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Record Information
Version4.0
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
DescriptionPhloroglucinol is a benzenetriol. It is an organic compound that is used in the synthesis of pharmaceuticals and explosives. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5-cyclohexanetrione (phloroglucin), which has ketone-like character. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional. 1,3,5-Trihydroxybenzene has been found to be a metabolite in Pseudomonas (PMID: 15826166 ).
Structure
Data?1582753142
Synonyms
ValueSource
1,3,5-BenzenetriolChEBI
Benzene-1,3,5-triolChEBI
S-TrihydroxybenzeneChEBI
Dilospan SKegg
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
Sym-trihydroxybenzeneHMDB
1,3,5-TrihydroxybenzeneChEBI
SpassirexMeSH
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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.6 mg/mL at 20 °CNot Available
LogP0.16Not Available
Predicted Properties
PropertyValueSource
Water Solubility35.8 g/LALOGPS
logP0.25ALOGPS
logP1.06ChemAxon
logS-0.55ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0037-1925000000-c724191b9103115057caSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0037-1925000000-c724191b9103115057caSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-1900000000-dd0ed35d23318896d1b9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-9266000000-2317d43ce1d2bdb60083Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-104015e2f367513be83dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000o-9000000000-66ca2cf660ad4426c021Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-1900000000-d25737e313306ff2b48dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-1900000000-6a0b9a2f7d646e89cea4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-3900000000-d102992a3cf4a244a8c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-004i-7900000000-e4022d17507410f9dea6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a6r-9500000000-efa09c9675e92917dc71Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a4i-9200000000-b8189deed5b441103a17Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9100000000-91c096b5c6bca93fb201Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9000000000-2dfdf462ad4af57dd4eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9000000000-0e5ee4e7603fdee5aa91Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0a4i-9000000000-ee965d165837c624e0a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0a4i-9000000000-42a5aadbd8a2700fcb8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-0a4i-9000000000-ced455fb5a135cb19c2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-001i-9000000000-23bf2d29b2666f3f65faSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-004i-0900000000-4e75317d3710eb5b0c50Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-004i-0900000000-944db6cc318783777622Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-004i-0900000000-c9f3189fb88bc03828f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-004i-0900000000-11900ad61e01b6d4449bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-85c95c94bd781f89f712Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-75dcf760031bb09416a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-8f7164ec36db279bbbbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-09436c8cdb204e5cecb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-46ba64f6b6c946b31aaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-6900000000-776dffab62c69a4b4b02Spectrum
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 ID
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 ]