Record Information |
---|
Version | 1.0 |
---|
Created at | 2020-04-17 18:39:55 UTC |
---|
Updated at | 2020-12-07 19:11:01 UTC |
---|
CannabisDB ID | CDB004818 |
---|
Secondary Accession Numbers | Not Available |
---|
Cannabis Compound Identification |
---|
Common Name | Inosine |
---|
Description | Inosine, also known as hypoxanthosine or inotin, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. A purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. Inosine is a moderately basic compound (based on its pKa). Inosine exists in all living species, ranging from bacteria to humans. Within humans, inosine participates in a number of enzymatic reactions. In particular, inosine can be biosynthesized from inosinic acid through its interaction with the enzyme cytosolic purine 5'-nucleotidase. In addition, inosine can be converted into hypoxanthine and ribose 1-phosphate through its interaction with the enzyme purine nucleoside phosphorylase. In humans, inosine is involved in the metabolic disorder called the gout or kelley-seegmiller syndrome pathway. Inosine is a potentially toxic compound. Inosine, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, degenerative disc disease, kidney disease, and gout; inosine has also been linked to the inborn metabolic disorder xanthinuria type 1. Inosine is expected to be in Cannabis as all living plants are known to produce and metabolize it. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
9-beta-D-Ribofuranosyl-9H-purin-6-ol | ChEBI | 9-beta-D-Ribofuranosylhypoxanthine | ChEBI | Hypoxanthine D-riboside | ChEBI | Hypoxanthosine | ChEBI | i | ChEBI | Inosin | ChEBI | Inosina | ChEBI | Inosinum | ChEBI | Inotin | Kegg | 9-b-D-Ribofuranosyl-9H-purin-6-ol | Generator | 9-Β-D-ribofuranosyl-9H-purin-6-ol | Generator | 9-b-D-Ribofuranosylhypoxanthine | Generator | 9-Β-D-ribofuranosylhypoxanthine | Generator | (-)-Inosine | HMDB | 1,9-Dihydro-9-b-D-ribofuranosyl-6H-purin-6-one | HMDB | 1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one | HMDB | 1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one | HMDB | 9-b-D-Ribofuranosyl-hypoxanthine | HMDB | 9-beta-D-Ribofuranosyl-hypoxanthine | HMDB | 9-beta-delta-Ribofuranosyl-hypoxanthine | HMDB | 9-beta-delta-Ribofuranosylhypoxanthine | HMDB | 9beta-D-Ribofuranosylhypoxanthine | HMDB | 9beta-delta-Ribofuranosylhypoxanthine | HMDB | Atorel | HMDB | beta-D-Ribofuranoside hypoxanthine-9 | HMDB | beta-delta-Ribofuranoside hypoxanthine-9 | HMDB | beta-Inosine | HMDB | HXR | HMDB | Hypoxanthine 9-beta-D-ribofuranoside | HMDB | Hypoxanthine 9-beta-delta-ribofuranoside | HMDB | Hypoxanthine nucleoside | HMDB | Hypoxanthine ribonucleoside | HMDB | Hypoxanthine riboside | HMDB | Hypoxanthine-9 beta-D-ribofuranoside | HMDB | Hypoxanthine-9 beta-delta-ribofuranoside | HMDB | Hypoxanthine-9-beta-D-ribofuranoside | HMDB | Hypoxanthine-9-beta-delta-ribofuranoside | HMDB | Hypoxanthine-9-D-ribofuranoside | HMDB | Hypoxanthine-9-delta-ribofuranoside | HMDB | Hypoxanthine-ribose | HMDB | Indole-3-carboxaldehyde | HMDB | Ino | HMDB | Inosie | HMDB | Iso-prinosine | HMDB | Oxiamin | HMDB | Panholic-L | HMDB | Pantholic-L | HMDB | Ribonosine | HMDB | Selfer | HMDB | Trophicardyl | HMDB |
|
---|
Chemical Formula | C10H12N4O5 |
---|
Average Molecular Weight | 268.23 |
---|
Monoisotopic Molecular Weight | 268.0808 |
---|
IUPAC Name | 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one |
---|
Traditional Name | inosine |
---|
CAS Registry Number | 58-63-9 |
---|
SMILES | OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(O)N=CN=C12 |
---|
InChI Identifier | 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 |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. |
---|
Kingdom | Organic compounds |
---|
Super Class | Nucleosides, nucleotides, and analogues |
---|
Class | Purine nucleosides |
---|
Sub Class | Not Available |
---|
Direct Parent | Purine nucleosides |
---|
Alternative Parents | |
---|
Substituents | - Purine nucleoside
- Glycosyl compound
- N-glycosyl compound
- 6-oxopurine
- Hypoxanthine
- Pentose monosaccharide
- Purinone
- Imidazopyrimidine
- Purine
- Pyrimidone
- Pyrimidine
- Monosaccharide
- N-substituted imidazole
- Vinylogous amide
- Tetrahydrofuran
- Heteroaromatic compound
- Azole
- Imidazole
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Alcohol
- Organonitrogen compound
- Organic nitrogen compound
- Organooxygen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Primary alcohol
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Industrial application: Biological role: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | 218 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 15.8 mg/mL | YALKOWSKY,SH & DANNENFELSER,RM (1992) | logP | -2.10 | HANSCH,C ET AL. (1995) |
