Showing metabocard for 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate (BMDB0096166)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-10 17:02:17 UTC
Update Date2020-04-22 18:56:28 UTC
BMDB IDBMDB0096166
Secondary Accession Numbers
  • BMDB96166
Metabolite Identification
Common Name3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate
Description3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Elevated levels of HPHPA have been reported in the urine of children with autism as well as in adult patients with schizophrenia. Recently it has been reported that HPHPA is actually an abnormal phenylalanine metabolite arising from bacterial metabolism in the gastrointestinal tract. 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate is an extremely weak basic (essentially neutral) compound (based on its pKa). It has been proposed that HPHPA may be a bacterial metabolite of m-tyrosine, a tyrosine analog that causes symptoms of autism in experimental animals. However, there has been a considerable degree of ambiguity in the origin and/or significance of this compound (PMID:11978597 ). 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphate is the conjugate of 3-hydroxy-3-(3-hydroxyphenyl)propanoic acid and sulphate. It is thought that the presence of this acid is from nutritional sources (i.e. dietary phenylalanine). Specifically HPHPA appears to arise from the action of the anaerobic bacteria Clostrida sp.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Hydroxy-3-(3-hydroxyphenyl)propanoate-O-sulfateGenerator
3-Hydroxy-3-(3-hydroxyphenyl)propanoate-O-sulphateGenerator
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulfuric acidGenerator
3-Hydroxy-3-(3-hydroxyphenyl)propanoic acid-O-sulphuric acidGenerator
SulfO 3-hydroxy-3-(3-hydroxyphenyl)propanoic acidGenerator
SulphO 3-hydroxy-3-(3-hydroxyphenyl)propanoateGenerator
SulphO 3-hydroxy-3-(3-hydroxyphenyl)propanoic acidGenerator
Chemical FormulaC9H10O7S
Average Molecular Weight262.237
Monoisotopic Molecular Weight262.014723364
IUPAC Namesulfo 3-hydroxy-3-(3-hydroxyphenyl)propanoate
Traditional Namesulfo 3-hydroxy-3-(3-hydroxyphenyl)propanoate
CAS Registry NumberNot Available
SMILES
OC(CC(=O)OS(O)(=O)=O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C9H10O7S/c10-7-3-1-2-6(4-7)8(11)5-9(12)16-17(13,14)15/h1-4,8,10-11H,5H2,(H,13,14,15)
InChI KeyMDWXOTLIYUYWJP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfuric acid ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Carboxylic acid salt
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic salt
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.95ALOGPS
logP-1.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)-2.1ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity55.59 m³·mol⁻¹ChemAxon
Polarizability22.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6910000000-6726ada2cb27b9a9ed5eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014j-6389000000-69e59de0ac7859b46e30View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0590000000-7d7d3a0d10ecbf6a581fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2930000000-5de28124a2fa6fdad35cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-4900000000-8d1c25738ded9744f8b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1390000000-52d3ff69936fbe013d09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03du-3920000000-451facc51d79d3fa3f3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-9400000000-3f512cd6df10fe81bb78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0950000000-97aa03a9cc9409dbd665View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2900000000-9fb66e55bb9f0f4cf937View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-9500000000-85ab58495191d2d9cc6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-675e07719da12f0149ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9100000000-ca236561b1d65d853c46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-6ac09489e16983d8b680View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0059967
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 Compound124202083
PDB IDNot Available
ChEBI ID88716
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available