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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:21:02 UTC
Update Date2021-09-26 23:15:46 UTC
HMDB IDHMDB0258670
Secondary Accession NumbersNone
Metabolite Identification
Common NameTabun
Description[(dimethylamino)(ethoxy)phosphoryl]formonitrile belongs to the class of organic compounds known as phosphonic acid esters. These are organic compounds containing phosphonic acid ester functional group, with the general structure ROP(=O)OH (R = organyl group). Based on a literature review very few articles have been published on [(dimethylamino)(ethoxy)phosphoryl]formonitrile. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tabun is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tabun 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
N,N-dimethylamido-O-Ethyl cyanophosphateMeSH
TabunMeSH
Chemical FormulaC5H11N2O2P
Average Molecular Weight162.129
Monoisotopic Molecular Weight162.0558146
IUPAC Name[(dimethylamino)(ethoxy)phosphoryl]formonitrile
Traditional Nametabun
CAS Registry NumberNot Available
SMILES
CCOP(=O)(C#N)N(C)C
InChI Identifier
InChI=1S/C5H11N2O2P/c1-4-9-10(8,5-6)7(2)3/h4H2,1-3H3
InChI KeyPJVJTCIRVMBVIA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphonic acid esters. These are organic compounds containing phosphonic acid ester functional group, with the general structure ROP(=O)OH (R = organyl group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassPhosphonic acid esters
Direct ParentPhosphonic acid esters
Alternative Parents
Substituents
  • Phosphonic amide ester
  • Phosphonic acid ester
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not 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
logP0.39ALOGPS
logP-0.12ChemAxon
logS-1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity39.07 m³·mol⁻¹ChemAxon
Polarizability15.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+131.95230932474
DeepCCS[M-H]-129.3330932474
DeepCCS[M-2H]-165.73730932474
DeepCCS[M+Na]+140.87630932474
AllCCS[M+H]+137.332859911
AllCCS[M+H-H2O]+133.532859911
AllCCS[M+NH4]+140.932859911
AllCCS[M+Na]+141.932859911
AllCCS[M-H]-132.932859911
AllCCS[M+Na-2H]-135.532859911
AllCCS[M+HCOO]-138.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TabunCCOP(=O)(C#N)N(C)C1776.6Standard polar33892256
TabunCCOP(=O)(C#N)N(C)C1112.5Standard non polar33892256
TabunCCOP(=O)(C#N)N(C)C1088.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tabun GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-4900000000-ed5ce9842bfd5eeebe812021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tabun 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 - Tabun 10V, Positive-QTOFsplash10-000i-0900000000-5a2d73d38739bce848352016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tabun 20V, Positive-QTOFsplash10-000m-9700000000-b5ab73084a2546d7c5f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tabun 40V, Positive-QTOFsplash10-0a4r-5900000000-cba7e4ae15f00fbb75af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tabun 10V, Negative-QTOFsplash10-001i-0900000000-178848bb31bb0ab99dd82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tabun 20V, Negative-QTOFsplash10-014i-3900000000-105c480c317f81037f292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tabun 40V, Negative-QTOFsplash10-004i-9500000000-ddb563201b1c552dc0e52016-08-03Wishart 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 ID6254
KEGG Compound IDNot Available
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 ]