Livestock Metabolome Database: Showing metabocard for Xanthine (LMDB00130)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:01 UTC

Update Date

2016-07-20 20:51:00 UTC

Lmdb

LMDB00130

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Xanthine

Description

Xanthine, also known as Xan or 2,6-dioxopurine, 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. An oxopurine in which the purine ring is substituted by oxo groups at positions 2 and 6 and N-9 is protonated. Xanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthine exists in all living species, ranging from bacteria to humans. Within humans, xanthine participates in a number of enzymatic reactions. In particular, xanthine can be biosynthesized from guanine; which is mediated by the enzyme guanine deaminase. In addition, xanthine and ribose 1-phosphate can be biosynthesized from xanthosine through the action of the enzyme purine nucleoside phosphorylase. In humans, xanthine is involved in azathioprine action pathway. Xanthine is a potentially toxic compound. Xanthine, with regard to humans, has been found to be associated with several diseases such as hydrocephalus, adenosine kinase deficiency, xanthinuria type II, and eosinophilic esophagitis; xanthine has also been linked to the inborn metabolic disorder lesch-nyhan syndrome.

Structure

MOL SDF 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

Chemical Formula

C₅H₄N₄O₂

Average Molecular Weight

152.1109

Monoisotopic Molecular Weight

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	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	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-0924000000-9b80e0a2a60c73ca0180	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f6t-0924000000-30dc5892eecde860846a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kai-7900000000-2dc30b0fc4cff2239dbe	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0900000000-a70539989d121bfacee0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-6900000000-b047b06406308dbaeda8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a4i-9300000000-ed480ed920c3e9b576ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0zfr-0900000000-efb049914c9bce596267	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-0900000000-efb049914c9bce596267	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0900000000-5fee91293851bb02193e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0900000000-4568a814903ff411923a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-e078a358156f5a04d4c1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-3900000000-250f7dc30d6fd96a4ef6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-0900000000-3a6dad2473c1654789f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-a4e9443b51c3ac2fc58b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-d23801a49488b1a5f0a2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-4900000000-b177a2a36043e5e87efc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-0900000000-cb3b35c3117b7f36bf5c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0900000000-8d2a19e7c37d2cb7658f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-05mo-9300000000-33d00ab2288aaa055517	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-1900000000-3a6dad2473c1654789f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-37e76df2401a85967caa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-0900000000-4132da06dda895afc3ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-2e9e069e2df414aed037	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w29-0900000000-fa52193346bc456d89e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5i-9400000000-bbf70998e8b7515cb440	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-566d663553ce4f0ec207	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-1900000000-d0a5d2c0f89f8d42d903	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-351d9f8ee3470f911829	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-7900000000-2d5ab5d5db8ff4981467	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Brain
Colostrum
Feces
Meat
Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Brain	Detected but not Quantified	Not Applicable	Not Available	Ovine	25959287	details
Colostrum	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Feces	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Meat	Detected but not Quantified	Not Applicable	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.26+/-0.02 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.29+/-0.02 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.38+/-0.02 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.45+/-0.03 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Ruminal Fluid	Detected and Quantified	59.9 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	91.7 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	116.6 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	177.6 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	68.7 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	101 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	137 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	155 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	117 +/- 71 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	178 +/- 60 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	60 +/- 16 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	60 +/- 16 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	85 +/- 23 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	92 +/- 20 uM	Not Available	Bovine	Saleem F, Bouatra...	details