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Bovine Rumen Metabolome Database



Showing metabocard for Xanthine (RMDB00292)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-13 14:34:00
Accession Number RMDB00292
Common Name Xanthine
Description 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.)
Synonyms
  1. 1H-Purine-2,6-diol
  2. 2,6(1,3)-Purinedion
  3. 2,6-Dihydroxypurine
  4. 2,6-Dioxopurine
  5. 3,7-Dihydro-1H-purine-2,6-dione
  6. 3,7-dihydropurine-2,6-dione
  7. 9H-Purine-2,6(1H,3H)-dione
  8. 9H-Purine-2,6-diol
  9. Dioxopurine
  10. Isoxanthine
  11. Pseudoxanthine
  12. Purine-2,6(1H,3H)-dione
  13. Purine-2,6-diol
  14. Xanthic oxide
  15. Xanthin
  16. Xanthine
Chemical IUPAC Name 2,6-dihydroxypurin
Chemical Formula C5H4N4O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Nucleosides and Nucleoside conjugates
Class
  • Purines and Purine Derivatives
Sub Class
  • Hydroxy purines
Family
  • Mammalian_Metabolite
Species
  • oxo(het)arene; aromatic compound; heterocyclic compound
Biofunction
  • Component of Purine metabolism
Application
Source
  • Endogenous
Average Molecular Weight 152.111
Monoisotopic Molecular Weight 152.033432
Isomeric SMILES O=C1NC(=O)C2=C(N1)N=CN2
Canonical SMILES O=C1NC(=O)C2=C(N1)N=CN2
KEGG Compound ID C00385 Link Image
BioCyc ID XANTHINE Link Image
BiGG ID 34825 Link Image
Wikipedia Link Xanthine Link Image
METLIN ID 82 Link Image
PubChem Compound 1188 Link Image
PubChem Substance 149179 Link Image
ChEBI ID 17712 Link Image
CAS Registry Number 69-89-6
InChI Identifier InChI=1/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11)
Synthesis Reference Procedure for the production of xanthine and xanthine-like materials. Fr. (1967), 4 pp.
Melting Point (Experimental) >300 oC
Experimental Water Solubility 0.069 mg/mL at 16 oC [MERCK INDEX [1996)]; 9.5 mg/mL (sodium salt, HMP experimental] Source: PhysProp
Predicted Water Solubility 4.91 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity -0.73 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity -0.65 [Predicted by ALOGPS]; -1.1 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1A96 Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • peroxisome
Biofluid Location
  • Cow_Milk
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 59.94 +/- 16.34 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 84.9 +/- 22.8 uM
Age N/A
Sex Female
