MiMeDB: Showing metabocard for Xanthine (MMDBc0000092)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:30:04 UTC

Update Date

2024-04-30 19:31:03 UTC

Metabolite ID

MMDBc0000092

Metabolite Identification

Common Name

Xanthine

Description

Xanthine is a purine base found in most body tissues and fluids, certain plants, and some urinary calculi. It is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects (Dorland, 28th ed.). Xanthine is found to be associated with Lesch-Nyhan syndrome and xanthinuria type I, which are inborn errors of metabolism.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
2,6-Dihydroxypurine	ChEBI
2,6-Dioxo-1,2,3,6-tetrahydropurine	ChEBI
9H-Purine-2,6-(1H,3H)-dione	ChEBI
Purine-2(3H),6(1H)-dione	ChEBI
Xan	ChEBI
1H-Purine-2,6-diol	HMDB
2,6(1,3)-Purinedion	HMDB
2,6-Dioxopurine	HMDB
3,7-Dihydro-1H-purine-2,6-dione	HMDB
3,7-Dihydropurine-2,6-dione	HMDB
9H-Purine-2,6(1H,3H)-dione	HMDB
9H-Purine-2,6-diol	HMDB
Dioxopurine	HMDB
Isoxanthine	HMDB
Pseudoxanthine	HMDB
Purine-2,6(1H,3H)-dione	HMDB
Purine-2,6-diol	HMDB
Xanthic oxide	HMDB
Xanthin	HMDB

Molecular Formula

C₅H₄N₄O₂

Average Mass

152.1109

Monoisotopic Mass

152.033425392

IUPAC Name

2,3,6,7-tetrahydro-1H-purine-2,6-dione

Traditional Name

xanthine

CAS Registry Number

69-89-6

SMILES

O=C1NC2=C(NC=N2)C(=O)N1

InChI Identifier

InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)

InChI Key

LRFVTYWOQMYALW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

xanthine (CHEBI:17712 )
Purine alkaloids (C00385 )
a small molecule (XANTHINE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.91 g/L	ALOGPS
logP	-0.65	ALOGPS
logP	-0.21	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	7.95	ChemAxon
pKa (Strongest Basic)	-0.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.88 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	36.92 m³·mol⁻¹	ChemAxon
Polarizability	12.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0f6t-0924000000-9b80e0a2a60c73ca0180	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-0924000000-9b80e0a2a60c73ca0180	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-0924000000-30dc5892eecde860846a	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kai-7900000000-2dc30b0fc4cff2239dbe	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0900000000-a70539989d121bfacee0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-6900000000-b047b06406308dbaeda8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9300000000-ed480ed920c3e9b576ec	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0zfr-0900000000-efb049914c9bce596267	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-0900000000-efb049914c9bce596267	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0900000000-5fee91293851bb02193e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0900000000-4568a814903ff411923a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-e078a358156f5a04d4c1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-3900000000-250f7dc30d6fd96a4ef6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0900000000-3a6dad2473c1654789f6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-a4e9443b51c3ac2fc58b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-d23801a49488b1a5f0a2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-4900000000-b177a2a36043e5e87efc	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-0900000000-cb3b35c3117b7f36bf5c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-8d2a19e7c37d2cb7658f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-05mo-9300000000-33d00ab2288aaa055517	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-1900000000-3a6dad2473c1654789f6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-37e76df2401a85967caa	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-0900000000-4132da06dda895afc3ab	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-2e9e069e2df414aed037	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w29-0900000000-fa52193346bc456d89e8	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5i-9400000000-bbf70998e8b7515cb440	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-566d663553ce4f0ec207	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-1900000000-d0a5d2c0f89f8d42d903	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-351d9f8ee3470f911829	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-7900000000-2d5ab5d5db8ff4981467	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.7 MHz, DMSO-d6, experimental)		2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View 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)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Peroxisome

Biospecimen Locations

Bladder
Blood
Cerebrospinal Fluid (CSF)
Epidermis
Feces
Fibroblasts
Intestine
Kidney
Liver
Placenta
Prostate
Saliva
Skeletal Muscle
Testis
Urine

