide derivatives of G to A nucleotides, and in maintaining the intracellular balance of A and G nucleotides. Plays a role in modulating cellular differentiation.
Gene Name:
GMPR2
Uniprot ID:
Q9P2T1
Molecular weight:
37874.125
Reactions
Inosinic acid + Ammonia + NADP → Guanosine monophosphate + NADPHdetails
Inosinic acid + Ammonia + NADP → Guanosine monophosphate + NADPH + Hydrogen Iondetails
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGB
Uniprot ID:
P11216
Molecular weight:
96695.18
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25

Only showing the first 10 proteins. There are 31 proteins in total.