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • Metabolomics reveals unhealthy alterations in rumen metabolism with increased proportion of cereal grain in the diet of dairy cows. Burim N. Ametaj, Qendrim Zebeli, Fozia Saleem, Nikolaos Psychogios, Michael J. Lewis, Suzanna M. Dunn, Jianguo Xia and David S. Wishart Metabolomics 2010;6(4):583-594
Concentrations (Abnormal)
Biofluid Rumen
Value 92 +/- 20 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 117 +/- 71 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 178 +/- 60 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Xanthine dehydrogenase/oxidase
Enzyme 1 [top]
Enzyme 1 ID 603
Enzyme 1 Name Xanthine dehydrogenase/oxidase
Enzyme 1 Synonyms
  1. Xanthine dehydrogenase
  2. XD
  3. Xanthine oxidase
  4. XO
  5. Xanthine oxidoreductase
Enzyme 1 Gene Name XDH
Enzyme 1 Protein Sequence >Xanthine dehydrogenase/oxidase
MTADELVFFVNGKKVVEKNADPETTLLAYLRRKLGLRGTKLGCGEGGCGACTVMLSKYDR
LQDKIIHFSANACLAPICTLHHVAVTTVEGIGSTKTRLHPVQERIAKSHGSQCGFCTPGI
VMSMYTLLRNQPEPTVEEIEDAFQGNLCRCTGYRPILQGFRTFAKNGGCCGGNGNNPNCC
MNQKKDHTVTLSPSLFNPEEFMPLDPTQEPIFPPELLRLKDVPPKQLRFEGERVTWIQAS
TLKELLDLKAQHPEAKLVVGNTEIGIEMKFKNQLFPMIICPAWIPELNAVEHGPEGISFG
AACALSSVEKTLLEAVAKLPTQKTEVFRGVLEQLRWFAGKQVKSVASLGGNIITASPISD
LNPVFMASGTKLTIVSRGTRRTVPMDHTFFPSYRKTLLGPEEILLSIEIPYSREDEFFSA
FKQASRREDDIAKVTCGMRVLFQPGSMQVKELALCYGGMADRTISALKTTQKQLSKFWNE
KLLQDVCAGLAEELSLSPDAPGGMIEFRRTLTLSFFFKFYLTVLKKLGKDSKDKCGKLDP
TYTSATLLFQKDPPANIQLFQEVPNGQSKEDTVGRPLPHLAAAMQASGEAVYCDDIPRYE
NELFLRLVTSTRAHAKIKSIDVSEAQKVPGFVCFLSADDIPGSNETGLFNDETVFAKDTV
TCVGHIIGAVVADTPEHAERAAHVVKVTYEDLPAIITIEDAIKNNSFYGSELKIEKGDLK
KGFSEADNVVSGELYIGGQDHFYLETHCTIAIPKGEEGEMELFVSTQNAMKTQSFVAKML
GVPVNRILVRVKRMGGGFGGKETRSTLVSVAVALAAYKTGHPVRCMLDRNEDMLITGGRH
PFLARYKVGFMKTGTIVALEVDHYSNAGNSRDLSHSIMERALFHMDNCYKIPNIRGTGRL
CKTNLSSNTAFRGFGGPQALFIAENWMSEVAVTCGLPAEEVRWKNMYKEGDLTHFNQRLE
GFSVPRCWDECLKSSQYYARKSEVDKFNKENCWKKRGLCIIPTKFGISFTVPFLNQAGAL
IHVYTDGSVLVSHGGTEMGQGLHTKMVQVASKALKIPISKIYISETSTNTVPNSSPTAAS
VSTDIYGQAVYEACQTILKRLEPFKKKNPDGSWEDWVMAAYQDRVSLSTTGFYRTPNLGY
SFETNSGNAFHYFTYGVACSEVEIDCLTGDHKNLRTDIVMDVGSSLNPAIDIGQVEGAFV
QGLGLFTLEELHYSPEGSLHTRGPSTYKIPAFGSIPTEFRVSLLRDCPNKKAIYASKAVG
EPPLFLGASVFFAIKDAIRAARAQHTNNNTKELFRLDSPATPEKIRNACVDKFTTLCVTG
APGNCKPWSLRV
Enzyme 1 Number of Residues 1332
Enzyme 1 Molecular Weight 146789.3
Enzyme 1 Theoretical pI 7.78
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Nucleotide transport and metabolism
