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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 05:49:20 UTC
Update Date2020-02-26 21:26:23 UTC
HMDB IDHMDB0006408
Secondary Accession Numbers
  • HMDB0060976
  • HMDB06408
  • HMDB60976
Metabolite Identification
Common Name4-Hydroxy tolbutamide
Description4-Hydroxy tolbutamide belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. 4-Hydroxy tolbutamide is a hydroxylation byproduct of tolbutamide. 4-Hydroxy tolbutamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Tolbutamide is a first generation potassium channel blocker. It is a sulfonylurea oral hypoglycemic drug sold under the brand name Orinase. Tolbutamide stimulates the secretion of insulin by the pancreas.
Structure
Data?1582752383
Synonyms
ValueSource
1-Butyl-3-(4-hydroxymethylphenyl)sulfonylureaChEBI
HydroxymethyltolbutamideChEBI
HydroxytolbutamideChEBI
MethylhydroxytolbutamideChEBI
1-Butyl-3-(4-hydroxymethylphenyl)sulphonylureaGenerator
4 Hydroxy tolbutamideHMDB
4-HydroxytolbutamideHMDB
N-((Butylamino)carbonyl)-4-(hydroxymethyl)benzenesulfonamideHMDB
Chemical FormulaC12H18N2O4S
Average Molecular Weight286.347
Monoisotopic Molecular Weight286.098727764
IUPAC Name3-butyl-1-[4-(hydroxymethyl)benzenesulfonyl]urea
Traditional Namehydroxytolbutamide
CAS Registry Number1185112-19-9
SMILES
CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C1
InChI Identifier
InChI=1S/C12H18N2O4S/c1-2-3-8-13-12(16)14-19(17,18)11-6-4-10(9-15)5-7-11/h4-7,15H,2-3,8-9H2,1H3,(H2,13,14,16)
InChI KeySJRHYONYKZIRPM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Benzyl alcohol
  • Sulfonylurea
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Carbonic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

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 Solubility0.68 g/LALOGPS
logP1.13ALOGPS
logP1.01ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.5 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity72.04 m³·mol⁻¹ChemAxon
Polarizability29.64 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, Positivesplash10-0c00-7980000000-79f53f4297ab2ff88696Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9823000000-8735d28a2bdfb4492da6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ri-6790000000-15179d796c15f8bff29dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-9500000000-211280021c7662da1508Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-9025f9817a60f20e38efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1290000000-4449465e9857aca8ee5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1930000000-d20c0dffd148ceeeb600Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0573-8900000000-d3376933c13afb8faea0Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023913
KNApSAcK IDNot Available
Chemspider ID3529
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2299999
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3656
PDB IDNot Available
ChEBI ID63799
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available