Inosinic Acid
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Identification
- Generic Name
- Inosinic Acid
- DrugBank Accession Number
- DB04566
- Background
Inosine 5'-Monophosphate. A purine nucleotide which has hypoxanthine as the base and one phosphate group esterified to the sugar moiety.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 348.206
Monoisotopic: 348.047099924 - Chemical Formula
- C10H13N4O8P
- Synonyms
- Cytosine inosinate
- External IDs
- E-630
- INS NO.630
- INS-630
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AInosine-5'-monophosphate dehydrogenase 1 inhibitorHumans AHypoxanthine-guanine-xanthine phosphoribosyltransferase inhibitorPlasmodium falciparum (isolate FCR-3 / Gambia) AAdenylosuccinate synthetase inhibitorPlasmodium falciparum AInosine-5'-monophosphate dehydrogenase 2 inhibitorHumans AGlycogen phosphorylase, muscle form inhibitorHumans UAdenylosuccinate synthetase Not Available Escherichia coli (strain K12) UAdenylosuccinate synthetase isozyme 1 Not Available Humans UAdenylosuccinate synthetase Not Available Shigella flexneri UInosine-5'-monophosphate dehydrogenase Not Available Streptococcus pyogenes UHypoxanthine phosphoribosyltransferase Not Available Escherichia coli (strain K12) UHypoxanthine-guanine phosphoribosyltransferase Not Available Trypanosoma 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-diol / 6-oxopurine / Alcohol / Alkyl phosphate / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative show 29 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- purine ribonucleoside 5'-monophosphate, inosine phosphate (CHEBI:17202)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- TAO7US05G5
- CAS number
- 131-99-7
- 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[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CNC2=O
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
- HMDB0000175
- KEGG Compound
- C00130
- PubChem Compound
- 8582
- PubChem Substance
- 46504691
- ChemSpider
- 8264
- BindingDB
- 19254
- 5832
- ChEBI
- 17202
- ChEMBL
- CHEMBL1207374
- ZINC
- ZINC000004228242
- PDBe Ligand
- IMP
- Wikipedia
- Inosinic_acid
- PDB Entries
- 1abb / 1b4d / 1ce8 / 1ch8 / 1cib / 1ftq / 1g9s / 1gfz / 1gg8 / 1gim … show 170 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data0 Completed Treatment Anatomic Stage IV Breast Cancer AJCC / Estrogen Receptor Negative / HER2 negative / Progesterone Receptor Negative / Triple-Negative Breast Cancer 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source pKa 2.4 MERCK INDEX (1996); pK1 - Predicted Properties
Property Value Source Water Solubility 3.05 mg/mL ALOGPS logP -2 ALOGPS logP -2.9 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 1.31 Chemaxon pKa (Strongest Basic) 0.49 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 175.73 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 72.2 m3·mol-1 Chemaxon Polarizability 29.14 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6465 Blood Brain Barrier + 0.8446 Caco-2 permeable - 0.7846 P-glycoprotein substrate Non-substrate 0.6408 P-glycoprotein inhibitor I Non-inhibitor 0.9088 P-glycoprotein inhibitor II Non-inhibitor 0.9537 Renal organic cation transporter Non-inhibitor 0.9512 CYP450 2C9 substrate Non-substrate 0.7918 CYP450 2D6 substrate Non-substrate 0.8409 CYP450 3A4 substrate Non-substrate 0.5361 CYP450 1A2 substrate Non-inhibitor 0.8701 CYP450 2C9 inhibitor Non-inhibitor 0.9332 CYP450 2D6 inhibitor Non-inhibitor 0.8969 CYP450 2C19 inhibitor Non-inhibitor 0.9266 CYP450 3A4 inhibitor Non-inhibitor 0.9471 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9654 Ames test Non AMES toxic 0.9292 Carcinogenicity Non-carcinogens 0.9094 Biodegradation Not ready biodegradable 0.7728 Rat acute toxicity 1.9834 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9629 hERG inhibition (predictor II) Non-inhibitor 0.8388
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 189.7687459 predictedDarkChem Lite v0.1.0 [M-H]- 187.5482459 predictedDarkChem Lite v0.1.0 [M-H]- 189.6773459 predictedDarkChem Lite v0.1.0 [M-H]- 156.66028 predictedDeepCCS 1.0 (2019) [M+H]+ 189.2598459 predictedDarkChem Lite v0.1.0 [M+H]+ 187.6017459 predictedDarkChem Lite v0.1.0 [M+H]+ 188.6133459 predictedDarkChem Lite v0.1.0 [M+H]+ 159.05586 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.4716459 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.2898459 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.0423459 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.22157 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsInosine-5'-monophosphate dehydrogenase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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
- Specific Function
- DNA binding
- Gene Name
- IMPDH1
- Uniprot ID
- P20839
- Uniprot Name
- Inosine-5'-monophosphate dehydrogenase 1
- Molecular Weight
- 55405.365 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Plasmodium falciparum (isolate FCR-3 / Gambia)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the transfer of a ribosyl phosphate group from 5-phosphoribose 1-diphosphate to the N(9) of hypoxanthine, guanine or xanthine, leading to IMP, GMP and XMP, respectively. Plays a central role in the generation of purine nucleotides through the purine salvage pathway.