Enzyme 1 Specific Function This enzyme can be converted from the dehydrogenase form (D) to the oxidase form (O) irreversibly by proteolysis or reversibly through the oxidation of sulfhydryl groups
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 1321704 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P80457 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name XDH_BOVIN Link Image
Enzyme 1 PDB ID 1V97 Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >3999 bp
ATGACAGCAGATGAATTGGTTTTCTTTGTGAATGGCAAAAAGGTGGTGGAGAAAAATGCA
GATCCAGAAACAACCCTTTTGGCCTACCTGAGAAGAAAGTTGGGGCTGAGAGGAACCAAG
CTGGGCTGTGGAGAAGGGGGCTGTGGGGCTTGTACAGTGATGCTTTCCAAGTATGATCGT
CTCCAAGACAAGATCATCCACTTTTCTGCCAATGCCTGCCTGGCTCCCATCTGCACCTTG
CACCACGTGGCTGTGACGACTGTGGAAGGAATTGGAAGCACCAAGACGAGGCTGCATCCT
GTGCAGGAGAGAATCGCCAAAAGTCACGGCTCTCAGTGTGGGTTCTGCACCCCCGGCATC
GTCATGAGCATGTACACACTGCTTCGGAATCAGCCCGAGCCCACTGTTGAAGAAATCGAG
GATGCTTTCCAAGGAAACTTATGCCGCTGTACAGGCTACAGACCCATCCTCCAGGGCTTC
CGGACCTTTGCCAAGAATGGTGGATGCTGTGGAGGAAATGGGAACAACCCAAACTGCTGC
ATGAACCAGAAGAAAGACCACACCGTTACTCTCTCACCATCTTTATTCAACCCAGAGGAG
TTCATGCCCCTGGATCCTACCCAGGAACCCATCTTCCCTCCAGAGTTGCTGAGGCTGAAA
GACGTTCCACCGAAGCAGCTGCGTTTTGAAGGGGAGCGTGTGACCTGGATCCAAGCCTCC
ACCTTGAAGGAGTTGCTGGACCTCAAAGCTCAGCATCCCGAGGCCAAGCTGGTGGTGGGG
AACACAGAGATCGGCATTGAGATGAAGTTTAAGAATCAGCTATTTCCTATGATCATCTGC
CCAGCCTGGATCCCTGAGCTGAATGCAGTGGAGCACGGACCTGAGGGGATCTCCTTTGGA
GCTGCTTGTGCCCTGAGCTCTGTGGAAAAGACCCTGCTCGAGGCCGTTGCCAAGCTTCCC
ACCCAGAAAACGGAGGTGTTCAGAGGAGTCCTGGAGCAGCTGCGCTGGTTCGCTGGGAAG
CAGGTCAAGTCTGTGGCGTCCCTTGGAGGGAACATCATCACAGCCAGCCCCATCTCTGAC
CTCAACCCTGTGTTCATGGCCAGTGGGACCAAGCTGACCATCGTGTCCAGAGGCACCAGA
AGAACAGTTCCAATGGACCACACCTTCTTCCCCAGCTACAGAAAGACCCTGCTGGGTCCA
GAGGAGATACTGCTCTCCATTGAGATCCCCTACAGCAGGGAGGATGAGTTTTTCTCAGCA
TTCAAGCAGGCAAGCCGGAGAGAAGATGACATAGCCAAGGTGACCTGCGGCATGAGAGTC
CTGTTCCAGCCAGGAAGCATGCAGGTAAAGGAGCTAGCCCTCTGCTATGGCGGAATGGCG
GACAGAACCATCTCAGCCCTCAAGACCACGCAGAAGCAGCTGTCAAAGTTCTGGAATGAG
AAGCTGCTACAGGACGTGTGTGCAGGCCTGGCGGAAGAACTGTCCTTATCCCCAGACGCC
CCTGGAGGCATGATTGAATTCCGACGCACCCTCACCCTCAGCTTCTTCTTCAAGTTCTAC
CTGACAGTACTGAAGAAACTGGGCAAGGACTCGAAAGATAAGTGTGGTAAACTGGACCCC
ACCTACACCAGCGCCACTTTACTCTTTCAGAAACACCCTCCAGCCAACATCCAGCTCTTC
CAAGAGGTGCCCAATGGTCAGTCCAAGGAGGACACAGTGGGCCGGCCCCTGCCCCACCTG
GCCGCGGCCATGCAAGCCTCTGGGGAGGCCGTATACTGTGACGACATCCCTCGCTACGAG
AATGAGCTGTTCCTCCGGCTGGTCACCAGCACCCGGGCCCACGCCAAGATCAAGTCCATT
