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Record Information
Version3.6
Creation Date2012-10-25 14:44:47 UTC
Update Date2016-02-11 07:48:48 UTC
HMDB IDHMDB59586
Secondary Accession NumbersNone
Metabolite Identification
Common NamePerfluorooctanesulfonic acid
DescriptionPerfluorooctanesulfonic acid or perfluorooctane sulfonate (PFOS), is a man-made fluorosurfactant and global pollutant. PFOS was the key ingredient in Scotchgard, a fabric protector made by 3M, and numerous stain repellents. It was added to Annex B of the Stockholm Convention on Persistent Organic Pollutants in May 2009. PFOS can form from the degradation of precursors in addition to industrial production. The PFOS levels that have been detected in wildlife are considered high enough to affect health parameters, and recently higher serum levels of PFOS were found to be associated with increased risk of chronic kidney disease in the general United States population, consistent with earlier animal studies.
Structure
Thumb
Synonyms
ValueSource
1-Perfluorooctanesulfonic acidChEBI
heptadecafluoro-1-Octanesulfonic acidChEBI
Perfluorooctylsulfonic acidChEBI
PFOSChEBI
1-PerfluorooctanesulfonateGenerator
1-PerfluorooctanesulphonateGenerator
1-Perfluorooctanesulphonic acidGenerator
PerfluorooctanesulfonateGenerator
PerfluorooctanesulphonateGenerator
Perfluorooctanesulphonic acidGenerator
heptadecafluoro-1-OctanesulfonateGenerator
heptadecafluoro-1-OctanesulphonateGenerator
heptadecafluoro-1-Octanesulphonic acidGenerator
PerfluorooctylsulfonateGenerator
PerfluorooctylsulphonateGenerator
Perfluorooctylsulphonic acidGenerator
Chemical FormulaC8HF17O3S
Average Molecular Weight500.13
Monoisotopic Molecular Weight499.937494073
IUPAC Nameheptadecafluorooctane-1-sulfonic acid
Traditional NamePFOS
CAS Registry NumberNot Available
SMILES
OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F
InChI Identifier
InChI=1S/C8HF17O3S/c9-1(10,3(13,14)5(17,18)7(21,22)23)2(11,12)4(15,16)6(19,20)8(24,25)29(26,27)28/h(H,26,27,28)
InChI KeyInChIKey=YFSUTJLHUFNCNZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as perfluorooctane sulfonic acid and derivatives. These are organic compounds containing an octyl chain attached to the sulfur of a sulfonic acid (or a derivative thereof), where all hydrogens of the octyl chain are replaced by fluorine atoms.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassAlkyl halides
Sub ClassAlkyl fluorides
Direct ParentPerfluorooctane sulfonic acid and derivatives
Alternative Parents
Substituents
  • Perfluorooctane sulfonic acid or derivatives
  • Alkanesulfonic acid
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonic acid
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organofluoride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.073 mg/mLALOGPS
logP4.24ALOGPS
logP5.43ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity50.98 m3·mol-1ChemAxon
Polarizability22.56 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.02260(0.02000-0.02520) uMAdult (>18 years old)BothNormal
    • Report on Human B...
details
BloodDetected and Quantified0.0194 (0.0169-0.0224) uMAdult (>18 years old)Not SpecifiedNormal
    • Report on Human B...
    • National Health a...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID67068
KEGG Compound IDC18142
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB59586
Metagene LinkHMDB59586
METLIN IDNot Available
PubChem Compound74483
PDB IDNot Available
ChEBI ID39421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available