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Record Information
Version3.6
Creation Date2013-03-15 15:57:54 UTC
Update Date2016-02-11 07:55:10 UTC
HMDB IDHMDB59911
Secondary Accession NumbersNone
Metabolite Identification
Common NameParacetamol sulfate
DescriptionParacetamol sulfate is a metabolite of paracetamol, a common drug used for the relief of pain as an antipyretic. After paracetamol is absorbed from the gastrointestinal tract, it forms paracetamol sulphate by conjugation with sulphuric acid. Paracetamol sulfate can be found in both plasma and urine (PMID: 15127815 )
Structure
Thumb
Synonyms
ValueSource
Acetaminophen sulfate esterChEBI
N-(4-(Sulfooxy)phenyl)acetamideChEBI
N-Acetyl-4-aminophenol sulfateChEBI
Acetaminophen sulfuric acid esterGenerator
Acetaminophen sulphate esterGenerator
Acetaminophen sulphuric acid esterGenerator
Acetaminophen sulfuric acidGenerator
Acetaminophen sulphateGenerator
Acetaminophen sulphuric acidGenerator
N-(4-(Sulphooxy)phenyl)acetamideGenerator
N-Acetyl-4-aminophenol sulfuric acidGenerator
N-Acetyl-4-aminophenol sulphateGenerator
N-Acetyl-4-aminophenol sulphuric acidGenerator
(4-Acetamidophenyl) hydrogen sulfateHMDB
(4-Acetamidophenyl) hydrogen sulphateHMDB
4-Acetamidophenyl hydrogen sulfateHMDB
4-Acetamidophenyl hydrogen sulphateHMDB
Chemical FormulaC8H9NO5S
Average Molecular Weight231.226
Monoisotopic Molecular Weight231.020143093
IUPAC Name(4-acetamidophenyl)oxidanesulfonic acid
Traditional Nameacetaminophen sulfate
CAS Registry Number10066-90-7
SMILES
CC(=O)NC1=CC=C(OS(O)(=O)=O)C=C1
InChI Identifier
InChI=1S/C8H9NO5S/c1-6(10)9-7-2-4-8(5-3-7)14-15(11,12)13/h2-5H,1H3,(H,9,10)(H,11,12,13)
InChI KeyInChIKey=IGTYILLPRJOVFY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylsulfates. These are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylsulfates
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • N-arylamide
  • Acetanilide
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Sulfate-ester
  • Acetamide
  • Organic sulfuric acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility1.54 mg/mLALOGPS
logP-1ALOGPS
logP0.43ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-2.2ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.7 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.89 m3·mol-1ChemAxon
Polarizability20.88 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Acetaminophen Metabolism PathwaySMP00640Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineDetected and Quantified138.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00653
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID75741
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB59911
Metagene LinkHMDB59911
METLIN IDNot Available
PubChem Compound83939
PDB IDNot Available
ChEBI ID32635
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen LS, Valentine J, Milne RW, Evans AM: The quantification of paracetamol, paracetamol glucuronide and paracetamol sulphate in plasma and urine using a single high-performance liquid chromatography assay. J Pharm Biomed Anal. 2004 Feb 18;34(3):585-93. [15127815 ]