Np mrd loader

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Record Information
Version1.0
Created at2009-01-30 15:08:14 UTC
Updated at2021-06-30 02:06:20 UTC
NP-MRD IDNP0001479
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Cresol sulfate
DescriptionP-Cresol sulfate is a microbial metabolite that is found in urine and likely derives from secondary metabolism of p-cresol. It appears to be elevated in the urine of individuals with progressive multiple sclerosis (PMID:10775436 ). P-Cresol sulfate is the major component of urinary MBPLM (myelin basic protein-like material). P-Cresol sulfate is a small protein-bound molecule that is poorly cleared with dialysis. It has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821 ). Uremic toxins include other low-molecular-weight compounds such as indoxyl sulfate, 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid, and asymmetric dimethylarginine (PMID:18941347 ). It has also been linked to cardiovascular disease and oxidative injury. Higher levels are associated with overgrowth of intestinal bacteria from Clostridia species, including C. Difficile. P-Cresol is generated by the partial breakdown of tyrosine and phenylalanine by a wide range of intestinal obligate or facultative anaerobes, including the genera Bacteroides, Lactobacillus, Enterobacter, Bifidobacterium, and especially Clostridium (PMID:2394806 ).
Structure
Thumb
Synonyms
ValueSource
4-Cresol sulfateChEBI
Sulfuric acid mono-p-tolyl esterChEBI
4-Cresol sulfuric acidGenerator
4-Cresol sulphateGenerator
4-Cresol sulphuric acidGenerator
Sulfate mono-p-tolyl esterGenerator
Sulphate mono-p-tolyl esterGenerator
Sulphuric acid mono-p-tolyl esterGenerator
p-Cresol sulfuric acidGenerator
p-Cresol sulphateGenerator
p-Cresol sulphuric acidGenerator
mono(4-Methylphenyl) sulfateHMDB
p-Cresyl sulfateHMDB
p-Cresyl sulphateHMDB
p-Cresyl-sulfateHMDB
p-Cresyl-sulphateHMDB
p-CresylsulfateHMDB
p-CresylsulphateHMDB
p-Tolyl sulfate (6ci,7ci)HMDB
p-Tolyl sulphate (6ci,7ci)HMDB
Para-cresol sulfateHMDB
Para-cresol sulphateHMDB
Sulfuric acid mono(p-tolyl) ester (8ci)HMDB
Sulfuric acid, mono(4-methylphenyl) esterHMDB
Chemical FormulaC7H8O4S
Average Mass188.2010 Da
Monoisotopic Mass188.01433 Da
IUPAC Name(4-methylphenyl)oxidanesulfonic acid
Traditional Name(4-methylphenyl)oxidanesulfonic acid
CAS Registry Number3233-58-7
SMILES
CC1=CC=C(OS(O)(=O)=O)C=C1
InChI Identifier
InChI=1S/C7H8O4S/c1-6-2-4-7(5-3-6)11-12(8,9)10/h2-5H,1H3,(H,8,9,10)
InChI KeyWGNAKZGUSRVWRH-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-13View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-13View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Varshavi.d262021-08-17View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)V.dorna832021-08-13View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)V.dorna832021-08-13View Spectrum
Species
Species of Origin
  • Animalia
  • Eubacteria
  • Species Where Detected
    Species NameSourceReference
    Homo sapiens (Urine)KNApSAcK Database
    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
    • Toluene
    • Benzenoid
    • Sulfuric acid ester
    • Sulfate-ester
    • Sulfuric acid monoester
    • Monocyclic benzene moiety
    • Organic oxygen compound
    • Organic oxide
    • Hydrocarbon derivative
    • Organooxygen compound
    • Aromatic homomonocyclic compound
    Molecular FrameworkAromatic homomonocyclic compounds
    External Descriptors
    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 Solubility1.58 g/LALOGPS
    logP10(-0.55) g/LALOGPS
    logP10(1.71) g/LChemAxon
    logS10(-2.1) g/LALOGPS
    pKa (Strongest Acidic)-2ChemAxon
    Physiological Charge-1ChemAxon
    Hydrogen Acceptor Count3ChemAxon
    Hydrogen Donor Count1ChemAxon
    Polar Surface Area63.6 ŲChemAxon
    Rotatable Bond Count2ChemAxon
    Refractivity43.07 m³·mol⁻¹ChemAxon
    Polarizability17.17 ųChemAxon
    Number of Rings1ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterYesChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    HMDB IDHMDB0011635
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB028333
    KNApSAcK IDC00052378
    Chemspider ID3806481
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound4615423
    PDB IDNot Available
    ChEBI ID82914
    Good Scents IDNot Available
    References
    General References
    1. Cao L, Kirk MC, Coward LU, Jackson P, Whitaker JN: p-Cresol sulfate is the dominant component of urinary myelin basic protein like material. Arch Biochem Biophys. 2000 May 1;377(1):9-21. [PubMed:10775436 ]
    2. Raff AC, Meyer TW, Hostetter TH: New insights into uremic toxicity. Curr Opin Nephrol Hypertens. 2008 Nov;17(6):560-5. doi: 10.1097/MNH.0b013e32830f45b6. [PubMed:18941347 ]
    3. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
    4. 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 ]
    5. Sivsammye G, Sims HV: Presumptive identification of Clostridium difficile by detection of p-cresol in prepared peptone yeast glucose broth supplemented with p-hydroxyphenylacetic acid. J Clin Microbiol. 1990 Aug;28(8):1851-3. doi: 10.1128/jcm.28.8.1851-1853.1990. [PubMed:2394806 ]