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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:30:02 UTC
Update Date2021-09-26 23:15:54 UTC
HMDB IDHMDB0258766
Secondary Accession NumbersNone
Metabolite Identification
Common NameTebupirimfos
DescriptionTebupirimfos, also known as phostebupirim, belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom. Based on a literature review very few articles have been published on Tebupirimfos. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tebupirimfos is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tebupirimfos 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
O-(2-(1,1-Dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) phosphorothioateChEBI
O-(2-Tert-butylpyrimidin-5-yl) O-ethyl O-isopropyl thiophosphateChEBI
Phosphorothioic acid, O-(2-(1,1-dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) esterChEBI
PhostebupirimChEBI
TebupirimphosChEBI
O-(2-(1,1-Dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) phosphorothioic acidGenerator
O-(2-Tert-butylpyrimidin-5-yl) O-ethyl O-isopropyl thiophosphoric acidGenerator
Phosphorothioate, O-(2-(1,1-dimethylethyl)-5-pyrimidinyl) O-ethyl O-(1-methylethyl) esterGenerator
Chemical FormulaC13H23N2O3PS
Average Molecular Weight318.372
Monoisotopic Molecular Weight318.116699814
IUPAC NameO-2-tert-butylpyrimidin-5-yl O-ethyl O-propan-2-yl phosphorothioate
Traditional NameO-2-tert-butylpyrimidin-5-yl O-ethyl O-isopropyl phosphorothioate
CAS Registry NumberNot Available
SMILES
CCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C
InChI Identifier
InChI=1S/C13H23N2O3PS/c1-7-16-19(20,17-10(2)3)18-11-8-14-12(15-9-11)13(4,5)6/h8-10H,7H2,1-6H3
InChI KeyAWYOMXWDGWUJHS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrimidinyl phosphorothioates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where R= pyrimidine, R' = organyl group , and R\" = any atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentPyrimidinyl phosphorothioates
Alternative Parents
Substituents
  • Pyrimidinyl phosphorothioate
  • Thiophosphate triester
  • Pyrimidine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
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
logP4.4ALOGPS
logP4.37ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)0.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area53.47 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity84.77 m³·mol⁻¹ChemAxon
Polarizability33.21 ųChemAxon
Number of Rings1ChemAxon
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]+173.48530932474
DeepCCS[M-H]-171.12730932474
DeepCCS[M-2H]-204.01330932474
DeepCCS[M+Na]+179.57830932474
AllCCS[M+H]+170.532859911
AllCCS[M+H-H2O]+167.832859911
AllCCS[M+NH4]+172.932859911
AllCCS[M+Na]+173.632859911
AllCCS[M-H]-170.932859911
AllCCS[M+Na-2H]-171.532859911
AllCCS[M+HCOO]-172.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TebupirimfosCCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C2507.3Standard polar33892256
TebupirimfosCCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C1882.2Standard non polar33892256
TebupirimfosCCOP(=S)(OC(C)C)OC1=CN=C(N=C1)C(C)(C)C1819.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tebupirimfos GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kbb-3091000000-e482925bb6fcfc44353f2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tebupirimfos GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tebupirimfos 45V, Positive-QTOFsplash10-0udi-0950000000-69f7d979b099897396c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tebupirimfos 60V, Positive-QTOFsplash10-0udi-0910000000-38add9d4c6dc3c9b1dcb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tebupirimfos 30V, Positive-QTOFsplash10-004i-0290000000-176b5e76ef68801d23002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tebupirimfos 15V, Positive-QTOFsplash10-00or-0095000000-91a7dde839fb7669e0052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tebupirimfos 75V, Positive-QTOFsplash10-0udi-2900000000-3f567a576a7d1fa8d3d62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tebupirimfos 90V, Positive-QTOFsplash10-0zg0-5900000000-4c3cc7498ae0d242ad512021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tebupirimfos 10V, Positive-QTOFsplash10-004j-1291000000-4d0dc62832ebcc780ce42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tebupirimfos 20V, Positive-QTOFsplash10-0002-1290000000-9368f2f9b8099edef4a72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tebupirimfos 40V, Positive-QTOFsplash10-059l-9800000000-381851a99cde0191b3f92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tebupirimfos 10V, Negative-QTOFsplash10-00n0-0392000000-57fcec897ede61056ac42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tebupirimfos 20V, Negative-QTOFsplash10-002r-0290000000-9cc36c0cae92a541c6302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tebupirimfos 40V, Negative-QTOFsplash10-0002-3390000000-f5cdaf73ae60de86fbf32016-08-03Wishart 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 ID84419
KEGG Compound IDC18692
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTebupirimfos
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID38951
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 ]