Record Information
Version1.0
Created at2020-04-17 18:39:30 UTC
Updated at2020-12-07 19:11:00 UTC
CannabisDB IDCDB004814
Secondary Accession NumbersNot Available
Cannabis Compound 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 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 through the action of the enzyme bifunctional purine biosynthesis protein purh. In addition, inosinic acid can be converted into xanthylic acid through its interaction with the enzyme inosine-5'-monophosphate dehydrogenase 1. In humans, inosinic acid is involved in the metabolic disorder called the gout or kelley-seegmiller 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 hickory nuts, turnips, pepper (spice), mountain yams, and muskmelons. This could make inosinic acid a potential biomarker for the consumption of these foods. A purine ribonucleoside 5'-monophosphate having hypoxanthine as the nucleobase. Inosinic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight348.21
Monoisotopic Molecular Weight348.0471
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSInosinic acid, 5 TMS, GC-MS Spectrumsplash10-014i-1952000000-fd534f438bc14efb9a2cSpectrum
GC-MSInosinic acid, non-derivatized, GC-MS Spectrumsplash10-014i-1952000000-fd534f438bc14efb9a2cSpectrum
GC-MSInosinic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0952000000-240bf898db7f932db317Spectrum
Predicted GC-MSInosinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9703000000-f104482957f10e79ed31Spectrum
Predicted GC-MSInosinic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-9412200000-ce06d9df7a1b1e9f6bf7Spectrum
Predicted GC-MSInosinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSInosinic acid, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-a46a4af4f25c710c773bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-1900000000-e3960644419fb73668b1Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fb9-2983200000-58dfb3434545241ee7b6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-1900000000-d9a723b143b346290896Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9203000000-e2ceede282569ac77de5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9203000000-e2ceede282569ac77de5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-1900000000-d9a723b143b346290896Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-2009000000-fd4ac18ae0dd374e6ff5Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004j-9201000000-349e076b55d7b34813f1Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-7d260970c5fd63733d68Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-29a9853c167178a536caSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-d15c645092c15796fecfSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-1920000000-cce3d9b2f5486a013f43Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-123dc62f6eec7f2a443aSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-74854877c4d899dd1cbfSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-1910000000-92a97d045ff5a88d7fefSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-780ab0f4378101c42e44Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-ccbd03a9087207ab2a25Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-69d1aff415931bcc4325Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0914000000-12233517e0b50e335442Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-001099c1a6404d88af4bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-3434d7718750395042e3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002k-6709000000-382b74c195ae8ed61127Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-8900000000-b96f15a308f90974b444Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-15137ad005d3cad1a603Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Ectonucleoside triphosphate diphosphohydrolase 1ENTPD110q24P49961 details
Soluble calcium-activated nucleotidase 1CANT117q25.3Q8WVQ1 details
Ectonucleoside triphosphate diphosphohydrolase 3ENTPD33p21.3O75355 details
Glycogen phosphorylase, liver formPYGL14q21-q22P06737 details
Glycogen phosphorylase, muscle formPYGM11q12-q13.2P11217 details
Glycogen phosphorylase, brain formPYGB20p11.21P11216 details
Inosine triphosphate pyrophosphataseITPA20pQ9BY32 details
Hypoxanthine-guanine phosphoribosyltransferaseHPRT1Xq26.1P00492 details
AMP deaminase 3AMPD311p15Q01432 details
AMP deaminase 2AMPD21p13.3Q01433 details
AMP deaminase 1AMPD11p13P23109 details
GMP reductase 2GMPR214q12Q9P2T1 details
GMP reductase 1GMPR6p23P36959 details
Ectonucleoside triphosphate diphosphohydrolase 4ENTPD48p21.3Q9Y227 details
Ectonucleoside triphosphate diphosphohydrolase 6ENTPD620p11.21O75354 details
Ectonucleoside triphosphate diphosphohydrolase 5ENTPD514q24O75356 details
Adenylosuccinate synthetase isozyme 2ADSS1q44P30520 details
Inosine-5'-monophosphate dehydrogenase 2IMPDH23p21.2P12268 details
Bifunctional purine biosynthesis protein PURHATIC2q35P31939 details
Inosine-5'-monophosphate dehydrogenase 1IMPDH17q31.3-q32P20839 details
Adenylosuccinate synthetase isozyme 1ADSSL114q32.33Q8N142 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
ENTPD4 proteinENTPD48p21.3Q8NE73 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
Inosine-5'-monophosphate dehydrogenaseIMPDH17q31.3-q32A4D0Z6 details
Ectonucleoside triphosphate diphosphohydrolase 8ENTPD89q34.3Q5MY95 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Soluble calcium-activated nucleotidase 1CANT117q25.3Q8WVQ1 details
Inosine triphosphate pyrophosphataseITPA20pQ9BY32 details
AMP deaminase 3AMPD311p15Q01432 details
AMP deaminase 2AMPD21p13.3Q01433 details
AMP deaminase 1AMPD11p13P23109 details
GMP reductase 2GMPR214q12Q9P2T1 details
GMP reductase 1GMPR6p23P36959 details
Adenylosuccinate synthetase isozyme 2ADSS1q44P30520 details
Inosine-5'-monophosphate dehydrogenase 2IMPDH23p21.2P12268 details
Inosine-5'-monophosphate dehydrogenase 1IMPDH17q31.3-q32P20839 details
Adenylosuccinate synthetase isozyme 1ADSSL114q32.33Q8N142 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000175
DrugBank IDDB04566
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 IDNot Available
ChEBI ID17202
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 49 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
General function:
Involved in hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
General function:
Involved in hydrolase activity
Specific function:
Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:
ENTPD3
Uniprot ID:
O75355
Molecular weight:
59104.76
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
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:
PYGM
Uniprot ID:
P11217
Molecular weight:
87316.355

Only showing the first 10 proteins. There are 49 proteins in total.