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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-07 21:35:46 UTC
Update Date2019-07-31 22:49:52 UTC
HMDB IDHMDB0059901
Secondary Accession Numbers
  • HMDB59901
Metabolite Identification
Common NameHemimellitene
DescriptionHemimellitene, also known as hemellitol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Hemimellitene is possibly neutral. Outside of the human body, Hemimellitene is found, on average, in the highest concentration within black walnuts. Hemimellitene has also been detected, but not quantified in, corns and sweet cherries. This could make hemimellitene a potential biomarker for the consumption of these foods. Hemimellitene, with regard to humans, has been found to be associated with several diseases such as asthma and ulcerative colitis; hemimellitene has also been linked to the inborn metabolic disorder celiac disease. These are compounds containing a benzene ring which bears a methane group.
Structure
Data?1563865989
Synonyms
ValueSource
HemellitolChEBI
HemimellitolChEBI
HemimelliteneChEBI
Chemical FormulaC9H12
Average Molecular Weight120.1916
Monoisotopic Molecular Weight120.093900384
IUPAC Name1,2,3-trimethylbenzene
Traditional Name1,2,3-trimethylbenzene
CAS Registry NumberNot Available
SMILES
CC1=CC=CC(C)=C1C
InChI Identifier
InChI=1S/C9H12/c1-7-5-4-6-8(2)9(7)3/h4-6H,1-3H3
InChI KeyFYGHSUNMUKGBRK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

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 Solubility0.079 g/LALOGPS
logP10(3.63) g/LALOGPS
logP10(3.51) g/LChemAxon
logS10(-3.2) g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.18 m³·mol⁻¹ChemAxon
Polarizability14.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.63531661259
DarkChem[M-H]-121.37431661259
DeepCCS[M+H]+128.32830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HemimelliteneCC1=CC=CC(C)=C1C1316.6Standard polar33892256
HemimelliteneCC1=CC=CC(C)=C1C997.9Standard non polar33892256
HemimelliteneCC1=CC=CC(C)=C1C1012.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Hemimellitene EI-B (Non-derivatized)splash10-0ab9-0900000000-efe82e901f88e23974872017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene CI-B (Non-derivatized)splash10-00di-0900000000-40ecbbb508b8b022f78d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene EI-B (Non-derivatized)splash10-0a4i-4900000000-82bebdcf0868386b88db2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene EI-B (Non-derivatized)splash10-0ab9-2900000000-4249969893bf07e58bb12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene CI-B (Non-derivatized)splash10-00di-0900000000-9945be0d63dac31433582017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene EI-B (Non-derivatized)splash10-0ab9-0900000000-efe82e901f88e23974872018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene CI-B (Non-derivatized)splash10-00di-0900000000-40ecbbb508b8b022f78d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene EI-B (Non-derivatized)splash10-0a4i-4900000000-82bebdcf0868386b88db2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene EI-B (Non-derivatized)splash10-0ab9-2900000000-4249969893bf07e58bb12018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Hemimellitene CI-B (Non-derivatized)splash10-00di-0900000000-9945be0d63dac31433582018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hemimellitene GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6900000000-7497a8f53897f14cd3f62016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hemimellitene 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 - Hemimellitene 10V, Positive-QTOFsplash10-00di-0900000000-84665ad8e417cd5c3c6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 20V, Positive-QTOFsplash10-00di-1900000000-f3b880efa2d189ad22df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 40V, Positive-QTOFsplash10-0zmi-9300000000-4526785e0974887f23312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 10V, Negative-QTOFsplash10-014i-0900000000-364d74a767355bac422b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 20V, Negative-QTOFsplash10-014i-0900000000-bad80091043871bb47022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 40V, Negative-QTOFsplash10-014i-4900000000-96ca2cd3fe1b04e09ac52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 10V, Positive-QTOFsplash10-00di-1900000000-44355cb462a3161d65f42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 20V, Positive-QTOFsplash10-00mo-9100000000-831e64ea6dad6547ba642021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 40V, Positive-QTOFsplash10-004i-9100000000-de92d53aa816f86a5d802021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 10V, Negative-QTOFsplash10-014i-0900000000-794ffb5dd5f7d8f3ef502021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 20V, Negative-QTOFsplash10-014i-0900000000-9a88b994768feba6ee262021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hemimellitene 40V, Negative-QTOFsplash10-014i-1900000000-47acabbb26bb09a36a262021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Asthma
  1. van de Kant KD, van Berkel JJ, Jobsis Q, Lima Passos V, Klaassen EM, van der Sande L, van Schayck OC, de Jongste JC, van Schooten FJ, Derks E, Dompeling E, Dallinga JW: Exhaled breath profiling in diagnosing wheezy preschool children. Eur Respir J. 2013 Jan;41(1):183-8. doi: 10.1183/09031936.00122411. [PubMed:23277518 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005814
KNApSAcK IDNot Available
Chemspider ID10236
KEGG Compound IDC14518
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,2,3-Trimethylbenzene
METLIN IDNot Available
PubChem Compound10686
PDB IDNot Available
ChEBI ID34037
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. Wiaderna D, Gralewicz S, Tomas T: Behavioural changes following a four-week inhalation exposure to hemimellitene (1,2,3-trimethylbenzene) in rats. Int J Occup Med Environ Health. 1998;11(4):319-34. [PubMed:10028199 ]
  2. Tsujimoto Y, Noda T, Shimizu M, Moriwaki H, Tanaka M: Identification of the dimethylbenzyl mercapturic acid in urine of rats treated with 1,2,3-trimethylbenzene. Chemosphere. 1999 Aug;39(5):725-30. [PubMed:10448551 ]
  3. Korsak Z, Stetkiewicz J, Majcherek W, Stetkiewicz I, Jajte J, Rydzynski K: Subchronic inhalation toxicity of 1,2,3-trimethylbenzene (hemimellitene) in rats. Int J Occup Med Environ Health. 2000;13(3):223-32. [PubMed:11109746 ]