Identification
NameInosinic Acid
Accession NumberDB04566  (EXPT01874)
TypeSmall Molecule
GroupsExperimental
Description

Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.

Structure
Thumb
Synonyms
Cytosine inosinate
External IDs E-630 / INS NO.630 / INS-630
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIITAO7US05G5
CAS number131-99-7
WeightAverage: 348.206
Monoisotopic: 348.047099924
Chemical FormulaC10H13N4O8P
InChI KeyGRSZFWQUAKGDAV-KQYNXXCUSA-N
InChI
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
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
SMILES
O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CNC2=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Glycogen phosphorylase, muscle formProteinunknownNot AvailableHumanP11217 details
Adenylosuccinate synthetaseProteinunknownNot AvailableEscherichia coli (strain K12)P0A7D4 details
Inosine-5'-monophosphate dehydrogenase 2ProteinunknownNot AvailableHumanP12268 details
Adenylosuccinate synthetase isozyme 1ProteinunknownNot AvailableHumanQ8N142 details
Adenylosuccinate synthetaseProteinunknownNot AvailableShigella flexneriQ83P33 details
Inosine-5'-monophosphate dehydrogenaseProteinunknownNot AvailableStreptococcus pyogenesP0C0H6 details
Hypoxanthine phosphoribosyltransferaseProteinunknownNot AvailableEscherichia coli (strain K12)P0A9M2 details
Hypoxanthine-guanine phosphoribosyltransferaseProteinunknownNot AvailableTrypanosoma cruziQ27796 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

Yasuhiko Yoshihara, Yoshio Kawahara, Yasutsugu Yamada, Sigeho Ikeda, "Process for producing 5'-inosinic acid by fermentation." U.S. Patent US5164306, issued September, 1985.

US5164306
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
pKa2.4MERCK INDEX (1996); pK1
Predicted Properties
PropertyValueSource
Water Solubility3.05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.2 m3·mol-1ChemAxon
Polarizability29.14 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6465
Blood Brain Barrier+0.8446
Caco-2 permeable-0.7846
P-glycoprotein substrateNon-substrate0.6408
P-glycoprotein inhibitor INon-inhibitor0.9088
P-glycoprotein inhibitor IINon-inhibitor0.9537
Renal organic cation transporterNon-inhibitor0.9512
CYP450 2C9 substrateNon-substrate0.7918
CYP450 2D6 substrateNon-substrate0.8409
CYP450 3A4 substrateNon-substrate0.5361
CYP450 1A2 substrateNon-inhibitor0.8701
CYP450 2C9 inhibitorNon-inhibitor0.9332
CYP450 2D6 inhibitorNon-inhibitor0.8969
CYP450 2C19 inhibitorNon-inhibitor0.9266
CYP450 3A4 inhibitorNon-inhibitor0.9471
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9654
Ames testNon AMES toxic0.9292
CarcinogenicityNon-carcinogens0.9094
BiodegradationNot ready biodegradable0.7728
Rat acute toxicity1.9834 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9629
hERG inhibition (predictor II)Non-inhibitor0.8388
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-014i-1952000000-fd534f438bc14efb9a2cView 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative ParentsPentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Pyrimidones / Monoalkyl phosphates / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds
SubstituentsPurine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Pentose monosaccharide / Imidazopyrimidine
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorspurine ribonucleoside 5'-monophosphate, inosine phosphate (CHEBI:17202 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Pyridoxal phosphate binding
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:
97091.265 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Magnesium ion binding
Specific Function:
Plays an important role in the de novo pathway of purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
Gene Name:
purA
Uniprot ID:
P0A7D4
Molecular Weight:
47344.585 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Rna binding
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 t...
Gene Name:
IMPDH2
Uniprot ID:
P12268
Molecular Weight:
55804.495 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Phosphate ion binding
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 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Shigella flexneri
Pharmacological action
unknown
General Function:
Magnesium ion binding
Specific Function:
Plays an important role in the de novo pathway of purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
Gene Name:
purA
Uniprot ID:
Q83P33
Molecular Weight:
47314.555 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Streptococcus pyogenes
Pharmacological action
unknown
General Function:
Metal ion binding
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.
Gene Name:
guaB
Uniprot ID:
P0C0H6
Molecular Weight:
52806.77 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Nucleotide binding
Specific Function:
Acts preferentially on hypoxanthine; has very low activity towards guanine. Inactive towards xanthine.
Gene Name:
hpt
Uniprot ID:
P0A9M2
Molecular Weight:
20115.025 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Trypanosoma cruzi
Pharmacological action
unknown
General Function:
Hypoxanthine phosphoribosyltransferase activity
Specific Function:
Not Available
Gene Name:
HGPRTase
Uniprot ID:
Q27796
Molecular Weight:
25529.02 Da
Drug created on June 13, 2005 07:24 / Updated on June 23, 2017 10:18