Showing Compound Card for 1,3,5-Trihydroxybenzene (CDB005040)

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Record Information
Version1.0
Created at2020-04-17 19:03:15 UTC
Updated at2020-11-18 16:39:14 UTC
CannabisDB IDCDB005040
Secondary Accession NumbersNot Available
Cannabis Compound 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. 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. 1,3,5-Trihydroxybenzene has been found to be a metabolite in Pseudomonas (PMID: 15826166 ). 1,3,5-Trihydroxybenzene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,3,5-Trihydroxybenzene is found, on average, in the highest concentration within garden onions. 1,3,5-Trihydroxybenzene has also been detected, but not quantified in, several different foods, such as carobs, highbush blueberries, soft-necked garlics, tarragons, and tea. This could make 1,3,5-trihydroxybenzene a potential biomarker for the consumption of these foods. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional. Phloroglucinol is a benzenetriol. 1,3,5-Trihydroxybenzene is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight126.0317
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS1,3,5-Trihydroxybenzene, non-derivatized, GC-MS Spectrumsplash10-0037-1925000000-c724191b9103115057caSpectrum
GC-MS1,3,5-Trihydroxybenzene, non-derivatized, GC-MS Spectrumsplash10-0037-1925000000-c724191b9103115057caSpectrum
Predicted GC-MS1,3,5-Trihydroxybenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1900000000-dd0ed35d23318896d1b9Spectrum
Predicted GC-MS1,3,5-Trihydroxybenzene, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9266000000-2317d43ce1d2bdb60083Spectrum
Predicted GC-MS1,3,5-Trihydroxybenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1,3,5-Trihydroxybenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-104015e2f367513be83d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000o-9000000000-66ca2cf660ad4426c0212020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-1900000000-d25737e313306ff2b48d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-1900000000-6a0b9a2f7d646e89cea42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-3900000000-d102992a3cf4a244a8c62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-004i-7900000000-e4022d17507410f9dea62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a6r-9500000000-efa09c9675e92917dc712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a4i-9200000000-b8189deed5b441103a172020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9100000000-91c096b5c6bca93fb2012020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9000000000-2dfdf462ad4af57dd4ee2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9000000000-0e5ee4e7603fdee5aa912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0a4i-9000000000-ee965d165837c624e0a42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0a4i-9000000000-42a5aadbd8a2700fcb8a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-0a4i-9000000000-ced455fb5a135cb19c2e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-001i-9000000000-23bf2d29b2666f3f65fa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-004i-0900000000-4e75317d3710eb5b0c502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-004i-0900000000-944db6cc3187837776222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-004i-0900000000-c9f3189fb88bc03828f12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-004i-0900000000-11900ad61e01b6d4449b2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-85c95c94bd781f89f7122016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-75dcf760031bb09416a12016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-8f7164ec36db279bbbbf2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-09436c8cdb204e5cecb42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-46ba64f6b6c946b31aae2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-6900000000-776dffab62c69a4b4b022016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0013675
DrugBank IDDB12944
Phenol Explorer Compound ID658
FoodDB 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
References
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 ]