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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 23:50:45 UTC
Update Date2022-03-07 02:55:48 UTC
HMDB IDHMDB0038524
Secondary Accession Numbers
  • HMDB38524
Metabolite Identification
Common Name5-Tricosyl-1,3-benzenediol
Description5-Tricosyl-1,3-benzenediol, also known as 1,3-dihydroxy-5-tricosylbenzene or 5-N-tricosylresorcinol, belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 5-Tricosyl-1,3-benzenediol is found, on average, in the highest concentration within a few different foods, such as breakfast cereal, rye bread, and hard wheats (Triticum durum) and in a lower concentration in common wheats (Triticum aestivum), barleys (Hordeum vulgare), and pasta. 5-Tricosyl-1,3-benzenediol has also been detected, but not quantified in, several different foods, such as cereals and cereal products, wheats (Triticum), annual wild rice (Zizania aquatica), spelts (Triticum spelta), and soy beans (Glycine max). This could make 5-tricosyl-1,3-benzenediol a potential biomarker for the consumption of these foods. 5-Tricosyl-1,3-benzenediol 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 a significant number of articles have been published on 5-Tricosyl-1,3-benzenediol.
Structure
Data?1563863211
Synonyms
ValueSource
1,3-Dihydroxy-5-N-tricosylbenzeneChEBI
1,3-Dihydroxy-5-tricosylbenzeneChEBI
5-N-TricosylresorcinolChEBI
5-TricosylresorcinolHMDB
Chemical FormulaC29H52O2
Average Molecular Weight432.722
Monoisotopic Molecular Weight432.396730908
IUPAC Name5-tricosylbenzene-1,3-diol
Traditional Name5-tricosylbenzene-1,3-diol
CAS Registry Number70110-60-0
SMILES
CCCCCCCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C29H52O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-24-28(30)26-29(31)25-27/h24-26,30-31H,2-23H2,1H3
InChI KeyOHTBGMREZYLZQD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentResorcinols
Alternative Parents
Substituents
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
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 Solubility3.4e-05 g/LALOGPS
logP10.15ALOGPS
logP11.66ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)9.36ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity136.28 m³·mol⁻¹ChemAxon
Polarizability59.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+216.38131661259
DarkChem[M-H]-217.02331661259
DeepCCS[M+H]+218.83430932474
DeepCCS[M-H]-216.28430932474
DeepCCS[M-2H]-249.48730932474
DeepCCS[M+Na]+225.82130932474
AllCCS[M+H]+227.032859911
AllCCS[M+H-H2O]+225.132859911
AllCCS[M+NH4]+228.932859911
AllCCS[M+Na]+229.432859911
AllCCS[M-H]-215.532859911
AllCCS[M+Na-2H]-219.132859911
AllCCS[M+HCOO]-223.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Tricosyl-1,3-benzenediolCCCCCCCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C14400.1Standard polar33892256
5-Tricosyl-1,3-benzenediolCCCCCCCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C13531.0Standard non polar33892256
5-Tricosyl-1,3-benzenediolCCCCCCCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C13688.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Tricosyl-1,3-benzenediol,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O[Si](C)(C)C)=C13537.1Semi standard non polar33892256
5-Tricosyl-1,3-benzenediol,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C13527.9Semi standard non polar33892256
5-Tricosyl-1,3-benzenediol,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C13784.3Semi standard non polar33892256
5-Tricosyl-1,3-benzenediol,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCCCCC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C14025.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Tricosyl-1,3-benzenediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-3960000000-607d4efd2520776db8472017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Tricosyl-1,3-benzenediol GC-MS (2 TMS) - 70eV, Positivesplash10-03k9-9580030000-3b055628038b70b0266e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Tricosyl-1,3-benzenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Tricosyl-1,3-benzenediol 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 - 5-Tricosyl-1,3-benzenediol 10V, Positive-QTOFsplash10-001i-0011900000-d0e9fdff29d0239e66962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 20V, Positive-QTOFsplash10-053r-1598300000-f161b7f27a984ded5bee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 40V, Positive-QTOFsplash10-052f-5696000000-6488543f72f8364dbcc82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 10V, Negative-QTOFsplash10-001i-0000900000-da51a0e14f537c9115f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 20V, Negative-QTOFsplash10-001i-0000900000-ae0f462b63285df7fbdd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 40V, Negative-QTOFsplash10-05n0-1569400000-77c3fff44d1cf67df7942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 10V, Negative-QTOFsplash10-001i-0000900000-7334716c64d1f81101b72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 20V, Negative-QTOFsplash10-001i-0000900000-9c3755787761c430a9772021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 40V, Negative-QTOFsplash10-00dr-3903200000-a1387f18c64e549b046d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 10V, Positive-QTOFsplash10-001i-1002900000-93bd9c309aa3710c0af62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 20V, Positive-QTOFsplash10-00lr-9417800000-ae2c5c8bba770a83b7d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Tricosyl-1,3-benzenediol 40V, Positive-QTOFsplash10-052f-9201000000-4ab76a536966becdd8fe2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0117 +/- 0.00650 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.00626 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00645 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0103 +/- 0.00460 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.007 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.011 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.013 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0113 +/- 0.00600 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID699
FooDB IDFDB017907
KNApSAcK IDNot Available
Chemspider ID136953
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound155462
PDB IDNot Available
ChEBI ID145969
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .