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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 12:22:06 UTC
Update Date2021-09-26 23:06:54 UTC
HMDB IDHMDB0253594
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsazofos
DescriptionIsazofos, also known as miral or isazophos, belongs to the class of organic compounds known as aryl thiophosphates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where at least one R-group is an aryl group. Isazofos is an extremely weak basic (essentially neutral) compound (based on its pKa). Isazofos is a potentially toxic compound. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. This compound has been identified in human blood as reported by (PMID: 31557052 ). Isazofos is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Isazofos 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
MiralMeSH
IsazophosMeSH
Chemical FormulaC9H17ClN3O3PS
Average Molecular Weight313.741
Monoisotopic Molecular Weight313.041676334
IUPAC NameO-5-chloro-1-(propan-2-yl)-1H-1,2,4-triazol-3-yl O,O-diethyl phosphorothioate
Traditional NameO-5-chloro-1-isopropyl-1,2,4-triazol-3-yl O,O-diethyl phosphorothioate
CAS Registry NumberNot Available
SMILES
CCOP(=S)(OCC)OC1=NN(C(C)C)C(Cl)=N1
InChI Identifier
InChI=1S/C9H17ClN3O3PS/c1-5-14-17(18,15-6-2)16-9-11-8(10)13(12-9)7(3)4/h7H,5-6H2,1-4H3
InChI KeyXRHGWAGWAHHFLF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl thiophosphates. These are organic compounds containing the thiophosphoric acid functional group or a derivative thereof, with the general structure ROP(OR')(OR'')=S, where at least one R-group is an aryl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
Sub ClassThiophosphoric acid esters
Direct ParentAryl thiophosphates
Alternative Parents
Substituents
  • Aryl thiophosphate
  • Thiophosphate triester
  • Aryl chloride
  • Aryl halide
  • Azole
  • 1,2,4-triazole
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP3.88ALOGPS
logP3.48ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area58.4 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity87.58 m³·mol⁻¹ChemAxon
Polarizability29.88 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]+163.4730932474
DeepCCS[M-H]-161.11230932474
DeepCCS[M-2H]-193.99830932474
DeepCCS[M+Na]+169.56330932474
AllCCS[M+H]+164.032859911
AllCCS[M+H-H2O]+161.332859911
AllCCS[M+NH4]+166.532859911
AllCCS[M+Na]+167.332859911
AllCCS[M-H]-162.032859911
AllCCS[M+Na-2H]-162.732859911
AllCCS[M+HCOO]-163.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsazofosCCOP(=S)(OCC)OC1=NN(C(C)C)C(Cl)=N12538.5Standard polar33892256
IsazofosCCOP(=S)(OCC)OC1=NN(C(C)C)C(Cl)=N11800.3Standard non polar33892256
IsazofosCCOP(=S)(OCC)OC1=NN(C(C)C)C(Cl)=N11779.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isazofos GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9250000000-6574ab493c48c74b1d012021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isazofos GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-03di-5920000000-39a1603be495f91e7a402014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isazofos 45V, Positive-QTOFsplash10-02t9-0900000000-ea72f28796b6fbdf9d902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isazofos 60V, Positive-QTOFsplash10-02t9-0900000000-a2668fe42938247a7ded2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isazofos 30V, Positive-QTOFsplash10-03di-0910000000-9635b8c4ad3c0875cc482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isazofos 15V, Positive-QTOFsplash10-03di-0439000000-27f4323f205c519232172021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isazofos 75V, Positive-QTOFsplash10-02t9-0900000000-d39750082f86801c72382021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isazofos 90V, Positive-QTOFsplash10-03xr-1900000000-b9134554538d7bbcec902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isazofos 60V, Positive-QTOFsplash10-02t9-0900000000-e8cbbe0b08d9ba067fe52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 10V, Positive-QTOFsplash10-03di-1394000000-f11d28f4f84ffe1193992016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 20V, Positive-QTOFsplash10-0abc-6690000000-6e2e0358c2dcb15988462016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 40V, Positive-QTOFsplash10-0bt9-9210000000-b32b53b5e30f893885562016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 10V, Negative-QTOFsplash10-02tc-2921000000-a8986aaf072c88d737d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 20V, Negative-QTOFsplash10-00di-0790000000-fd94d04ba99c1649f06e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 40V, Negative-QTOFsplash10-03di-0390000000-3d37cacc7047d642f5672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 10V, Positive-QTOFsplash10-03di-0209000000-d65d4e7f6d3072dcb4e82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 20V, Positive-QTOFsplash10-03dr-0974000000-68e297723ccb029211dd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 40V, Positive-QTOFsplash10-014i-1900000000-7c92930d9e02b141b2dd2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 10V, Negative-QTOFsplash10-03di-0209000000-44924d59e6e012770dd62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 20V, Negative-QTOFsplash10-01x0-2932000000-d0586f2d64fb9a6fe0972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isazofos 40V, Negative-QTOFsplash10-001r-5900000000-aed99837cc10d7e91c732021-10-12Wishart 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 IDNot Available
KEGG Compound IDC19001
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound39223
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 ]