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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:28:09 UTC
Update Date2021-09-26 23:15:53 UTC
HMDB IDHMDB0258744
Secondary Accession NumbersNone
Metabolite Identification
Common NameTaurolidine
DescriptionTaurolidine belongs to the class of organic compounds known as thiadiazinanes. These are organic heterocyclic compounds containing a six-membered saturated heterocycle with two nitrogen, one sulfur, and three carbon atoms. Based on a literature review a significant number of articles have been published on Taurolidine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Taurolidine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Taurolidine 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
Bis- (1,1-dioxoperhydro-1,2,4-thiadiazinyl-4)methaneMeSH
TauroflexMeSH
TaurolinMeSH
4,4'-Methylenebis-(tetrahydro-1,2,4-thiadiazine- 1,1-dioxide)MeSH
Bis(1,1-dioxo-perhydro-1,2,4-thiadiazinyl-4)methaneMeSH
TaurolineMeSH
Chemical FormulaC7H16N4O4S2
Average Molecular Weight284.35
Monoisotopic Molecular Weight284.061297359
IUPAC Name4-[(1,1-dioxo-1lambda6,2,4-thiadiazinan-4-yl)methyl]-1lambda6,2,4-thiadiazinane-1,1-dione
Traditional Name4-[(1,1-dioxo-1lambda6,2,4-thiadiazinan-4-yl)methyl]-1lambda6,2,4-thiadiazinane-1,1-dione
CAS Registry NumberNot Available
SMILES
O=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN1
InChI Identifier
InChI=1S/C7H16N4O4S2/c12-16(13)3-1-10(5-8-16)7-11-2-4-17(14,15)9-6-11/h8-9H,1-7H2
InChI KeyAJKIRUJIDFJUKJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiadiazinanes. These are organic heterocyclic compounds containing a six-membered saturated heterocycle with two nitrogen, one sulfur, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiadiazinanes
Sub ClassNot Available
Direct ParentThiadiazinanes
Alternative Parents
Substituents
  • Thiadiazinane
  • Organosulfonic acid amide
  • Organic sulfonic acid amide
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Azacycle
  • Aminal
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP-2.1ALOGPS
logP-2.5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.53ChemAxon
pKa (Strongest Basic)1.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.82 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.73 m³·mol⁻¹ChemAxon
Polarizability26.08 ųChemAxon
Number of Rings2ChemAxon
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]+149.2230932474
DeepCCS[M-H]-146.82430932474
DeepCCS[M-2H]-180.32930932474
DeepCCS[M+Na]+155.25730932474
AllCCS[M+H]+160.632859911
AllCCS[M+H-H2O]+157.232859911
AllCCS[M+NH4]+163.832859911
AllCCS[M+Na]+164.732859911
AllCCS[M-H]-155.332859911
AllCCS[M+Na-2H]-155.632859911
AllCCS[M+HCOO]-156.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TaurolidineO=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN13283.0Standard polar33892256
TaurolidineO=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN12734.7Standard non polar33892256
TaurolidineO=S1(=O)CCN(CN2CCS(=O)(=O)NC2)CN12833.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Taurolidine,1TMS,isomer #1C[Si](C)(C)N1CN(CN2CCS(=O)(=O)NC2)CCS1(=O)=O2693.6Semi standard non polar33892256
Taurolidine,1TMS,isomer #1C[Si](C)(C)N1CN(CN2CCS(=O)(=O)NC2)CCS1(=O)=O2631.7Standard non polar33892256
Taurolidine,1TMS,isomer #1C[Si](C)(C)N1CN(CN2CCS(=O)(=O)NC2)CCS1(=O)=O4469.7Standard polar33892256
Taurolidine,2TMS,isomer #1C[Si](C)(C)N1CN(CN2CCS(=O)(=O)N([Si](C)(C)C)C2)CCS1(=O)=O2710.3Semi standard non polar33892256
Taurolidine,2TMS,isomer #1C[Si](C)(C)N1CN(CN2CCS(=O)(=O)N([Si](C)(C)C)C2)CCS1(=O)=O2714.8Standard non polar33892256
Taurolidine,2TMS,isomer #1C[Si](C)(C)N1CN(CN2CCS(=O)(=O)N([Si](C)(C)C)C2)CCS1(=O)=O4122.6Standard polar33892256
Taurolidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(CN2CCS(=O)(=O)NC2)CCS1(=O)=O2884.1Semi standard non polar33892256
Taurolidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(CN2CCS(=O)(=O)NC2)CCS1(=O)=O2945.2Standard non polar33892256
Taurolidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(CN2CCS(=O)(=O)NC2)CCS1(=O)=O4611.2Standard polar33892256
Taurolidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(CN2CCS(=O)(=O)N([Si](C)(C)C(C)(C)C)C2)CCS1(=O)=O3076.9Semi standard non polar33892256
Taurolidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(CN2CCS(=O)(=O)N([Si](C)(C)C(C)(C)C)C2)CCS1(=O)=O3366.5Standard non polar33892256
Taurolidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CN(CN2CCS(=O)(=O)N([Si](C)(C)C(C)(C)C)C2)CCS1(=O)=O4214.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Taurolidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-8940000000-7b75be2f3e66c75e70512017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Taurolidine 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 - Taurolidine 10V, Positive-QTOFsplash10-000i-1190000000-9261932b0598a6eb5c7a2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taurolidine 20V, Positive-QTOFsplash10-0bvu-3960000000-ca2b0ea586790939b1452017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taurolidine 40V, Positive-QTOFsplash10-0a7j-9400000000-24d2cad45842aa4bf0942017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taurolidine 10V, Negative-QTOFsplash10-004i-9050000000-a65444728117f89684112017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taurolidine 20V, Negative-QTOFsplash10-056r-0950000000-0be64a075f5691e23e322017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taurolidine 40V, Negative-QTOFsplash10-01ox-9000000000-fb10f45568362c50bab52017-07-26Wishart 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 IDDB12473
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID27486
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTaurolidine
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 ]