Tissue Locations

Bladder
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Placenta
Prostate
Skeletal Muscle
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191852	Xanthine dehydrogenase/oxidase	Unknown	P47989	Homo sapiens
MMDBp0192133	Hypoxanthine-guanine phosphoribosyltransferase	Unknown	P00492	Homo sapiens
MMDBp0192329	Guanine deaminase	Unknown	Q9Y2T3	Homo sapiens
MMDBp0193933	Purine nucleoside phosphorylase	Enzyme	P00491	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001394	Guanine	Ammonia	Not Available	Guanine Deaminase	VMH	30371894
MMDBr0002390	Water	Hydrogen Ion	Xanthine dehydrogenase	Xanthine Dehydrogenase, Peroxisomal	VMH	30371894
MMDBr0002391	Xanthine	Xanthine	Not Available	Xanthine Diffusion in Peroxisome	VMH	30371894
MMDBr0002392	Water	Hydrogen peroxide	Xanthine dehydrogenase	Xanthine Oxidase	VMH	30371894
MMDBr0002393	Water	Hydrogen peroxide	Xanthine dehydrogenase	Xanthine Oxidase, Peroxisomal	VMH	30371894
MMDBr0002536	Water	Hydrogen Ion	Xanthine dehydrogenase	Xanthine:NAD+ Oxidoreductase	VMH	2713424 8248161
MMDBr0002537	Water	Hydrogen peroxide	Xanthine dehydrogenase	Hypoxanthine:Oxygen Oxidoreductase	VMH	11993848 1643670 3010873 8343533
MMDBr0002575	Water	Hydrogen Ion	Not Available	Xanthine:NAD+ Oxidoreductase	VMH	11246119 12632927
MMDBr0002576	Water	Hydrogen peroxide	Xanthine dehydrogenase	Xanthine:Oxygen Oxidoreductase	VMH	16087479 1643670 16756494 18600557 8343533
MMDBr0005594	Xanthine	Xanthine	Not Available	Transport of Xanthine	VMH	30371894
MMDBr0007154	Hydrogen Ion	Hydrogen Ion	Not Available	Xanthine transport in via proton symport	VMH	30371894
MMDBr0007155	Water	D-Ribose	Not Available	Xanthosine hydrolase	VMH	30371894
MMDBr0007559	Phosphate	Ribose-1-phosphate	Not Available	Purine-Nucleoside Phosphorylase (Xanthosine)	VMH	30371894
MMDBr0007600	Pyrophosphate	Phosphoribosyl pyrophosphate	Not Available	Xanthine phosphoribosyltransferase, reversible	VMH	30371894
MMDBr0008192	Water	Hydrogen Ion	Not Available	Hypoxanthine dehydrogenase	VMH	30371894
MMDBr0010293	Phosphoribosyl pyrophosphate	Pyrophosphate	Not Available	Xanthine Phosphoribosyltransferase	VMH	30371894
MMDBr0010883	Hydrogen Ion	Hydrogen Ion	Not Available	Xanthine transport in via proton symport	VMH	30371894
MMDBr0010884	Phosphoribosyl pyrophosphate	Pyrophosphate	Not Available	Xanthine phosphoribosyltransferase	VMH	30371894
MMDBr0012943	diphosphate	Phosphoribosyl pyrophosphate	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0012944	Phosphoribosyl pyrophosphate	diphosphate	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	RHEA	34755880
MMDBr0013340	Guanine	Ammonium	Guanine deaminase	Deamination	RHEA	34755880
MMDBr0013341	Guanine	Ammonium	Guanine deaminase	Deamination	RHEA	34755880
MMDBr0013555	Water	Hydrogen Ion	Xanthine dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0014471	Water	Hydrogen Ion	Xanthine dehydrogenase	Dehydrogenation	RHEA	34755880
MMDBr0014707	Phosphate	Ribose-1-phosphate	Pyrimidine/purine nucleoside phosphorylase	Phosphorylation	RHEA	34755880
MMDBr0014984	7-Methylxanthine	Formaldehyde	Probable methylxanthine N7-demethylase NdmC	Demethylation	RHEA	34755880
MMDBr0014985	7-Methylxanthine	Formaldehyde	Probable methylxanthine N7-demethylase NdmC	Demethylation	RHEA	34755880
MMDBr0014992	3-Methylxanthine	Formaldehyde	Methylxanthine N3-demethylase NdmB	Demethylation	RHEA	34755880
MMDBr0015488	3-Methylxanthine	Formaldehyde	Methylxanthine N3-demethylase NdmB	Demethylation	RHEA	34755880
MMDBr0015890	alpha-Ketoglutarate	Carbon dioxide	Alpha-ketoglutarate-dependent xanthine dioxygenase xanA	Oxygenation	RHEA	34755880
