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 UGlycogen phosphorylase, muscle form Not Available Humans UAdenylosuccinate synthetase Not Available Escherichia coli (strain K12) UInosine-5'-monophosphate dehydrogenase 2 Not Available Humans 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 164 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 0 Completed Treatment Anatomic Stage IV Breast Cancer AJCC / Estrogen Receptor Negative / HER2 negative / Progesterone Receptor Negative / Triple-Negative Breast Cancer 1
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. DetailsGlycogen phosphorylase, muscle form
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
2. DetailsAdenylosuccinate synthetase
- 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
3. DetailsInosine-5'-monophosphate dehydrogenase 2
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
4. DetailsAdenylosuccinate synthetase isozyme 1
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
5. DetailsAdenylosuccinate synthetase
- 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
6. DetailsInosine-5'-monophosphate dehydrogenase
- 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
7. DetailsHypoxanthine phosphoribosyltransferase
- 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
- 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 at June 13, 2005 13:24 / Updated at June 12, 2020 16:52