inosine (CHEBI:17596)

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CHEBI:17596 - inosine

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ChEBI Name	inosine

ChEBI ID	CHEBI:17596

Definition	A purine nucleoside in which hypoxanthine is attached to ribofuranose via a β-N⁹-glycosidic bond.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:44407, CHEBI:5927, CHEBI:14456, CHEBI:24841

Supplier Information	eMolecules:29548306, eMolecules:522976, Selleckchem:inosine, ZINC000008855117

Download	Molfile XML SDF

more structures >>

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31 33 0 0 1 0 999 V2000

-1.1513 -0.1512 -0.5345 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.0679 -1.8319 0.6186 C 0 0 2 0 0 0 0 0 0 0 0 0

0.8094 -2.9528 0.5478 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.5490 -2.2405 0.5810 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.7413 -3.4200 -0.2021 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.2106 -1.0091 -0.0824 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.1346 -0.2277 0.8761 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.6865 0.9098 0.2242 O 0 0 0 0 0 0 0 0 0 0 0 0

0.0698 -0.8989 -0.6012 C 0 0 2 0 0 0 0 0 0 0 0 0

2.5351 -0.5940 -0.6256 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2719 -0.1108 -0.5938 N 0 0 0 0 0 0 0 0 0 0 0 0

1.4045 1.2286 -0.5594 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7699 1.5208 -0.5385 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8854 3.5292 -0.5050 C 0 0 0 0 0 0 0 0 0 0 0 0

3.4638 0.3765 -0.5825 N 0 0 0 0 0 0 0 0 0 0 0 0

3.1717 2.8665 -0.4815 C 0 0 0 0 0 0 0 0 0 0 0 0

4.3752 3.2048 -0.4412 O 0 0 0 0 0 0 0 0 0 0 0 0

2.2112 3.8285 -0.4696 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4862 2.2303 -0.5444 N 0 0 0 0 0 0 0 0 0 0 0 0

0.1382 -1.2696 1.5367 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5266 -3.5493 1.2712 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9183 -2.4475 1.5910 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7113 -3.5284 -0.2867 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7971 -1.3142 -0.9552 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.9508 -0.8721 1.2111 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5740 0.1036 1.7536 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.2504 1.3423 0.8985 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0610 -1.4789 -1.5315 H 0 0 0 0 0 0 0 0 0 0 0 0

2.7831 -1.5847 -0.6732 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1961 4.2810 -0.5009 H 0 0 0 0 0 0 0 0 0 0 0 0