MMDBr0015891	alpha-Ketoglutarate	Carbon dioxide	Alpha-ketoglutarate-dependent xanthine dioxygenase xanA	Oxygenation	RHEA	34755880
MMDBr0016350	Hydrogen Ion	Ammonium	Cytosine deaminase	Deamination	RHEA	34755880
MMDBr0019314	Xanthosine	Xanthine	Purine nucleoside phosphorylase 2	Phosphorylation	PathBank	31602464
MMDBr0019334	Xanthine	Xanthylic acid	Xanthine-guanine phosphoribosyltransferase	Transfer of a ribosyl group	PathBank	31602464
MMDBr0019349	Hypoxanthine	Xanthine	Putative xanthine dehydrogenase molybdenum-binding subunit XdhA	Dehydrogenation	PathBank	31602464
MMDBr0019350	Xanthine	Hydrogen Ion	Putative xanthine dehydrogenase molybdenum-binding subunit XdhA	Dehydrogenation	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
3-methyl-crotonyl-glycinuria	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	11893004
Canavan disease	Increased	Association	Human Blood	HMDB	16139832
Degenerative disc disease	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	6656991
Hydrocephalus	Slight Decrease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	2611770
Lesch-nyhan syndrome	Increased	Association	Human Blood	HMDB	15965771
Lesch-nyhan syndrome	Slight Increase	Association	Human Blood	HMDB	3148065
Lesch-nyhan syndrome		Association	Human Blood	HMDB	11307586
Lesch-nyhan syndrome	Increased	Association	Human Urine	HMDB	11307586
Uremia	Increased	Association	Human Blood	HMDB	12675874
Eosinophilic esophagitis	Slight Decrease	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	743	Human ; Human supragingival plaque; Human feces; Human stool; Human urine; Human pleural fluid plaque; Pig ; Human sputum; Human subgingival plaque; Human saliva; Human mucosa; Cattle	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	488	Human feces; Human urine; Human ; Human mucosa; Human stool; Human supragingival plaque; Human saliva; Human subgingival plaque; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Chicken	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	187	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	194	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	7	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	5	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	24	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	4		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria/NULL	Proteobacteria	1	Human feces; Human urine; Human ; Human mucosa; Human stool; Human supragingival plaque; Human saliva; Human subgingival plaque; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Chicken	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Chloroflexi	2
Bacteria	Deinococcus-thermus	3
Eukaryota/Fungi	Ascomycota	7	Human feces; Human saliva	Unknown
Bacteria	Chlorobi	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	19.6				uM	Children (1 - 13 years old)	Not Specified	Isolated 3-Methylcrotonyl-CoA Carboxylase Deficiency	HMDB	11893004
Human Urine	Detected and Quantified	4.9				umol/mmol creatinine	Adolescent (13-18 years old)	Female	Adenosine kinase deficiency	HMDB	21963049
Human Urine	Detected and Quantified	6.8				umol/mmol creatinine	Adult (>18 years old)	Male	Adenosine kinase deficiency	HMDB	21963049
Human Blood	Detected and Quantified	6.37	1.95			uM	Adult (>18 years old)	Both	Canavan disease	HMDB	16139832
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.30		2.10	2.50	uM	Adult (>18 years old)	Both	Degenerative disc disease	HMDB	6656991
Human Cerebrospinal fluid (csf)	Detected and Quantified	5.17		3.64	6.70	uM	Adult (>18 years old)	Both	Hydrocephalus	HMDB	2611770
Human Cerebrospinal fluid (csf)	Detected and Quantified	9.90		7.46	12.3	uM	Children (1-13 years old)	Both	Hydrocephalus	HMDB	2611770
