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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-04-03 14:10:30 UTC
Update Date2020-11-09 23:19:06 UTC
HMDB IDHMDB0013674
Secondary Accession Numbers
  • HMDB13674
Metabolite Identification
Common Name1,2,3-Trihydroxybenzene
Description1,2,3-Trihydroxybenzene, also known as pyrogallic acid or 1,2,3-benzenetriol, belongs to the class of organic compounds known as 5-unsubstituted pyrrogallols. These are pyrrogallols that are unsubstituted at th5-position of the benzene ring. 1,2,3-Trihydroxybenzene is found, on average, in the highest concentration within a few different foods, such as robusta coffees (Coffea canephora), coffees (Coffea), and arabica coffees (Coffea arabica) and in a lower concentration in cocoa powder and beer. 1,2,3-Trihydroxybenzene has also been detected, but not quantified in, eggplants (Solanum melongena). This could make 1,2,3-trihydroxybenzene a potential biomarker for the consumption of these foods. 1,2,3-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 1,2,3-Trihydroxybenzene.
Structure
Data?1582753141
Synonyms
ValueSource
1,2,3-BenzenetriolChEBI
Benzene-1,2,3-triolChEBI
Pyrogallic acidChEBI
PyrogallolKegg
PyrogallateGenerator
Acid, pyrogallicMeSH
1,2,3-Benzenetriol (acd/name 4.0)HMDB
1,2,3-Trihydroxy-benzeneHMDB
1,2,3-TrihydroxybenzenHMDB
2,3-DihydroxyphenolHMDB
C.I. oxidation base 32HMDB
Fouramine base apHMDB
Fouramine brown apHMDB
Fourrine 85HMDB
Fourrine PGHMDB
PhenolHMDB
PiralHMDB
PyroHMDB
1,2,3-TrihydroxybenzeneHMDB
Chemical FormulaC6H6O3
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
IUPAC Namebenzene-1,2,3-triol
Traditional Namepyrogallol
CAS Registry Number87-66-1
SMILES
[H]OC1=CC=CC(O[H])=C1O[H]
InChI Identifier
InChI=1S/C6H6O3/c7-4-2-1-3-5(8)6(4)9/h1-3,7-9H
InChI KeyWQGWDDDVZFFDIG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5-unsubstituted pyrrogallols. These are pyrrogallols that are unsubstituted at th5-position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenetriols and derivatives
Direct Parent5-unsubstituted pyrrogallols
Alternative Parents
Substituents
  • 5-unsubstituted pyrrogallol
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility507 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility51.8 g/LALOGPS
logP0.34ALOGPS
logP1.06ChemAxon
logS-0.39ALOGPS
pKa (Strongest Acidic)8.94ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32 m³·mol⁻¹ChemAxon
Polarizability11.57 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]+124.38731661259
DarkChem[M-H]-119.19131661259
DeepCCS[M+H]+128.27930932474
DeepCCS[M-H]-125.2430932474
DeepCCS[M-2H]-162.41630932474
DeepCCS[M+Na]+137.60230932474
AllCCS[M+H]+127.132859911
AllCCS[M+H-H2O]+122.332859911
AllCCS[M+NH4]+131.632859911
AllCCS[M+Na]+132.932859911
AllCCS[M-H]-119.732859911
AllCCS[M+Na-2H]-121.732859911
AllCCS[M+HCOO]-124.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,2,3-Trihydroxybenzene[H]OC1=CC=CC(O[H])=C1O[H]1662.0Standard polar33892256
1,2,3-Trihydroxybenzene[H]OC1=CC=CC(O[H])=C1O[H]973.3Standard non polar33892256
1,2,3-Trihydroxybenzene[H]OC1=CC=CC(O[H])=C1O[H]1111.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,2,3-Trihydroxybenzene,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC(O)=C1O1516.6Semi standard non polar33892256
1,2,3-Trihydroxybenzene,1TMS,isomer #2C[Si](C)(C)OC1=C(O)C=CC=C1O1427.0Semi standard non polar33892256
1,2,3-Trihydroxybenzene,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C)=C1O1479.3Semi standard non polar33892256
1,2,3-Trihydroxybenzene,2TMS,isomer #2C[Si](C)(C)OC1=CC=CC(O)=C1O[Si](C)(C)C1463.2Semi standard non polar33892256
1,2,3-Trihydroxybenzene,3TMS,isomer #1C[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C1541.9Semi standard non polar33892256
1,2,3-Trihydroxybenzene,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC(O)=C1O1743.1Semi standard non polar33892256
1,2,3-Trihydroxybenzene,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O)C=CC=C1O1654.5Semi standard non polar33892256
1,2,3-Trihydroxybenzene,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O1975.6Semi standard non polar33892256
1,2,3-Trihydroxybenzene,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC(O)=C1O[Si](C)(C)C(C)(C)C1959.1Semi standard non polar33892256