|
---|
Predicted Properties | [] |
---|
Spectra |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | Inosine, non-derivatized, GC-MS Spectrum | splash10-0frt-0890000000-c0c5ebc2bbf12c1a7edf | Spectrum | GC-MS | Inosine, 4 TMS, GC-MS Spectrum | splash10-00di-9440000000-566aadb777ee03fb22fb | Spectrum | GC-MS | Inosine, 4 TMS, GC-MS Spectrum | splash10-0fsi-1690000000-364bf8794afeeff6ba51 | Spectrum | GC-MS | Inosine, non-derivatized, GC-MS Spectrum | splash10-0frt-0890000000-c0c5ebc2bbf12c1a7edf | Spectrum | GC-MS | Inosine, non-derivatized, GC-MS Spectrum | splash10-00di-9440000000-566aadb777ee03fb22fb | Spectrum | GC-MS | Inosine, non-derivatized, GC-MS Spectrum | splash10-0fsi-1690000000-364bf8794afeeff6ba51 | Spectrum | Predicted GC-MS | Inosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0adl-9250000000-d6ee10ae0804bda3e4ce | Spectrum | Predicted GC-MS | Inosine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0lmr-8659500000-9f567e118aa09e880541 | Spectrum | Predicted GC-MS | Inosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TMS_4_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Inosine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-014r-0490020000-6eeacbf0ca8726ed8542 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-9100000000-cdcc2e477ba37ca8f07a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-f96733a8f63a90d3644d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0002-0900000000-b9b05cbee9a42ce87c0f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-015i-0696011000-c836d8cd13395c898ae1 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-0006-9100000000-d8c6fdb9231ac2c6e939 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0900000000-632ba91cd477e5aaf9e5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative | splash10-001i-0910000000-fc11279b73334e4ea0a8 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0090000000-00981efb4a9571473866 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-014i-0390000000-989ff580a7b60b151996 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-0920000000-b78cba83cbf8f1ae48f3 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-000i-0910000000-505a6507fcb525fe9a14 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-052r-2900000000-33d1372d34f6b06e3a2f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-000i-0930000000-9285a36e16cdf00b3f71 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0090000000-00981efb4a9571473866 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0390000000-989ff580a7b60b151996 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-0920000000-b78cba83cbf8f1ae48f3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-0910000000-c6d9b3470f4bf20f2031 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-052r-2900000000-33d1372d34f6b06e3a2f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-000i-0900000000-cb192ec0941c4e4f04b1 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0006-9100000000-1b4c3c2319fbba7de36b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-001i-0900000000-cc8e5ee2239e2de92705 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0006-9100000000-d8c6fdb9231ac2c6e939 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-001i-0900000000-632ba91cd477e5aaf9e5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-0930000000-6d3be934cd4b9ed750dd | 2017-09-14 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
|
---|
Pathways |
---|
Pathways | Name | SMPDB/Pathwhiz | KEGG | Purine Metabolism | | | Adenosine Deaminase Deficiency | | Not Available | Adenylosuccinate Lyase Deficiency | | Not Available | Gout or Kelley-Seegmiller Syndrome | | Not Available | Lesch-Nyhan Syndrome (LNS) | | Not Available |
|
---|
Protein Targets |
---|
Enzymes | |
---|
Transporters | |
Equilibrative nucleoside transporter 4 | SLC29A4 | 7p22.1 | Q7RTT9 | details |
|
---|
Metal Bindings | |
---|
Receptors | |
---|
Transcriptional Factors | Not Available |
---|
Concentrations Data |
---|
| Not Available |
---|
External Links |
---|
HMDB ID | HMDB0000195 |
---|
DrugBank ID | DB04335 |
---|
Phenol Explorer Compound ID | Not Available |
---|
FoodDB ID | FDB011802 |
---|
KNApSAcK ID | C00019692 |
---|
Chemspider ID | 5799 |
---|
KEGG Compound ID | C00294 |
---|
BioCyc ID | INOSINE |
---|
BiGG ID | 34525 |
---|
Wikipedia Link | Inosine |
---|
METLIN ID | 84 |
---|
PubChem Compound | 6021 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 17596 |
---|
References |
---|
General References | Not Available |
---|