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Showing metabocard for Paracetamol sulfate (HMDB0059911)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2013-03-15 15:57:54 UTC
Update Date2020-02-26 16:25:51 UTC
HMDB IDHMDB0059911
Secondary Accession Numbers
  • HMDB59911
Metabolite Identification
Common NameParacetamol sulfate
DescriptionParacetamol sulfate, also known as paracetamol sulfuric acid or 4-acetaminophen sulfate, is classified as a phenylsulfate. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group. Paracetamol sulfate is considered a slightly soluble (in water), acidic compound. Paracetamol 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 sulfate by conjugation with sulfuric acid. Paracetamol sulfate can be found in both plasma and urine (PMID: 15127815 ).
Structure
Data?1563865990
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-Acetaminophen sulfateChEBI
Acetaminophen sulfateChEBI
Acetaminophen sulfate esterChEBI
N-(4-(Sulfooxy)phenyl)acetamideChEBI
N-Acetyl-4-aminophenol sulfateChEBI
4-Acetaminophen sulfuric acidGenerator
4-Acetaminophen sulphateGenerator
4-Acetaminophen sulphuric acidGenerator
Acetaminophen sulfuric acidGenerator
Acetaminophen sulphateGenerator
Acetaminophen sulphuric acidGenerator
Acetaminophen sulfuric acid esterGenerator
Acetaminophen sulphate esterGenerator
Acetaminophen sulphuric acid esterGenerator
N-(4-(Sulphooxy)phenyl)acetamideGenerator
N-Acetyl-4-aminophenol sulfuric acidGenerator
N-Acetyl-4-aminophenol sulphateGenerator
N-Acetyl-4-aminophenol sulphuric acidGenerator
Paracetamol sulfuric acidGenerator
Paracetamol sulphateGenerator
Paracetamol sulphuric acidGenerator
Acetaminophen sulfate ester, monopotassium saltHMDB
Acetaminophen-sulfateHMDB
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 KeyIGTYILLPRJOVFY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylsulfates. Phenylsulfates are compounds containing a sulfuric acid group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfuric acids and derivatives
Sub ClassArylsulfates
Direct ParentPhenylsulfates
Alternative Parents
Substituents
  • Phenylsulfate
  • Phenoxy compound
  • Monocyclic benzene moiety
  • Sulfuric acid monoester
  • Benzenoid
  • Sulfuric acid ester
  • Sulfate-ester
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.89 m³·mol⁻¹ChemAxon
Polarizability20.88 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052u-1910000000-4ee58d86bf185f461627Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-5bad922abf676bb4b1f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1940000000-7efc6683f5827c5c7a28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hb9-4920000000-f9c40a12b34dc5c8873fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0290000000-32990649c8c1c547530dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgr-0920000000-ed846e515158c2272d36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-2900000000-b2669c115f7c413a29b1Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    		 details
    UrineDetected and Quantified138.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    Associated Disorders and Diseases
    Disease References
    Colorectal cancer
    1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDNot Available
    KNApSAcK IDNot Available
    Chemspider IDNot Available
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound83939
    PDB IDNot Available
    ChEBI ID32635
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    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. [PubMed:15127815 ]
    2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]