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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:34:48 UTC
Update Date2021-09-26 23:16:00 UTC
HMDB IDHMDB0258824
Secondary Accession NumbersNone
Metabolite Identification
Common NameTetraethyl pyrophosphate
Descriptiondiethyl [(diethoxyphosphoryl)oxy]phosphonate, also known as tetraethyl pyrophosphate, belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. Based on a literature review very few articles have been published on diethyl [(diethoxyphosphoryl)oxy]phosphonate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tetraethyl pyrophosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tetraethyl pyrophosphate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
Tetraethyl pyrophosphateKegg
Tetraethyl pyrophosphoric acidGenerator
Diethyl [(diethoxyphosphoryl)oxy]phosphonic acidGenerator
Diethoxyphosphoryl diethyl phosphoric acidGenerator
TEPPMeSH
Chemical FormulaC8H20O7P2
Average Molecular Weight290.189
Monoisotopic Molecular Weight290.06842698
IUPAC Namediethyl [(diethoxyphosphoryl)oxy]phosphonate
Traditional Nametetraethyl pyrophosphate
CAS Registry NumberNot Available
SMILES
CCOP(=O)(OCC)OP(=O)(OCC)OCC
InChI Identifier
InChI=1S/C8H20O7P2/c1-5-11-16(9,12-6-2)15-17(10,13-7-3)14-8-4/h5-8H2,1-4H3
InChI KeyIDCBOTIENDVCBQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic pyrophosphates
Direct ParentOrganic pyrophosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Dialkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP1.21ALOGPS
logP1.5ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-9.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area80.29 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity62.45 m³·mol⁻¹ChemAxon
Polarizability26.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+156.22430932474
DeepCCS[M-H]-153.86630932474
DeepCCS[M-2H]-187.61130932474
DeepCCS[M+Na]+162.60330932474
AllCCS[M+H]+166.232859911
AllCCS[M+H-H2O]+163.132859911
AllCCS[M+NH4]+169.032859911
AllCCS[M+Na]+169.832859911
AllCCS[M-H]-158.332859911
AllCCS[M+Na-2H]-159.532859911
AllCCS[M+HCOO]-160.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tetraethyl pyrophosphateCCOP(=O)(OCC)OP(=O)(OCC)OCC2377.8Standard polar33892256
Tetraethyl pyrophosphateCCOP(=O)(OCC)OP(=O)(OCC)OCC1613.8Standard non polar33892256
Tetraethyl pyrophosphateCCOP(=O)(OCC)OP(=O)(OCC)OCC1573.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tetraethyl pyrophosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0259-1790000000-2e55215098837767b88c2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetraethyl pyrophosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetraethyl pyrophosphate 10V, Positive-QTOFsplash10-01ox-1190000000-af40e87d657eb3a8c3cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetraethyl pyrophosphate 20V, Positive-QTOFsplash10-000i-0490000000-f765acee56e60827f18e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetraethyl pyrophosphate 40V, Positive-QTOFsplash10-004i-5930000000-6e5dfed923509b1dcae02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetraethyl pyrophosphate 10V, Negative-QTOFsplash10-000i-0090000000-46148bd46612b8d21c172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetraethyl pyrophosphate 20V, Negative-QTOFsplash10-03di-0190000000-3855703ca2b68d7033322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetraethyl pyrophosphate 40V, Negative-QTOFsplash10-0229-0960000000-bb79171ba757cb35c08c2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7585
KEGG Compound IDC19017
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]