Record Information
Version1.0
Creation date2015-05-07 21:26:59 UTC
Update date2019-11-26 03:22:13 UTC
Primary IDFDB031254
Secondary Accession Numbers
  • FDB022687
Chemical Information
FooDB NameXMP
DescriptionXanthylic acid, also known as xmp or (9-D-ribosylxanthine)-5'-phosphate, is a member of the class of compounds known as purine ribonucleoside monophosphates. Purine ribonucleoside monophosphates are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Xanthylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Xanthylic acid can be found in a number of food items such as common grape, black-eyed pea, java plum, and wild rice, which makes xanthylic acid a potential biomarker for the consumption of these food products. Xanthylic acid exists in all living species, ranging from bacteria to humans. In humans, xanthylic acid is involved in several metabolic pathways, some of which include azathioprine action pathway, glutamate metabolism, mercaptopurine action pathway, and purine metabolism. Xanthylic acid is also involved in several metabolic disorders, some of which include purine nucleoside phosphorylase deficiency, succinic semialdehyde dehydrogenase deficiency, xanthine dehydrogenase deficiency (xanthinuria), and molybdenum cofactor deficiency. Xanthosine monophosphate is an intermediate in purine metabolism. It is a ribonucleoside monophosphate. It is formed from IMP via the action of IMP dehydrogenase, and it forms GMP via the action of GMP synthaseand is) also, XMP can be released from XTP by enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase containing (d)XTPase activity .
CAS Number523-98-8
Structure
Thumb
Synonyms
SynonymSource
(9-D-Ribosylxanthine)-5'-phosphateChEBI
Xanthosine 5'-phosphateChEBI
Xanthosine monophosphateChEBI
XMPChEBI
(9-D-Ribosylxanthine)-5'-phosphoric acidGenerator
XanthylateGenerator
Xanthosine 5'-phosphoric acidGenerator
Xanthosine monophosphoric acidGenerator
5'-Xanthonylate monophosphateHMDB
Xanthosine-5'-PHMDB
Xanthosine-5'-phosphateHMDB
Xanthosine monophosphate, 8-(14)C-labeledMeSH, HMDB
Xanthosine 5'-monophosphateHMDB
Xanthosine 5’-monophosphateHMDB
Xanthosine 5’-phosphateHMDB
Xanthylic acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility2.49 g/LALOGPS
logP-1.9ALOGPS
logP-2.2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.26ChemAxon
pKa (Strongest Basic)0.069ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area192.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.08 m³·mol⁻¹ChemAxon
Polarizability29.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H13N4O9P
IUPAC name{[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1
InChI KeyDCTLYFZHFGENCW-UUOKFMHZSA-N
Isomeric SMILESO[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O
Average Molecular Weight364.2054
Monoisotopic Molecular Weight364.042014546
Classification
Description Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Xanthine
  • 6-oxopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Alkaloid or derivatives
  • Monoalkyl phosphate
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Vinylogous amide
  • Imidazole
  • Tetrahydrofuran
  • Lactam
  • 1,2-diol
  • Urea
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSXanthylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9613000000-3054f73e4c9456039ed6Spectrum
Predicted GC-MSXanthylic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-9521200000-1e6fc3c628d8ebd23b37Spectrum
Predicted GC-MSXanthylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0ik9-7964000000-bce7ee60221f82790f35Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9400000000-05c1ae772c001a15a8c6Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9200000000-743d2f19ea30c814c56aSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9210000000-f36c079a2869c6c7c63dSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9300000000-0cea344051256ed9d642Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-1295bb6a6dfffef31dd2Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-7125a3a52d3308d6b367Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9400000000-f93509061523b8f0b012Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9310000000-a910c200bfc66c8e1c46Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-1ff54bb8d71e1ea585f2Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03fs-9380000000-2a0fbd1929733b4918d1Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-1039000000-f0bd4ff644ac79937301Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0913000000-d17f1d77b992fc6e9f04Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-efbdb918f50ba610575dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-cf070bd16aacd3dcb6fbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-6509000000-d931cb1dcaeba678220cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbc-9300000000-e596281ec38113a9653cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-1caa46ecd17db343ddd3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ac450658003af6c0a109Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-448bfe6677d2f8fe1f3cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-10c12403e596a9b5bf0aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3009000000-8a668987618bcd1531e7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-4b2bf772bc8415c9f24cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9201000000-907dd40cbb70b7a5c62dSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference