Bovine Metabolome Database: Showing metabocard for Hypoxanthine (BMDB0000157)

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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 22:20:17 UTC

Update Date

2020-06-04 20:52:01 UTC

BMDB ID

BMDB0000157

Secondary Accession Numbers

BMDB00157

Metabolite Identification

Common Name

Hypoxanthine

Description

Hypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Hypoxanthine exists as a solid, possibly soluble (in water), and a moderately basic compound (based on its pKa) molecule. Hypoxanthine exists in all living species, ranging from bacteria to humans. Hypoxanthine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6(1H)-Purinone	ChEBI
6-Oxopurine	ChEBI
9H-Purin-6(1H)-one	ChEBI
Hyp	ChEBI
Purin-6(1H)-one	ChEBI
Purine-6-ol	ChEBI
1,7-Dihydro-6H-purin-6-one	HMDB
1,7-Dihydro-6H-purine-6-one	HMDB
1H,7H-Hypoxanthine	HMDB
3H-Purin-6-ol	HMDB
4-Hydroxy-1H-purine	HMDB
6-Hydroxy-1H-purine	HMDB
6-Hydroxypurine	HMDB
7H-Purin-6-ol	HMDB
9H-Purin-6-ol	HMDB
Hypoxanthine enol	HMDB
Purin-6(3H)-one	HMDB
Purin-6-ol	HMDB
Sarcine	HMDB
Sarkin	HMDB
Sarkine	HMDB

Chemical Formula

C₅H₄N₄O

Average Molecular Weight

136.1115

Monoisotopic Molecular Weight

136.03851077

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

68-94-0

SMILES

Not Available

InChI Identifier

InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)

InChI Key

FDGQSTZJBFJUBT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Hypoxanthines

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Pyrimidone
Pyrimidine
Azole
Imidazole
Vinylogous amide
Heteroaromatic compound
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:17368 )
nucleobase analogue (CHEBI:17368 )
purine nucleobase (CHEBI:17368 )
Purine alkaloids (C00262 )
a purine-related compound (HYPOXANTHINE )
a purine base (HYPOXANTHINE )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Lysosome
Peroxisome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	150 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.7 mg/mL	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	-1.11	HANSCH,C ET AL. (1995)

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash Key

Biological Properties

Cellular Locations

Cytoplasm
Lysosome
Peroxisome

Biospecimen Locations

Adipose Tissue
Colostrum
Epidermis
Erythrocyte
Fibroblasts
Intestine
Kidney
Liver
Mammary Gland
Milk
Muscle
Placenta
Platelet
Prostate Tissue
Ruminal Fluid
Skeletal Muscle
Spleen
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Purine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	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
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	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 and Quantified	1227 +/- 156 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	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	7.1 uM	Not Specified	Not Specified	Normal	PMID: 6539345	details
Muscle	Detected and Quantified	1159.7 +/- 135.04 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Muscle	Detected and Quantified	1254.6 +/- 88.57 uM	Not Specified	Not Specified	Normal	PMID: 20831251	details
Muscle	Detected and Quantified	1497.99 +/- 57.51 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	678.18 +/- 58.48 uM	Not Specified	Not Specified	Normal	PMID: 20831251	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
Ruminal Fluid	Detected and Quantified	80 +/- 24 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	90 +/- 49 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	205 +/- 61 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	63 +/- 25 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	63 +/- 25 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25599412	details
Ruminal Fluid	Detected and Quantified	103-150 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Ruminal Fluid	Detected and Quantified	134 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	219 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	220 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	87.9 uM	Not Specified	Not Specified	Normal	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	753 +/- 191 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	52.27 +/- 24.11 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	76.1 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	85.1 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	205 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	52.3 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Detected and Quantified	176 +/- 66 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Ruminal Fluid	Detected and Quantified	205.04 +/- 58.59 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details

External Links

HMDB ID

HMDB0000157

DrugBank ID

DB04076

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

790

PDB ID

Not Available

ChEBI ID

17368

References

Synthesis Reference

Shaw, Elliott.New synthesis of the purines adenine, hypoxanthine, xanthine, and isoguanine. Journal of Biological Chemistry (1950), 185 439-47.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]

Enzymes

Enzyme Details

1. Hypoxanthine-guanine phosphoribosyltransferase

General function:: Nucleotide transport and metabolism
Specific function:: Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Plays a central role in the generation of purine nucleotides through the purine salvage pathway (By similarity).
Gene Name:: HPRT1
Uniprot ID:: Q3SZ18
Molecular weight:: 24498.0

Reactions

Inosinic acid + Pyrophosphate → Hypoxanthine + Phosphoribosyl pyrophosphate	details

Enzyme Details

2. Xanthine dehydrogenase/oxidase

General function:: Nucleotide transport and metabolism
Specific function:: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species.
Gene Name:: XDH
Uniprot ID:: P80457
Molecular weight:: 146790.0

Enzyme Details

3. 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
Deoxyinosine + Hydrogen phosphate → Hypoxanthine + Deoxyribose 1-phosphate	details

Showing metabocard for Hypoxanthine (BMDB0000157)

Structure for BMDB0000157 (Hypoxanthine)

Enzymes

Reactions

Reactions