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Showing Compound XMP (FDB031254)

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
MOLSDFPDBSMILESInChI
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-2ALOGPS
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-bce7ee60221f82790f352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-9400000000-05c1ae772c001a15a8c62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9200000000-743d2f19ea30c814c56a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9210000000-f36c079a2869c6c7c63d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9300000000-0cea344051256ed9d6422021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9300000000-1295bb6a6dfffef31dd22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-7125a3a52d3308d6b3672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-9400000000-f93509061523b8f0b0122021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9310000000-a910c200bfc66c8e1c462021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-1ff54bb8d71e1ea585f22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-03fs-9380000000-2a0fbd1929733b4918d12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-1039000000-f0bd4ff644ac799373012021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0913000000-d17f1d77b992fc6e9f042015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-efbdb918f50ba610575d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-cf070bd16aacd3dcb6fb2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imi-6509000000-d931cb1dcaeba678220c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbc-9300000000-e596281ec38113a9653c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-1caa46ecd17db343ddd32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ac450658003af6c0a1092021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-448bfe6677d2f8fe1f3c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-10c12403e596a9b5bf0a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3009000000-8a668987618bcd1531e72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-4b2bf772bc8415c9f24c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9201000000-907dd40cbb70b7a5c62d2021-09-23View Spectrum
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