Human Blood	Detected and Quantified	118				uM	Adult (>18 years old)	Male	Lesch-Nyhan syndrome	HMDB	15965771
Human Blood	Detected and Quantified	2.2	0.3			uM	Adult (>18 years old)	Both	Lesch-Nyhan syndrome	HMDB	3148065
Human Blood	Detected and Quantified	2.7	1.6			uM	Adult (>18 years old)	Male	Lesch-Nyhan syndrome	HMDB	11307586
Human Urine	Detected and Quantified	31.657	19.220			umol/mmol creatinine	Adult (>18 years old)	Male	Lesch-Nyhan syndrome	HMDB	11307586
Human Blood	Detected and Quantified	18				uM	Infant (0-1 year old)	Female	Molybdenium co-factor deficiency	HMDB	3169394
Human Urine	Detected and Quantified	48				umol/mmol creatinine	Infant (0-1 year old)	Female	Molybdenium co-factor deficiency	HMDB	3169394
Human Urine	Detected and Quantified	259				umol/mmol creatinine	Children (1-13 years old)	Male	Molybdenium co-factor deficiency	HMDB	26644055
Human Urine	Detected and Quantified	228				umol/mmol creatinine	Children (1-13 years old)	Not Specified	Molybdenum cofactor deficiency	HMDB	8051926
Human Urine	Detected and Quantified	991				umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Molybdenum cofactor deficiency	HMDB	8051926
Human Urine	Detected and Quantified			529	1713	umol/mmol creatinine	Infant (0-1 year old)	Both	Molybdenum cofactor deficiency	HMDB	27289259
Human Blood	Detected and Quantified	1.1				uM	Adult (>18 years old)	Female	Phosphoribosylpyrophosphate Synthetase Superactivity	HMDB	12847698
Human Urine	Detected and Quantified	524.146				umol/mmol creatinine	Adult (>18 years old)	Female	Phosphoribosylpyrophosphate Synthetase Superactivity	HMDB	12847698
Human Urine	Detected and Quantified			1.6	3	umol/mmol creatinine	Infant (0-1 year old)	Both	Sulfite oxidase deficiency	HMDB	27289259
Human Urine	Detected and Quantified			12.9	34.9	umol/mmol creatinine	Children (1-13 years old)	Both	Sulfite oxidase deficiency	HMDB	15558695
Human Blood	Detected and Quantified	9.868	5.263			uM	Adult (>18 years old)	Both	Uremia	HMDB	12675874
Human Blood	Detected and Quantified	6.8				uM	Adult (>18 years old)	Female	Xanthinuria type 1	HMDB	3818951
Human Blood	Detected and Quantified	12.4				uM	Children (1-13 years old)	Male	Xanthinuria type 1	HMDB	3818951
Human Urine	Detected and Quantified	146.978				umol/mmol creatinine	Adult (>18 years old)	Female	Xanthinuria type 1	HMDB	3818951
Human Urine	Detected and Quantified	192.202				umol/mmol creatinine	Children (1-13 years old)	Male	Xanthinuria type 1	HMDB	3818951
Human Urine	Detected and Quantified	193				umol/mmol creatinine	Adult (>18 years old)	Male	Xanthinuria type 1	HMDB	23249873
Human Blood	Detected and Quantified			9	14	uM	Children (1-13 years old)	Both	Xanthinuria type 1	HMDB	25370766
Human Urine	Detected and Quantified			164.5	349.3	umol/mmol creatinine	Children (1-13 years old)	Both	Xanthinuria type 1	HMDB	25370766
Human Blood	Detected and Quantified	40				uM	Children (1-13 years old)	Male	Xanthinuria type II	HMDB	14627688
Human Urine	Detected and Quantified	4.3				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	30817767
Human Blood	Detected and Quantified	<1.00				uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15965771
Human Blood	Detected and Quantified	<2				uM	Infant (0-1 year old)	Not Specified	Normal	HMDB	3169394
Human Urine	Detected and Quantified	<30				umol/mmol creatinine	Not Specified	Not Specified	Normal	HMDB	21963049
Human Urine	Detected and Quantified	<40				umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	3169394
Human Urine	Detected and Quantified	<40				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	27289259
Human Urine	Detected and Quantified	<80				umol/mmol creatinine	Not Specified	Not Specified	Normal	HMDB	21963049
Human Urine	Detected and Quantified			0	30	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	23249873
Human Urine	Detected and Quantified			0	43	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	26644055
Human Blood	Detected and Quantified			0.3	3	uM	Children (1-13 years old)	Not Specified	Normal	HMDB	14627688
Human Blood	Detected and Quantified	0.7	0.2			uM	Adult (>18 years old)	Male	Normal	HMDB	11307586
Human Blood	Detected and Quantified	0.700	0.200			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	12847698
Human Saliva	Detected and Quantified	0.88	0.31			uM	Adult (>18 years old)	Both	Normal	HMDB	11310987
Human Blood	Detected and Quantified	0.9	0.1			uM	Adult (>18 years old)	Male	normal	HMDB	3818951
Human Blood	Detected and Quantified	0.91	0.45			uM	Adult (>18 years old)	Male	Normal	HMDB	16324927
Human Blood	Detected and Quantified	1.27	0.78			uM	Adult (>18 years old)	Both	Normal	HMDB	16139832
Human Saliva	Detected and Quantified	1.58	0.39			uM	Adult (>18 years old)	Both	Normal	HMDB	11310987
Human Saliva	Detected and Quantified	1.81	0.58			uM	Adult (>18 years old)	Both	Normal	HMDB	11310987
Human Cerebrospinal fluid (csf)	Detected and Quantified	13	7			uM	Adult (>18 years old)	Both	Normal	HMDB	18502700
Human Urine	Detected and Quantified	15.6	1.1			umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	15558695
Human Cerebrospinal fluid (csf)	Detected and Quantified	2.5	0.7			uM	Children (1 - 13 years old)	Not Specified	Normal	HMDB	11893004
Human Urine	Detected and Quantified	275.753	65.914			umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	12847698
Human Urine	Detected and Quantified	3.279	1.0175			umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	11307586
Human Blood	Detected and Quantified	3.289	9.211			uM	Adult (>18 years old)	Both	Normal	HMDB	12675874
Human Urine	Detected and Quantified	3.4	1.9			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15558695
Human Urine	Detected and Quantified	4.522	1.131			umol/mmol creatinine	Adult (>18 years old)	Male	normal	HMDB	3818951
Human Cerebrospinal fluid (csf)	Detected and Quantified	5.20		4.33	6.07	uM	Adult (>18 years old)	Both	Normal	HMDB	2611770
Human Urine	Detected and Quantified	37.779	61.348			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	52.591	67.878			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			3	62	umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified	200				uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	2.6		2.2	3.75	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	2.667		2.267	3.800	umol/mmol creatinine	Not Specified	Not Specified	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	4.5		2.7	8.0	uM	Adult (>18 years old)	Female	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	4.9	1.5			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	1.32	1.72			uM	Adult (>18 years old)	Both	Normal	HMDB	Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 10.1007/s11306-015-0840-5
Human Bladder	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Kidney	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Skeletal muscle	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22932811
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Adult (>18 years old)	Female	Normal	HMDB	26709303
Human Feces	Detected but not Quantified						Not Specified	Both	Normal	HMDB	25486321
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25496753
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000292

