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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-04-03 14:10:30 UTC
Update Date2020-02-26 21:39:02 UTC
HMDB IDHMDB0013675
Secondary Accession Numbers
  • HMDB13675
Metabolite Identification
Common Name1,3,5-Trihydroxybenzene
Description1,3,5-Trihydroxybenzene, also known as 1,3,5-benzenetriol or benzene-1,3,5-triol, belongs to the class of organic compounds known as phloroglucinols and derivatives. Phloroglucinols and derivatives are compounds containing a phloroglucinol (benzene-1,3,5-triol) moiety, which consists of a benzene ring bearing one hydroxyl group at positions 1,3, and 5. 1,3,5-Trihydroxybenzene is found, on average, in the highest concentration within garden onions (Allium cepa). 1,3,5-Trihydroxybenzene has also been detected, but not quantified in, several different foods, such as sweet rowanberries (Grataegosorbus mitschurinii), common wheats (Triticum aestivum), nopals (Opuntia cochenillifera), grapefruits (Citrus X paradisi), and climbing beans (Vigna umbellata). This could make 1,3,5-trihydroxybenzene a potential biomarker for the consumption of these foods. 1,3,5-Trihydroxybenzene is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 1,3,5-Trihydroxybenzene.
Structure
Data?1582753142
Synonyms
ValueSource
1,3,5-BenzenetriolChEBI
Benzene-1,3,5-triolChEBI
S-TrihydroxybenzeneChEBI
Dilospan SKegg
1,3,5-TrihydroxybenzeneChEBI
1,3, 5-TrihydroxybenzeneHMDB
1,3,5-Benzenetriol (acd/name 4.0)HMDB
1,3,5-Trihydroxy-benzeneHMDB
1,3,5-TrihydroxycyclohexatrieneHMDB
1,3,5-TriolHMDB
3,5-DihydroxyphenolHMDB
5-BenzenetriolHMDB
5-HydroxyresorcinolHMDB
5-OxyresorcinolHMDB
5-OxyresorcinolphloroglucinHMDB
Benzene, trihydroxyHMDB
Benzene-S-triolHMDB
FloroglucinHMDB
FloroglucinolHMDB
PhloroglucinHMDB
PhloroglucineHMDB
Phloroglucinol (1,3,5-benzenetriol)HMDB
Spasfon-lyocHMDB, MeSH
Sym-trihydroxybenzeneHMDB
SpassirexMeSH
PhloroglucinolHMDB
Chemical FormulaC6H6O3
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
IUPAC Namebenzene-1,3,5-triol
Traditional Namephloroglucinol
CAS Registry Number108-73-6
SMILES
OC1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
InChI KeyQCDYQQDYXPDABM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phloroglucinols and derivatives. Phloroglucinols and derivatives are compounds containing a phloroglucinol (benzene-1,3,5-triol) moiety, which consists of a benzene ring bearing one hydroxyl group at positions 1,3, and 5.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenetriols and derivatives
Direct ParentPhloroglucinols and derivatives
Alternative Parents
Substituents
  • Phloroglucinol derivative
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.6 mg/mL at 20 °CNot Available
LogP0.16Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility35.8 g/LALOGPS
logP10(0.25) g/LALOGPS
logP10(1.06) g/LChemAxon
logS10(-0.55) g/LALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32 m³·mol⁻¹ChemAxon
Polarizability11.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.87631661259
DarkChem[M-H]-121.6631661259
DeepCCS[M+H]+121.7230932474
DeepCCS[M-H]-117.85130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,3,5-TrihydroxybenzeneOC1=CC(O)=CC(O)=C13538.4Standard polar33892256
1,3,5-TrihydroxybenzeneOC1=CC(O)=CC(O)=C11685.7Standard non polar33892256
1,3,5-TrihydroxybenzeneOC1=CC(O)=CC(O)=C11628.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,3,5-Trihydroxybenzene,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=CC(O)=C11665.0Semi standard non polar33892256
1,3,5-Trihydroxybenzene,2TMS,isomer #1C[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C)=C11636.0Semi standard non polar33892256
1,3,5-Trihydroxybenzene,3TMS,isomer #1C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C11662.1Semi standard non polar33892256
1,3,5-Trihydroxybenzene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O)=C11884.1Semi standard non polar33892256
1,3,5-Trihydroxybenzene,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C12078.6Semi standard non polar33892256
