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Inosine

Catalog Number
ACM58639-3
CAS
58-63-9
Structure
IUPAC Name
9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
Synonyms
Hypoxanthined-riboside
Molecular Weight
268.23
Molecular Formula
C10H12N4O5
Canonical SMILES
C1=NC2=C(C(=O)N1)N=CN2C3C(C(C(O3)CO)O)O
InChI
InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
InChI Key
UGQMRVRMYYASKQ-KQYNXXCUSA-N
Boiling Point
226 °C
Melting Point
222-226 °C(lit.)
Flash Point
397 °C
Purity
99%
Density
1.3846 g/cm³
Appearance
White crystalline powder
Storage
Keep in dark place, sealed in dry, room temperature
Active Content
95%
Physical State
Solid
Typical Applications
Use as emulsifying agent, dispersing agent.
Use as antistatic agent.
Spec Sheet
Case Study

Inosine Improves Cognitive Function in Aged Female Rats, Reducing Aging-induced Oxidative Stress and Neuroinflammation

Inosine Improves Cognitive Function in Aged Female Rats, Reducing Aging-induced Oxidative Stress and Neuroinflammation Ruhal, Poonam, and Dinesh Dhingra. Inflammopharmacology 26.5 (2018): 1317-1329.

Inosine may significantly improve learning and memory in aged female rats as well as increase the survival rate of hippocampal CA1 neurons in aged rats through its antioxidant and anti-inflammatory actions.
Effects of Inosine on Transfer Latency in Elevated Plus-maze Rats
In the present study, the TL on day 14 did not show any significant changes across all the groups irrespective of the treatment. On day 15 (24 h after the first exposure to elevated plus-maze), the TL was significantly increased in aged rats compared to young rats, indicating a significant memory impairment. Compared to aged control animals, inosine (200 mg/kg) significantly decreased the TL of aged rats on day 15 (retention trial), indicating a significant improvement in memory.
Effects of Inosine on Escape Latency and Time Spent in Target Quadrant in Morris Water Maze Rats
Effects on acquisition (days 11-14): The acquisition data showed that on days 13 and 14 (training days 3 and 4), the EL was significantly increased in aged control animals compared to young control rats, indicating age-induced significant learning deficits. Compared to young rats, inosine (200 mg/kg) and donepezil (1 mg/kg) significantly reduced the EL of aged rats on days 12, 13 and 14 (training days 2, 3 and 4), indicating an improvement in the learning ability of aged rats.
Effects of Inosine on Locomotor Activity in Rats
On the last day of treatment, i.e., day 15, there were no significant differences in the spontaneous locomotor activity across all the treated groups, indicating that inosine did not affect the locomotor activity of rats.
Effects of Inosine on Brain Acetylcholinesterase Activity
The AChE activity in the hippocampus and frontal cortex was significantly reduced in aged control animals compared to young control animals (p<0.001 and 0.001, respectively). Inosine (50, 100 and 200 mg/kg) did not show any significant effect on the AChE activity in aged rats compared to vehicle-treated aged rats.

The Role of Inosine in Biology and Disease

The Role of Inosine in Biology and Disease Srinivasan, Sundaramoorthy, Adrian Gabriel Torres, and Lluís Ribas de Pouplana. Inosine in biology and disease. Genes 12.4 (2021): 600.

Inosine is one of the earliest discovered base modifications in nucleic acids, first identified in 1965 as a constituent of the first sequenced transfer RNA (tRNA), tRNAAla. Inosine is formed by the attachment of the N9 nitrogen of hypoxanthine to the C1 carbon of ribose, creating a purine nucleoside.
The Roles of Inosine in Biology and Disease
Nucleoside inosine plays crucial roles in purine biosynthesis, gene translation, and regulation of RNA fate.
The roles of molecular inosine in metabolism and signaling: Purine nucleotides serve as energy sources, cofactors for metabolic enzymes, and signaling molecules. Thus, molecular inosine is a central intermediate in both purine biosynthesis and degradation pathways, and also plays an important role in neuronal signal transduction.
Inosine in tRNA: The adenosine at position 34 (A34) of tRNA is highly abundant in bacteria and eukaryotes, but absent in archaea. The A34 in tRNA is almost universally modified by tRNA-specific deaminases to inosine (I34). I34 further enhances the wobble pairing flexibility of the anticodon, as I34-tRNAs can recognize A, C or U-ending synonymous codons, in contrast to A34-tRNAs which can only effectively recognize U-ending codons.
Inosine in mRNA: In eukaryotic transcriptomes, A-to-I editing is widespread in non-coding regions. Inosine in 5' and 3' untranslated regions (UTRs) and introns regulates transcript stability, localization and integrity. For example, inosine in 3'UTRs may lead to nuclear retention of mRNAs. This phenomenon was first discovered in mice, where A-to-I editing can control the nuclear retention of 8 kb poly(A)+ RNAs. However, subsequent analyses have reported multiple mRNAs with hyper-edited 3'UTRs that still show cytoplasmic distribution in C. elegans and humans, indicating nuclear retention is not always the result of 3'UTR inosines.

Custom Q&A

What is the molecular formula of inosine?

The molecular formula of inosine is C10H12N4O5.

What is the molecular weight of inosine?

The molecular weight of inosine is 268.23 g/mol.

What is the IUPAC Name of inosine?

The IUPAC Name of inosine is 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one.

What is the InChIKey of inosine?

The InChIKey of inosine is UGQMRVRMYYASKQ-KQYNXXCUSA-N.

What is the Canonical SMILES of inosine?

The Canonical SMILES of inosine is C1=NC2=C(C(=O)N1)N=CN2C3C(C(C(O3)CO)O)O.

What is the CAS number of inosine?

The CAS number of inosine is 58-63-9.

How many hydrogen bond donor counts does inosine have?

Inosine has 4 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does inosine have?

Inosine has 7 hydrogen bond acceptor counts.

What is the XLogP3 value of inosine?

The XLogP3 value of inosine is -1.3.

What is the role of inosine as described in the reference?

Inosine has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, and a mouse metabolite.

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