Inosinic Acid

Identification

Name
Inosinic Acid
Accession Number
DB04566  (EXPT01874)
Type
Small Molecule
Groups
Experimental
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
Categories
UNII
TAO7US05G5
CAS number
131-99-7
Weight
Average: 348.206
Monoisotopic: 348.047099924
Chemical Formula
C10H13N4O8P
InChI Key
GRSZFWQUAKGDAV-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[[email protected]@H]1[[email protected]@H](COP(O)(O)=O)O[[email protected]]([[email protected]@H]1O)N1C=NC2=C1N=CNC2=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlycogen phosphorylase, muscle formNot AvailableHuman
UAdenylosuccinate synthetaseNot AvailableEscherichia coli (strain K12)
UInosine-5'-monophosphate dehydrogenase 2Not AvailableHuman
UAdenylosuccinate synthetase isozyme 1Not AvailableHuman
UAdenylosuccinate synthetaseNot AvailableShigella flexneri
UInosine-5'-monophosphate dehydrogenaseNot AvailableStreptococcus pyogenes
UHypoxanthine phosphoribosyltransferaseNot AvailableEscherichia coli (strain K12)
UHypoxanthine-guanine phosphoribosyltransferaseNot AvailableTrypanosoma cruzi
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00175
KEGG Compound
C00130
PubChem Compound
8582
PubChem Substance
46504691
ChemSpider
8264
BindingDB
19254
ChEBI
17202
ChEMBL
CHEMBL1207374
HET
IMP
PDB Entries
1abb / 1b4d / 1ce8 / 1ch8 / 1cib / 1ftq / 1g9s / 1gfz / 1gg8 / 1gim
show 97 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-014i-1952000000-fd534f438bc14efb9a2c
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-1952000000-fd534f438bc14efb9a2c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-014i-0952000000-240bf898db7f932db317
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0900000000-a46a4af4f25c710c773b
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-000i-1900000000-e3960644419fb73668b1
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0fb9-2983200000-58dfb3434545241ee7b6
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-000i-1900000000-d9a723b143b346290896
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-002b-9203000000-e2ceede282569ac77de5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-002b-9203000000-e2ceede282569ac77de5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-1900000000-d9a723b143b346290896
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Pyrimidones / Monoalkyl phosphates / N-substituted imidazoles / Heteroaromatic compounds / Tetrahydrofurans
show 10 more
Substituents
Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Pentose monosaccharide / Imidazopyrimidine
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
purine 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 ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
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
Uniprot Name
Adenylosuccinate synthetase
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 pl...
Gene Name
IMPDH2
Uniprot ID
P12268
Uniprot Name
Inosine-5'-monophosphate dehydrogenase 2
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. Catalyz...
Gene Name
ADSSL1
Uniprot ID
Q8N142
Uniprot Name
Adenylosuccinate synthetase isozyme 1
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
Uniprot Name
Adenylosuccinate synthetase
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 pl...
Gene Name
guaB
Uniprot ID
P0C0H6
Uniprot Name
Inosine-5'-monophosphate dehydrogenase
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
Uniprot Name
Hypoxanthine phosphoribosyltransferase
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
Uniprot Name
Hypoxanthine-guanine phosphoribosyltransferase
Molecular Weight
25529.02 Da

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:43