- Specific Function
- guanine phosphoribosyltransferase activity
- Gene Name
- LACZ
- Uniprot ID
- P20035
- Uniprot Name
- Hypoxanthine-guanine-xanthine phosphoribosyltransferase
- Molecular Weight
- 26348.18 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsAdenylosuccinate synthetase
- Kind
- Protein
- Organism
- Plasmodium falciparum
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Plays an important role in the salvage pathway for purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP (By similarity).
- Specific Function
- adenylosuccinate synthase activity
- Gene Name
- Adss
- Uniprot ID
- Q9U8D3
- Uniprot Name
- Adenylosuccinate synthetase
- Molecular Weight
- 50064.525 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
4. DetailsInosine-5'-monophosphate dehydrogenase 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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 (PubMed:7763314, PubMed:7903306). Could also have a single-stranded nucleic acid-binding activity and could play a role in RNA and/or DNA metabolism (PubMed:14766016). It may also have a role in the development of malignancy and the growth progression of some tumors
- Specific Function
- DNA binding
- Gene Name
- IMPDH2
- Uniprot ID
- P12268
- Uniprot Name
- Inosine-5'-monophosphate dehydrogenase 2
- Molecular Weight
- 55804.495 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
5. DetailsGlycogen phosphorylase, muscle form
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Allosteric enzyme that catalyzes the rate-limiting step in glycogen catabolism, the phosphorolytic cleavage of glycogen to produce glucose-1-phosphate, and plays a central role in maintaining cellular and organismal glucose homeostasis
- Specific Function
- glycogen phosphorylase activity
- Gene Name
- PYGM
- Uniprot ID
- P11217
- Uniprot Name
- Glycogen phosphorylase, muscle form
- Molecular Weight
- 97091.265 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
6. DetailsAdenylosuccinate synthetase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General 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.
- Specific Function
- adenylosuccinate synthase activity
- Gene Name
- purA
- Uniprot ID
- P0A7D4
- Uniprot Name
- Adenylosuccinate synthetase
- Molecular Weight
- 47344.585 Da
References
7. DetailsAdenylosuccinate synthetase isozyme 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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
- Specific Function
- actin filament binding
- Gene Name
- ADSS1
- Uniprot ID
- Q8N142
- Uniprot Name
- Adenylosuccinate synthetase isozyme 1
- Molecular Weight
- 50208.16 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
8. DetailsAdenylosuccinate synthetase
- Kind
- Protein
- Organism
- Shigella flexneri
- Pharmacological action
- Unknown
- General 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.
- Specific Function
- adenylosuccinate synthase activity
- Gene Name
- purA
- Uniprot ID
- Q83P33
- Uniprot Name
- Adenylosuccinate synthetase
- Molecular Weight
- 47314.555 Da
References
9. DetailsInosine-5'-monophosphate dehydrogenase
- Kind
- Protein
- Organism
- Streptococcus pyogenes
- Pharmacological action
- Unknown
- General 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.
- Specific Function
- IMP dehydrogenase activity
- Gene Name
- guaB
- Uniprot ID
- P0C0H6
- Uniprot Name
- Inosine-5'-monophosphate dehydrogenase
- Molecular Weight
- 52806.77 Da
References
10. DetailsHypoxanthine phosphoribosyltransferase
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Purine salvage pathway enzyme which catalyzes the transfer of the ribosyl-5-phosphate group from 5-phospho-alpha-D-ribose 1-diphosphate (PRPP) to the N9 position of hypoxanthine to yield IMP (inosine 5'-monophosphate). To a lesser extent, can also act on guanine leading to GMP, but shows a highly less efficient activity with xanthine.
- Specific Function
- guanine phosphoribosyltransferase activity
- Gene Name
- hpt
- Uniprot ID
- P0A9M2
- Uniprot Name
- Hypoxanthine phosphoribosyltransferase
- Molecular Weight
- 20115.025 Da
References
- Kind
- Protein
- Organism
- Trypanosoma cruzi
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- guanine phosphoribosyltransferase activity
- Gene Name
- HGPRTase
- Uniprot ID
- Q27796
- Uniprot Name
- Hypoxanthine-guanine phosphoribosyltransferase
- Molecular Weight
- 25529.02 Da
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22