DrugBank ID

DB02134

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

1188

PDB ID

Not Available

ChEBI ID

17712

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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Niklasson F: Simultaneous liquid-chromatographic determination of hypoxanthine, xanthine, urate, and creatinine in cerebrospinal fluid, with direct injection. Clin Chem. 1983 Aug;29(8):1543-6. [PubMed:6872216 ]
Teeuwen HW, Elbers EL, van Rossum JM: Rapid and sensitive gas-chromatographic determination of caffeine in blood plasma, saliva, and xanthine beverages. Mol Biol Rep. 1991 Feb;15(1):1-7. doi: 10.1007/BF00369894. [PubMed:1875916 ]
Castro-Gago M, Rodriguez IN, Rodriguez-Nunez A, Guitian JP, Rocamonde SL, Rodriguez-Segade S: Therapeutic criteria in hydrocephalic children. Childs Nerv Syst. 1989 Dec;5(6):361-3. doi: 10.1007/BF00271893. [PubMed:2611770 ]
Kaya M, Moriwaki Y, Ka T, Inokuchi T, Yamamoto A, Takahashi S, Tsutsumi Z, Tsuzita J, Oku Y, Yamamoto T: Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise. Metabolism. 2006 Jan;55(1):103-7. doi: 10.1016/j.metabol.2005.07.013. [PubMed:16324927 ]
Liu Z, Li T, Wang E: Simultaneous determination of guanine, uric acid, hypoxanthine and xanthine in human plasma by reversed-phase high-performance liquid chromatography with amperometric detection. Analyst. 1995 Aug;120(8):2181-4. doi: 10.1039/an9952002181. [PubMed:7677251 ]
Becker MA, Kisicki J, Khosravan R, Wu J, Mulford D, Hunt B, MacDonald P, Joseph-Ridge N: Febuxostat (TMX-67), a novel, non-purine, selective inhibitor of xanthine oxidase, is safe and decreases serum urate in healthy volunteers. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1111-6. doi: 10.1081/NCN-200027372. [PubMed:15571211 ]
Kawasaki N, Tanimoto T, Tanaka A, Hayakawa T, Miyasaka N: Determination of non-protein-bound iron in human synovial fluid by high-performance liquid chromatography with electrochemical detection. J Chromatogr B Biomed Appl. 1994 Jun 17;656(2):436-40. doi: 10.1016/0378-4347(94)00135-9. [PubMed:7987499 ]
Cooper N, Khosravan R, Erdmann C, Fiene J, Lee JW: Quantification of uric acid, xanthine and hypoxanthine in human serum by HPLC for pharmacodynamic studies. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jun 6;837(1-2):1-10. doi: 10.1016/j.jchromb.2006.02.060. Epub 2006 May 2. [PubMed:16631418 ]
Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. doi: 10.1007/BF00965000. [PubMed:6656991 ]
Kiss A, Barenyi M, Csontai A: Xanthine stone in the urinary bladder of a male child. Urol Int. 1999;63(4):242-4. doi: 10.1159/000030458. [PubMed:10743702 ]
Kjaergaard N, Moller-Petersen JF, Kristiansen FV, Petersen PL, Ekelund S, Skovbo P: Xanthine and hypoxanthine in amniotic fluid during pregnancy. Dan Med Bull. 1990 Dec;37(6):559-60. [PubMed:2127397 ]
Wiley DM, Szabo I, Maguire MH, Finley BE, Bennett TL: Measurement of hypoxanthine and xanthine in late-gestation human amniotic fluid by reversed-phase high-performance liquid chromatography with photodiode-array detection. J Chromatogr. 1990 Nov 30;533:73-86. doi: 10.1016/s0378-4347(00)82188-x. [PubMed:2081781 ]
Gudbjornsson B, Zak A, Niklasson F, Hallgren R: Hypoxanthine, xanthine, and urate in synovial fluid from patients with inflammatory arthritides. Ann Rheum Dis. 1991 Oct;50(10):669-72. doi: 10.1136/ard.50.10.669. [PubMed:1958086 ]
Ginsburg I: Could synergistic interactions among reactive oxygen species, proteinases, membrane-perforating enzymes, hydrolases, microbial hemolysins and cytokines be the main cause of tissue damage in infectious and inflammatory conditions? Med Hypotheses. 1998 Oct;51(4):337-46. doi: 10.1016/s0306-9877(98)90059-7. [PubMed:9824842 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Xanthine (MMDBc0000092)

MOL for #<Metabolite:0x00007fe2a236ecf0>

3D MOL for #<Metabolite:0x00007fe2a236ecf0>

3D SDF for #<Metabolite:0x00007fe2a236ecf0>

3D-SDF for #<Metabolite:0x00007fe2a236ecf0>

PDB for #<Metabolite:0x00007fe2a236ecf0>

3D PDB for #<Metabolite:0x00007fe2a236ecf0>

SMILES for #<Metabolite:0x00007fe2a236ecf0>

INCHI for #<Metabolite:0x00007fe2a236ecf0>

Structure for #<Metabolite:0x00007fe2a236ecf0>

3D Structure for #<Metabolite:0x00007fe2a236ecf0>