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Record Information
Version1.0
Creation Date2016-09-30 22:20:32 UTC
Update Date2020-06-04 20:56:16 UTC
BMDB IDBMDB0000175
Secondary Accession Numbers
  • BMDB00175
Metabolite Identification
Common NameInosinic acid
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 possibly soluble (in water) and 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
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
5'-Inosine monophosphoric acidGenerator
Hypoxanthosine 5'-monophosphoric acidGenerator
Inosine 5'-monophosphoric acidGenerator
Inosine 5'-phosphoric acidGenerator
Inosine monophosphoric acidGenerator
Ribosylhypoxanthine monophosphoric acidGenerator
InosinateGenerator
IMPHMDB
Inosine-5'-monophosphateHMDB
Inosinic acidsHMDB
Inosinate, sodiumHMDB
monoPhosphate, inosineHMDB
monoPhosphate, ribosylhypoxanthineHMDB
Sodium inosinateHMDB
Acid, inosinicHMDB
Acids, inosinicHMDB
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
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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • 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
logP-2ALOGPS
logP-2.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.31ChemAxon
pKa (Strongest Basic)0.49ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
  • Mitochondria
Biospecimen Locations
  • All Tissues
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Muscle
  • Semimembranosus Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified34 +/- 27 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Longissimus Thoracis MuscleDetected and Quantified15 +/- 11 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MuscleDetected and Quantified40-8977 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified460 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified31-59 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Semimembranosus MuscleDetected and Quantified124 +/- 136 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified97 +/- 19 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000175
DrugBank IDDB04566
Phenol Explorer Compound IDNot Available
FooDB IDFDB021901
KNApSAcK IDC00007224
Chemspider ID8264
KEGG Compound IDC00130
BioCyc IDIMP
BiGG ID33960
Wikipedia LinkInosinic_acid
METLIN ID5196
PubChem Compound8582
PDB IDNot Available
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. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]

Enzymes

General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
O46411
Molecular weight:
64841.0
Reactions
Inosinic acid + Water → Inosine + Hydrogen phosphatedetails
General function:
Not Available
Specific function:
Canalicular ectonucleoside NTPDase responsible for the main hepatic NTPDase activity. Ectonucleoside NTPDases catalyze the hydrolysis of gamma- and beta-phosphate residues of nucleotides, playing a central role in concentration of extracellular nucleotides. Has activity toward ATP, ADP, UTP and UDP, but not toward AMP (By similarity).
Gene Name:
ENTPD8
Uniprot ID:
A0JND9
Molecular weight:
53240.0
Reactions
IDP + Water → Inosinic acid + Hydrogen phosphatedetails
General function:
Nucleotide transport and metabolism
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 (Probable). Plays a role in modulating cellular differentiation (By similarity).
Gene Name:
GMPR2
Uniprot ID:
Q32L93
Molecular weight:
38033.0
Reactions
Inosinic acid + Ammonia + NADP → Guanosine monophosphate + NADPHdetails
General function:
Nucleotide transport and metabolism
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 (By similarity).
Gene Name:
HPRT1
Uniprot ID:
Q3SZ18
Molecular weight:
24498.0
Reactions
Inosinic acid + Pyrophosphate → Hypoxanthine + Phosphoribosyl pyrophosphatedetails
General function:
Nucleotide transport and metabolism
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.
Gene Name:
ADSS1
Uniprot ID:
A5PJR4
Molecular weight:
50134.0
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Hydrogen phosphate + Adenylsuccinic aciddetails
General function:
Nucleotide transport and metabolism
Specific function:
Pyrophosphatase that hydrolyzes the non-canonical purine nucleotides inosine triphosphate (ITP), deoxyinosine triphosphate (dITP) as well as 2'-deoxy-N-6-hydroxylaminopurine triposphate (dHAPTP) and xanthosine 5'-triphosphate (XTP) to their respective monophosphate derivatives. The enzyme does not distinguish between the deoxy- and ribose forms. Probably excludes non-canonical purines from RNA and DNA precursor pools, thus preventing their incorporation into RNA and DNA and avoiding chromosomal lesions.
Gene Name:
ITPA
Uniprot ID:
Q2KIC5
Molecular weight:
23061.0
Reactions
Inosine triphosphate + Water → Inosinic acid + Pyrophosphatedetails
General function:
Nucleotide transport and metabolism
Specific function:
Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
Gene Name:
ADSS2
Uniprot ID:
A7MBG0
Molecular weight:
50156.0
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Hydrogen phosphate + Adenylsuccinic aciddetails
General function:
Nucleotide transport and metabolism
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
Q0VCK0
Molecular weight:
64483.0
Reactions
Inosinic acid + Water → Phosphoribosyl formamidocarboxamidedetails
General function:
Nucleotide transport and metabolism
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:
Q08DA2
Molecular weight:
37504.0
General function:
Nucleotide transport and metabolism
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:
Q3SWY3
Molecular weight:
55763.0
General function:
Nucleotide transport and metabolism
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:
IMPDH1
Uniprot ID:
A0JNA3
Molecular weight:
55424.0
Reactions
Inosinic acid + NAD + Water → Xanthylic acid + NADHdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
AMPD3
Uniprot ID:
E1BA23
Molecular weight:
52079.0
Reactions
Adenosine monophosphate + Water → Inosinic acid + Ammoniadetails