GATGTTTCAGAAGCTCAGAAAGTGCCAGGATTTGTTTGCTTTCTCTCTGCTGATGATATT
CCCGGGAGTAATGAAACCGGACTCTTTAATGATGAGACAGTCTTTGCGAAGGATACGGTG
ACTTGTGTTGGTCACATCATTGGTGCTGTGGTCGCTGACACCCCAGAACATGCAGAGAGA
GCTGCCCATGTAGTGAAAGTCACCTATGAGGATCTTCCTGCCATTATCACAATTGAGGAT
GCTATAAAAAATAATTCCTTTTATGGATCTGAGCTGAAGATTGAGAAAGGAGACCTCAAG
AAGGGGTTTTCAGAAGCAGATAATGTGGTTTCAGGTGAGCTGTACATTGGTGGCCAAGAC
CACTTCTACCTGGAGACTCACTGCACCATTGCTATCCCGAAAGGCGAGGAAGGGGAGATG
GAGCTCTTTGTGTCCACACAGAATGCCATGAAAACCCAGTCCTTTGTTGCAAAAATGTTG
GGGGTTCCAGTAAACCGGATTTTGGTCCGAGTGAAGAGAATGGGAGGAGGCTTTGGAGGG
AAGGAGACCCGGAGCACCCTGGTGTCTGTGGCTGTGGCCCTGGCTGCATACAAGACTGGA
CACCCGGTGCGCTGCATGCTGGATCGTAATGAGGATATGCTGATAACTGGCGGCAGACAC
CCCTTCTTGGCCAGATACAAGGTTGGCTTCATGAAGACAGGGACGATTGTGGCTCTAGAG
GTGGATCACTACAGCAATGCCGGGAACAGCCGGGACCTCTCTCACAGTATAATGGAACGA
GCTCTATTCCACATGGACAACTGCTATAAAATCCCCAACATCCGGGGCACTGGGCGGCTG
TGCAAGACCAACCTGTCCTCCAACACGGCCTTCCGGGGCTTTGGGGGGCCCCAGGCTCTG
TTCATTGCCGAGAACTGGATGAGCGAAGTTGCAGTGACCTGTGGGCTGCCTGCAGAGGAA
GTGCGGTGGAAGAACATGTACAAAGAAGGGGACCTGACCCACTTCAACCAGAGGCTTGAG
GGGTTCAGCGTGCCCAGGTGCTGGGATGAGTGCCTGAAGAGCTCTCAGTATTACGCTCGG
AAGAGTGAGGTCGACAAGTTCAACAAGGAGAATTGTTGGAAAAAGAGAGGATTGTGCATA
ATTCCTACCAAATTTGGAATAAGCTTCACAGTTCCTTTTCTAAATCAGGCAGGAGCCCTG
ATCCACGTATACACAGATGGCTCCGTGCTGGTGAGCCACGGGGGCACAGAGATGGGCCAA
GGCCTTCACACCAAGATGGTGCAGGTGGCCAGCAAAGCTCTGAAGATCCCCATCTCTAAG
ATCTATATCAGCGAGACGAGCACTAACACGGTGCCCAACTCCTCTCCCACGGCCGCCTCC
GTCAGTACCGACATCTATGGACAGGCCGTCTATGAAGCTTGCCAGACCATCCTGAAAAGG
TTGGAACCCTTCAAGAAAAAGAATCCTGATGGCTCCTGGGAAGACTGGGTCATGGCTGCC
TACCAGGATAGAGTGAGCTTATCTACCACTGGGTTTTACAGGACACCCAACCTTGGCTAC
AGCTTTGAGACCAACTCAGGGAATGCCTTCCACTATTTCACCTACGGGGTGGCTTGCTCA
GAAGTGGAAATTGACTGTTTGACAGGGGATCATAAGAACCTCCGTACAGACATTGTCATG
GATGTTGGCTCCAGTCTGAACCCTGCCATCGATATTGGACAGGTGGAAGGGGCGTTTGTC
CAGGGCCTGGGCCTCTTCACCCTGGAGGAGCTACACTATTCCCCTGAGGGGAGCCTGCAC
ACCCGCGGCCCCAGCACCTACAAGATCCCCGCGTTTGGCAGCATCCCCACAGAGTTCAGG
GTGTCCCTGCTTCGCGACTGCCCCAACAAGAAGGCCATCTATGCCTCCAAGGCGGTCGGG
GAGCCGCCCCTCTTCCTGGGCGCCTCCGTCTTCTTTGCCATCAAGGATGCCATCCGCGCG
GCTCGAGCTCAGCACACAAATAATAACACGAAGGAGCTCTTCCGGCTAGATAGCCCTGCC
ACCCCGGAGAAGATCCGCAATGCCTGCGTGGACAAGTTCACCACTCTGTGTGTCACTGGT
GCACCAGGAAACTGTAAACCCTGGTCTCTGAGGGTCTGA
Enzyme 1 GenBank Gene ID X83508 Link Image
Enzyme 1 GeneCard ID XDH Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:2
Enzyme 1 Locus 2p23.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available