4.5838 4.0595 -0.4005 H 0 0 0 0 0 0 0 0 0 0 0 0

1 6 1 0 0 0 0

1 9 1 0 0 0 0

6 4 1 0 0 0 0

4 2 1 0 0 0 0

2 9 1 0 0 0 0

2 3 1 0 0 0 0

4 5 1 0 0 0 0

6 7 1 0 0 0 0

7 8 1 0 0 0 0

9 11 1 0 0 0 0

12 11 4 0 0 0 0

10 11 4 0 0 0 0

10 15 4 0 0 0 0

15 13 4 0 0 0 0

19 12 4 0 0 0 0

12 13 4 0 0 0 0

13 16 4 0 0 0 0

18 14 4 0 0 0 0

18 16 4 0 0 0 0

14 19 4 0 0 0 0

16 17 1 0 0 0 0

2 20 1 0 0 0 0

3 21 1 0 0 0 0

4 22 1 0 0 0 0

5 23 1 0 0 0 0

6 24 1 0 0 0 0

7 25 1 0 0 0 0

7 26 1 0 0 0 0

8 27 1 0 0 0 0

9 28 1 0 0 0 0

10 29 1 0 0 0 0

14 30 1 0 0 0 0

17 31 1 0 0 0 0

M END): 16 ms

reading 31 atoms

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Wikipedia	License
Inosine is a nucleoside that is formed when hypoxanthine is attached to a ribose ring (also known as a ribofuranose) via a β-N9-glycosidic bond. It was discovered in 1965 in analysis of RNA transferase. Inosine is commonly found in tRNAs and is essential for proper translation of the genetic code in wobble base pair s. Knowledge of inosine metabolism has led to advances in immunotherapy in recent decades. Inosine monophosphate is oxidised by the enzyme inosine monophosphate dehydrogenase, yielding xanthosine monophosphate, a key precursor in purine metabolism. Mycophenolate mofetil is an anti-metabolite, anti-proliferative drug that acts as an inhibitor of inosine monophosphate dehydrogenase. It is used in the treatment of a variety of autoimmune diseases including granulomatosis with polyangiitis because the uptake of purine by actively dividing B cells can exceed 8 times that of normal body cells, and, therefore, this set of white cells (which cannot operate purine salvage pathways) is selectively targeted by the purine deficiency resulting from inosine monophosphate dehydrogenase (IMD) inhibition.
Read full article at Wikipedia

Formula

C10H12N4O5

Net Charge

Average Mass

268.22610

Monoisotopic Mass

268.08077

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

InChIKey

UGQMRVRMYYASKQ-KQYNXXCUSA-N

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(O)ncnc12

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	inosine (CHEBI:17596) has functional parent hypoxanthine (CHEBI:17368) inosine (CHEBI:17596) has functional parent ribofuranose (CHEBI:46998) inosine (CHEBI:17596) has role Escherichia coli metabolite (CHEBI:76971) inosine (CHEBI:17596) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) inosine (CHEBI:17596) has role human metabolite (CHEBI:77746) inosine (CHEBI:17596) has role mouse metabolite (CHEBI:75771) inosine (CHEBI:17596) is a inosines (CHEBI:24844) inosine (CHEBI:17596) is a purines D-ribonucleoside (CHEBI:142355)

Incoming	1-methylinosine (CHEBI:19065) has functional parent inosine (CHEBI:17596) 2ʼ-deoxyinosine (CHEBI:28997) has functional parent inosine (CHEBI:17596) 2'-O-methylinosine (CHEBI:68467) has functional parent inosine (CHEBI:17596) 3',5'-cyclic IMP (CHEBI:27541) has functional parent inosine (CHEBI:17596) 5'-S-methyl-5'-thioinosine (CHEBI:48595) has functional parent inosine (CHEBI:17596) 5'-deoxyinosine (CHEBI:82775) has functional parent inosine (CHEBI:17596) 6-O-methylinosine (CHEBI:70972) has functional parent inosine (CHEBI:17596) 6-deoxyinosine 5'-phosphate (CHEBI:45262) has functional parent inosine (CHEBI:17596) 7-methylinosine (CHEBI:70971) has functional parent inosine (CHEBI:17596) Phosphoric acid mono-[(2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester (CHEBI:193717) has functional parent inosine (CHEBI:17596)

IUPAC Names

(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-3,4-diol

9-(β-D-ribofuranosyl)-9H-purin-6-ol

inosine

INNs	Sources
inosina	ChemIDplus
inosine	ChemIDplus
inosinum	ChemIDplus

Synonyms	Sources
9-β-D-ribofuranosyl-9H-purin-6-ol	IUPAC
9-β-D-ribofuranosylhypoxanthine	NIST Chemistry WebBook
hypoxanthine D-riboside	ChemIDplus
hypoxanthosine	ChemIDplus
i	ChEBI
Inosin	ChEBI
Inosine	KEGG COMPOUND
INOSINE	PDBeChem
inosine	UniProt

Manual Xrefs	Databases
3301	DrugCentral
C00019692	KNApSAcK
C00294	KEGG COMPOUND
D00054	KEGG DRUG
ECMDB00195	ECMDB
HMDB0000195	HMDB
Inosine	Wikipedia
INOSINE	MetaCyc
NOS	PDBeChem
YMDB00510	YMDB
View more database links

Registry Numbers	Types	Sources
489332	Gmelin Registry Number	Gmelin
58-63-9	CAS Registry Number	ChemIDplus
58-63-9	CAS Registry Number	NIST Chemistry WebBook
624889	Reaxys Registry Number	Reaxys

Citation

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]

Last Modified

22 February 2017

CHEBI:17596 - inosine

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