1,3,5-Trihydroxybenzene,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C12286.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1,3,5-Trihydroxybenzene GC-EI-TOF (Non-derivatized)splash10-0037-1925000000-c724191b9103115057ca2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,3,5-Trihydroxybenzene GC-EI-TOF (Non-derivatized)splash10-0037-1925000000-c724191b9103115057ca2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3,5-Trihydroxybenzene GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1900000000-dd0ed35d23318896d1b92017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3,5-Trihydroxybenzene GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9266000000-2317d43ce1d2bdb600832017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3,5-Trihydroxybenzene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,3,5-Trihydroxybenzene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene LC-ESI-QFT , positive-QTOFsplash10-0002-9000000000-104015e2f367513be83d2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene LC-ESI-QTOF 35V, positive-QTOFsplash10-000o-9000000000-66ca2cf660ad4426c0212020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene LC-ESI-QFT , negative-QTOFsplash10-0a4i-1900000000-d25737e313306ff2b48d2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 2V, negative-QTOFsplash10-004i-1900000000-6a0b9a2f7d646e89cea42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 2V, negative-QTOFsplash10-004i-3900000000-d102992a3cf4a244a8c62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 3V, negative-QTOFsplash10-004i-7900000000-e4022d17507410f9dea62020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 4V, negative-QTOFsplash10-0a6r-9500000000-efa09c9675e92917dc712020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 4V, negative-QTOFsplash10-0a4i-9200000000-b8189deed5b441103a172020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 5V, negative-QTOFsplash10-0a4i-9100000000-91c096b5c6bca93fb2012020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 5V, negative-QTOFsplash10-0a4i-9000000000-2dfdf462ad4af57dd4ee2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 6V, negative-QTOFsplash10-0a4i-9000000000-0e5ee4e7603fdee5aa912020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 7V, negative-QTOFsplash10-0a4i-9000000000-ee965d165837c624e0a42020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 8V, negative-QTOFsplash10-0a4i-9000000000-42a5aadbd8a2700fcb8a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene Orbitrap 10V, negative-QTOFsplash10-0a4i-9000000000-ced455fb5a135cb19c2e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene n/a 8V, negative-QTOFsplash10-001i-9000000000-23bf2d29b2666f3f65fa2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene QTOF 3V, positive-QTOFsplash10-004i-0900000000-4e75317d3710eb5b0c502020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene QTOF 4V, positive-QTOFsplash10-004i-0900000000-944db6cc3187837776222020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene QTOF 5V, positive-QTOFsplash10-004i-0900000000-c9f3189fb88bc03828f12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene QTOF 7V, positive-QTOFsplash10-004i-0900000000-11900ad61e01b6d4449b2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene 10V, Positive-QTOFsplash10-004i-0900000000-85c95c94bd781f89f7122016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene 20V, Positive-QTOFsplash10-004i-0900000000-75dcf760031bb09416a12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene 40V, Positive-QTOFsplash10-0a4i-2900000000-8f7164ec36db279bbbbf2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene 10V, Negative-QTOFsplash10-004i-0900000000-09436c8cdb204e5cecb42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene 20V, Negative-QTOFsplash10-004i-0900000000-46ba64f6b6c946b31aae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,3,5-Trihydroxybenzene 40V, Negative-QTOFsplash10-004i-6900000000-776dffab62c69a4b4b022016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12944
Phenol Explorer Compound ID658
FooDB IDFDB013879
KNApSAcK IDC00002665
Chemspider ID352
KEGG Compound IDC02183
BioCyc IDCPD-16
BiGG IDNot Available
Wikipedia LinkPhloroglucinol
METLIN IDNot Available
PubChem Compound359
PDB IDNot Available
ChEBI ID16204
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. Achkar J, Xian M, Zhao H, Frost JW: Biosynthesis of phloroglucinol. J Am Chem Soc. 2005 Apr 20;127(15):5332-3. doi: 10.1021/ja042340g. [PubMed:15826166 ]