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Record Information
Version5.0
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 secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 4-Hydroxy tolbutamide.
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)benzenesulfonamideMeSH, HMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.4631661259
DarkChem[M-H]-166.70331661259
DeepCCS[M+H]+169.38730932474
DeepCCS[M-H]-167.02930932474
DeepCCS[M-2H]-199.91530932474
DeepCCS[M+Na]+175.4830932474
AllCCS[M+H]+164.132859911
AllCCS[M+H-H2O]+160.932859911
AllCCS[M+NH4]+167.032859911
AllCCS[M+Na]+167.932859911
AllCCS[M-H]-164.032859911
AllCCS[M+Na-2H]-164.532859911
AllCCS[M+HCOO]-165.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy tolbutamideCCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C14211.6Standard polar33892256
4-Hydroxy tolbutamideCCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C11782.9Standard non polar33892256
4-Hydroxy tolbutamideCCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C12564.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy tolbutamide,1TMS,isomer #1CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C12638.5Semi standard non polar33892256
4-Hydroxy tolbutamide,1TMS,isomer #2CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C2518.8Semi standard non polar33892256
4-Hydroxy tolbutamide,1TMS,isomer #3CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C12501.4Semi standard non polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #1CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C2544.1Semi standard non polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #1CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C2584.5Standard non polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #1CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C3190.5Standard polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #2CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C12548.1Semi standard non polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #2CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C12474.1Standard non polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #2CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C13303.3Standard polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #3CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C2437.0Semi standard non polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #3CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C2648.0Standard non polar33892256
4-Hydroxy tolbutamide,2TMS,isomer #3CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C3245.3Standard polar33892256
4-Hydroxy tolbutamide,3TMS,isomer #1CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C2480.4Semi standard non polar33892256
4-Hydroxy tolbutamide,3TMS,isomer #1CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C2711.4Standard non polar33892256
4-Hydroxy tolbutamide,3TMS,isomer #1CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C2985.8Standard polar33892256
4-Hydroxy tolbutamide,1TBDMS,isomer #1CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C12879.5Semi standard non polar33892256
4-Hydroxy tolbutamide,1TBDMS,isomer #2CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C(C)(C)C2761.1Semi standard non polar33892256
4-Hydroxy tolbutamide,1TBDMS,isomer #3CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C12782.0Semi standard non polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #1CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3000.4Semi standard non polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #1CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2994.0Standard non polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #1CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3278.8Standard polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #2CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C13054.8Semi standard non polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #2CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C12896.7Standard non polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #2CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C13374.9Standard polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #3CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C(C)(C)C2976.9Semi standard non polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #3CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C(C)(C)C3098.2Standard non polar33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #3CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C(C)(C)C3314.3Standard polar33892256
4-Hydroxy tolbutamide,3TBDMS,isomer #1CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3229.9Semi standard non polar33892256
4-Hydroxy tolbutamide,3TBDMS,isomer #1CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3342.4Standard non polar33892256
4-Hydroxy tolbutamide,3TBDMS,isomer #1CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3170.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy tolbutamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c00-7980000000-79f53f4297ab2ff886962017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy tolbutamide GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9823000000-8735d28a2bdfb4492da62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy tolbutamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy tolbutamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 10V, Positive-QTOFsplash10-00ri-6790000000-15179d796c15f8bff29d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 20V, Positive-QTOFsplash10-05g0-9500000000-211280021c7662da15082016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 40V, Positive-QTOFsplash10-0a4i-9100000000-9025f9817a60f20e38ef2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 10V, Negative-QTOFsplash10-000i-1290000000-4449465e9857aca8ee5f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 20V, Negative-QTOFsplash10-052r-1930000000-d20c0dffd148ceeeb6002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 40V, Negative-QTOFsplash10-0573-8900000000-d3376933c13afb8faea02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 10V, Negative-QTOFsplash10-000i-0930000000-af56d043bc014bed1adc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 20V, Negative-QTOFsplash10-000i-1900000000-f59e8d27a50f370ff6a92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 40V, Negative-QTOFsplash10-004i-9300000000-b6b22115bf1475d3d9352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 10V, Positive-QTOFsplash10-000i-3940000000-12a4c46026f2e5b3ba5f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 20V, Positive-QTOFsplash10-0ab9-3900000000-e692b3121c16132704a92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 40V, Positive-QTOFsplash10-0abc-9700000000-c7adc54472f91da241bd2021-09-25Wishart LabView Spectrum
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 ID4MTOLBUTAMIDE
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available