Bovine Metabolome Database: Showing metabocard for Inosine (BMDB0000195)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:26:35 UTC

Update Date

2020-06-04 20:45:06 UTC

BMDB ID

BMDB0000195

Secondary Accession Numbers

BMDB00195

Metabolite Identification

Common Name

Inosine

Description

Inosine, also known as hypoxanthosine or panholic-L, 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. Inosine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Inosine exists in all living species, ranging from bacteria to humans. Inosine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

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

268.2261

Monoisotopic Molecular Weight

268.080769514

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

inosines (CHEBI:17596 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Lysosome
Mitochondria

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	-2.1	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	-2	ChemAxon
pKa (Strongest Acidic)	6.94	ChemAxon
pKa (Strongest Basic)	2.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	129.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	60.9 m³·mol⁻¹	ChemAxon
Polarizability	24.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Lysosome
Mitochondria

Biospecimen Locations

Brain
Colostrum
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Mammary Gland
Milk
Muscle
Neuron
Pancreas
Placenta
Platelet
Prostate Tissue
Semen
Spleen
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Erythrocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected and Quantified	833 +/- 140 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected and Quantified	0.970 +/- 0.420 uM	Not Specified	Not Specified	Normal	PMID: 1897275	details
Milk	Detected and Quantified	1 uM	Not Specified	Not Specified	Normal	PMID: 11242448	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Muscle	Detected and Quantified	301.14 +/- 26.11 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	356.78 +/- 41.47 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	395.56 +/- 38.59 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	427.49 +/- 33.47 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29634739	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Detected and Quantified	225 +/- 95 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000195

DrugBank ID

DB04335

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

6021

PDB ID

Not Available

ChEBI ID

17596

References

Synthesis Reference

Shi, Qingshan; Qiu, Yutang; Li, Liangqiu; Lin, Xiaoping. New inosine-producing bacterium and method for producing inosine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 6 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Schlimme E, Raezke KP, Ott FG: Ribonucleosides as minor milk constituents. Z Ernahrungswiss. 1991 Jun;30(2):138-52. [PubMed:1897275 ]
Schlimme E, Martin D, Meisel H: Nucleosides and nucleotides: natural bioactive substances in milk and colostrum. Br J Nutr. 2000 Nov;84 Suppl 1:S59-68. [PubMed:11242448 ]

Enzymes

Enzyme Details

1. Cytosolic purine 5'-nucleotidase

General function:: Involved in 5'-nucleotidase activity
Specific function:: May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:: NT5C2
Uniprot ID:: O46411
Molecular weight:: 64841.0

Reactions

Inosinic acid + Water → Inosine + Hydrogen phosphate	details

Enzyme Details

2. Purine nucleoside phosphorylase

General function:: Nucleotide transport and metabolism
Specific function:: The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:: PNP
Uniprot ID:: P55859
Molecular weight:: 32037.0

Reactions

Inosine + Hydrogen phosphate → Hypoxanthine + Ribose 1-phosphate	details

Enzyme Details

3. Adenosine deaminase

General function:: Nucleotide transport and metabolism
Specific function:: Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine (By similarity). Plays an important role in purine metabolism and in adenosine homeostasis (By similarity). Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events (By similarity). Acts as a positive regulator of T-cell coactivation, by binding DPP4 (By similarity). Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion (By similarity). Enhances dendritic cell immunogenicity by affecting dendritic cell costimulatory molecule expression and cytokines and chemokines secretion (PubMed:23240012). Enhances CD4+ T-cell differentiation and proliferation (By similarity). Acts as a positive modulator of adenosine receptors ADORA1 and ADORA2A, by enhancing their ligand affinity via conformational change (By similarity). Stimulates plasminogen activation (By similarity). Plays a role in male fertility (By similarity). Plays a protective role in early postimplantation embryonic development (By similarity).
Gene Name:: ADA
Uniprot ID:: P56658
Molecular weight:: 40919.0

Reactions

Adenosine + Water → Inosine + Ammonia	details

Showing metabocard for Inosine (BMDB0000195)

Structure for BMDB0000195 (Inosine)

Enzymes

Reactions

Reactions

Reactions