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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 05:37:22 UTC
Update Date2021-09-14 15:38:59 UTC
HMDB IDHMDB0003834
Secondary Accession Numbers
  • HMDB03834
Metabolite Identification
Common NameP1,P4-Bis(5'-xanthosyl) tetraphosphate
DescriptionP1,P4-Bis(5'-xanthosyl) tetraphosphate, also known as XPPPPX, belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. P1,P4-Bis(5'-xanthosyl) tetraphosphate exists in all living organisms, ranging from bacteria to humans. P1,P4-Bis(5'-xanthosyl) tetraphosphate has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make P1,P4-bis(5'-xanthosyl) tetraphosphate a potential biomarker for the consumption of these foods. P1,P4-Bis(5'-xanthosyl) tetraphosphate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on P1,P4-Bis(5'-xanthosyl) tetraphosphate.
Structure
Data?1582752288
Synonyms
ValueSource
XPPPPXChEBI
P1,P4-Bis(5'-xanthosyl) tetraphosphoric acidGenerator
P1,P4-Bis(5'-xanthosyl) tetraphosphateChEBI
p(1),p(4)-Bis(5'-xanthosyl) tetraphosphoric acidGenerator, HMDB
Chemical FormulaC20H26N8O23P4
Average Molecular Weight870.3553
Monoisotopic Molecular Weight870.006125226
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}({[({[({[(2R,3S,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid
Traditional Name[(2R,3S,4R,5R)-5-(2,6-dioxo-1,3-dihydropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy[({[(2R,3S,4R,5R)-5-(2,6-dioxo-1,3-dihydropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphinic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(=O)NC3=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O
InChI Identifier
InChI=1S/C20H26N8O23P4/c29-9-5(47-17(11(9)31)27-3-21-7-13(27)23-19(35)25-15(7)33)1-45-52(37,38)49-54(41,42)51-55(43,44)50-53(39,40)46-2-6-10(30)12(32)18(48-6)28-4-22-8-14(28)24-20(36)26-16(8)34/h3-6,9-12,17-18,29-32H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,23,25,33,35)(H2,24,26,34,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
InChI KeyPNTZPNDMKHCLNV-MHARETSRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class(5'->5')-dinucleotides
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
Substituents
  • (5'->5')-dinucleotide
  • Purine ribonucleoside polyphosphate
  • Purine nucleotide sugar
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Xanthine
  • 6-oxopurine
  • Monosaccharide phosphate
  • Purinone
  • Imidazopyrimidine
  • Alkaloid or derivatives
  • Purine
  • Monoalkyl phosphate
  • Pyrimidone
  • Pyrimidine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Vinylogous amide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Urea
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.15 g/LALOGPS
logP0.46ALOGPS
logP-4.1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.59ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area446.77 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity164.13 m³·mol⁻¹ChemAxon
Polarizability66.69 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+217.81430932474
DeepCCS[M-H]-215.41930932474
DeepCCS[M-2H]-248.85430932474
DeepCCS[M+Na]+223.72730932474
AllCCS[M+H]+240.932859911
AllCCS[M+H-H2O]+241.132859911
AllCCS[M+NH4]+240.632859911
AllCCS[M+Na]+240.532859911
AllCCS[M-H]-245.932859911
AllCCS[M+Na-2H]-248.932859911
AllCCS[M+HCOO]-252.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
P1,P4-Bis(5'-xanthosyl) tetraphosphateO[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(=O)NC3=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O6621.1Standard polar33892256
P1,P4-Bis(5'-xanthosyl) tetraphosphateO[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(=O)NC3=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O3733.0Standard non polar33892256
P1,P4-Bis(5'-xanthosyl) tetraphosphateO[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(=O)NC3=O)O[C@H]([C@@H]1O)N1C=NC2=C1NC(=O)NC2=O7521.4Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 10V, Positive-QTOFsplash10-0udi-0910000030-d52a004351d0530c64af2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 20V, Positive-QTOFsplash10-0udi-0900000000-79901f61f2d5edad641a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 40V, Positive-QTOFsplash10-0udi-0900000000-4f8f39c1d5eeb9d638902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 10V, Negative-QTOFsplash10-0uxr-0400000090-7c67a90b7501b87e0c432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 20V, Negative-QTOFsplash10-0udl-7900020010-3e3839e585a01c58aa762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 40V, Negative-QTOFsplash10-0udi-3915110000-66ed29087f6d3514eaec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 10V, Positive-QTOFsplash10-0udi-0900000010-7c179368b74e956c72592021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 20V, Positive-QTOFsplash10-0uk9-0900000050-bc3f321e19a2ef93b2a72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 40V, Positive-QTOFsplash10-0udi-0900000000-1cd9c668347257d2aeaa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 10V, Negative-QTOFsplash10-014i-0000000190-f6777eff45f00300667a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 20V, Negative-QTOFsplash10-0uyi-1602181890-ab6af90ff99dc2b59f262021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - P1,P4-Bis(5'-xanthosyl) tetraphosphate 40V, Negative-QTOFsplash10-0f6x-1522791110-932397bd809683f3ee6c2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023233
KNApSAcK IDNot Available
Chemspider ID389293
KEGG Compound IDC04392
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440322
PDB IDNot Available
ChEBI ID28400
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis.
Gene Name:
NUDT2
Uniprot ID:
P50583
Molecular weight:
16829.09
Reactions
P1,P4-Bis(5'-xanthosyl) tetraphosphate + Water → Xanthosine 5-triphosphate + Xanthylic aciddetails