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| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-02-26 21:21:55 UTC |
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| HMDB ID | HMDB0000175 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Inosinic acid |
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| Description | Inosinic 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. Then, N10-formyltetrahydrofolate (tetrahydrofolate) transfers a formyl group to glycinamide ribonucleotide to form formyl glycinamide ribonucleotide (FGAR). Inosinic acid is a drug. Inosinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). GMP is formed by the inosinate oxidation to xanthylate (XMP), and afterwards adds an amino group on carbon 2. Inosinic acid exists in all living species, ranging from bacteria to humans. Within humans, inosinic acid participates in a number of enzymatic reactions. In particular, inosinic acid can be converted into phosphoribosyl formamidocarboxamide; which is catalyzed by the enzyme bifunctional purine biosynthesis protein purh. In addition, inosinic acid can be converted into xanthylic acid; which is catalyzed by the enzyme inosine-5'-monophosphate dehydrogenase 1. In humans, inosinic acid is involved in the metabolic disorder called the mitochondrial dna depletion syndrome pathway. Inosinic acid is an odorless tasting compound. Outside of the human body, inosinic acid has been detected, but not quantified in, several different foods, such as chinese bayberries, turnips, canada blueberries, oriental wheats, and kiwis. This could make inosinic acid a potential biomarker for the consumption of these foods. These three compounds are used as flavor enhancers for the basic taste umami with a comparatively high effectiveness. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2'-Inosine-5'-monophosphate | ChEBI | | 5'-IMP | ChEBI | | 5'-Inosinate | ChEBI | | 5'-Inosine monophosphate | ChEBI | | 5'-Inosinic acid | ChEBI | | Hypoxanthosine 5'-monophosphate | ChEBI | | Inosine 5'-monophosphate | ChEBI | | Inosine 5'-phosphate | ChEBI | | Inosine monophosphate | ChEBI | | Ribosylhypoxanthine monophosphate | ChEBI | | 2'-Inosine-5'-monophosphoric acid | Generator | | 5'-Inosine monophosphoric acid | Generator | | Hypoxanthosine 5'-monophosphoric acid | Generator | | Inosine 5'-monophosphoric acid | Generator | | Inosine 5'-phosphoric acid | Generator | | Inosine monophosphoric acid | Generator | | Ribosylhypoxanthine monophosphoric acid | Generator | | Inosinate | Generator | | IMP | HMDB | | Inosine-5'-monophosphate | HMDB | | Inosinic acids | HMDB | | Inosinate, sodium | HMDB | | monoPhosphate, inosine | HMDB | | monoPhosphate, ribosylhypoxanthine | HMDB | | Sodium inosinate | HMDB | | Acid, inosinic | HMDB | | Acids, inosinic | HMDB |
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| Chemical Formula | C10H13N4O8P |
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| Average Molecular Weight | 348.206 |
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| Monoisotopic Molecular Weight | 348.047099924 |
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| 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 |
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| Traditional Name | inosine-5'-monophosphate |
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| CAS Registry Number | 131-99-7 |
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| SMILES | O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CNC2=O |
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| 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 |
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| InChI Key | GRSZFWQUAKGDAV-KQYNXXCUSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Nucleosides, nucleotides, and analogues |
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| Class | Purine nucleotides |
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| Sub Class | Purine ribonucleotides |
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| Direct Parent | Purine ribonucleoside monophosphates |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-014i-1952000000-fd534f438bc14efb9a2c | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014i-1952000000-fd534f438bc14efb9a2c | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-0952000000-240bf898db7f932db317 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9703000000-f104482957f10e79ed31 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-01ot-9412200000-ce06d9df7a1b1e9f6bf7 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0900000000-a46a4af4f25c710c773b | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-1900000000-e3960644419fb73668b1 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0fb9-2983200000-58dfb3434545241ee7b6 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-000i-1900000000-d9a723b143b346290896 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9203000000-e2ceede282569ac77de5 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9203000000-e2ceede282569ac77de5 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-1900000000-d9a723b143b346290896 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0914000000-12233517e0b50e335442 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-001099c1a6404d88af4b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01p9-1900000000-3434d7718750395042e3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002k-6709000000-382b74c195ae8ed61127 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002r-8900000000-b96f15a308f90974b444 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-15137ad005d3cad1a603 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Mitochondria
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| Biospecimen Locations | - Blood
- Cellular Cytoplasm
- Cerebrospinal Fluid (CSF)
- Feces
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 63.0 +/- 41.0 uM | Adult (>18 years old) | Both | Normal | | details | | Cellular Cytoplasm | Detected and Quantified | 10 uM | Adult (>18 years old) | Both | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 3.19 (0.00 +/- 19.70) uM | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.31(0.00-41.40) uM | Adult (>18 years old) | Both | Simple febrile seizures | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2.48 (0.00 +/- 27.20) uM | Adult (>18 years old) | Both | Complex febrile seizures | | details | | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Crohns disease | | details | | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Ulcerative colitis | | details | | Feces | Detected but not Quantified | | Children (6 - 18 years old) | Not Specified | Unclassified IBD | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Febrile seizures |
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- 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 |
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- 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 |
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- 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 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | DB04566 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB021901 |
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| KNApSAcK ID | C00007224 |
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| Chemspider ID | 8264 |
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| KEGG Compound ID | C00130 |
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| BioCyc ID | IMP |
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| BiGG ID | 33960 |
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| Wikipedia Link | Inosinic_acid |
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| METLIN ID | 5196 |
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| PubChem Compound | 8582 |
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| PDB ID | Not Available |
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| ChEBI ID | 17202 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| References |
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| 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. |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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