1,2,3-Trihydroxybenzene,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2228.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1,2,3-Trihydroxybenzene GC-MS (3 TMS)splash10-000l-3792000000-204d58c54b60969957942014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,2,3-Trihydroxybenzene EI-B (Non-derivatized)splash10-000l-0293000000-317381c3955975af27a62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,2,3-Trihydroxybenzene GC-EI-TOF (Non-derivatized)splash10-000l-1792000000-9b688a43f00234e626d12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,2,3-Trihydroxybenzene GC-MS (Non-derivatized)splash10-000l-3792000000-204d58c54b60969957942017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1,2,3-Trihydroxybenzene GC-EI-TOF (Non-derivatized)splash10-000l-2792000000-8c51cf40229b594f969b2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3-Trihydroxybenzene GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-8900000000-86a07f617d9e8a0401992017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3-Trihydroxybenzene GC-MS (3 TMS) - 70eV, Positivesplash10-00fu-7394000000-523c320e6717d1157dae2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1,2,3-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 - 1,2,3-Trihydroxybenzene 35V, Negative-QTOFsplash10-004i-3900000000-aeb92cf5a0c6ea14fff22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 40V, Positive-QTOFsplash10-0ue9-9000000000-7699321c8f67f04102232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 20V, Positive-QTOFsplash10-001i-9100000000-ea01e7e29e972e1d72462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 10V, Positive-QTOFsplash10-0a4i-2900000000-e697ce0798ac1b834e4c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 20V, Negative-QTOFsplash10-004i-9400000000-44dd7b530071c9df93f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 10V, Negative-QTOFsplash10-004i-2900000000-bb91257afdfff20901ae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 40V, Negative-QTOFsplash10-102c-9100000000-c0e14c51a15ee2e09b242021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 10V, Positive-QTOFsplash10-004i-0900000000-912d8a287d687cb0d66c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 20V, Positive-QTOFsplash10-004i-2900000000-e3d143390169f9266a862016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 40V, Positive-QTOFsplash10-014i-9100000000-8d1d0e03dd45599fc9c02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 10V, Negative-QTOFsplash10-004i-0900000000-ea97e3db0a8790646d2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 20V, Negative-QTOFsplash10-004i-1900000000-b3160bcc0b389cf211d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 40V, Negative-QTOFsplash10-016v-9300000000-bc0f8f26aacd70e402fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 10V, Positive-QTOFsplash10-0a6r-2900000000-4e851cb501d3e45affc92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 20V, Positive-QTOFsplash10-001i-9100000000-3358a867a0e9fb9492b92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 40V, Positive-QTOFsplash10-0udr-9000000000-b92ddc7dd0d4d7cf80812021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 10V, Negative-QTOFsplash10-004i-0900000000-5fac22aad109814b92dd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 20V, Negative-QTOFsplash10-016r-9200000000-8a4799a05e6d74dbb2cd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1,2,3-Trihydroxybenzene 40V, Negative-QTOFsplash10-014l-9000000000-1afa6f5c853d02418a3a2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
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
UrineDetected and Quantified0.07 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID655
FooDB IDFDB008735
KNApSAcK IDC00002670
Chemspider ID13835557
KEGG Compound IDC01108
BioCyc IDPYROGALLOL
BiGG IDNot Available
Wikipedia LinkPyrogallol
METLIN IDNot Available
PubChem Compound1057
PDB IDNot Available
ChEBI ID16164
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 ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
1,2,3-Trihydroxybenzene → 6-(2,3-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
1,2,3-Trihydroxybenzene → 6-(2,6-dihydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails