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Showing metabocard for 1-Isopropyl-2-methylbenzene (HMDB0037050)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 22:17:35 UTC
Update Date2019-07-30 21:50:13 UTC
HMDB IDHMDB0037050
Secondary Accession Numbers
  • HMDB37050
Metabolite Identification
Common Name1-Isopropyl-2-methylbenzene
Description1-Isopropyl-2-methylbenzene, also known as O-cymene or O-cymol, belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. 1-Isopropyl-2-methylbenzene is possibly neutral. Outside of the human body, 1-Isopropyl-2-methylbenzene has been detected, but not quantified in, citrus. This could make 1-isopropyl-2-methylbenzene a potential biomarker for the consumption of these foods. 1-Isopropyl-2-methylbenzene, with regard to humans, has been found to be associated with several diseases such as diarrhoea predominant irritable bowel syndrome, pervasive developmental disorder not otherwise specified, ulcerative colitis, and autism; 1-isopropyl-2-methylbenzene has also been linked to the inborn metabolic disorder celiac disease.
Structure
Data?1563862969
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(1-Methylethyl)-2-methylbenzeneHMDB
1-Methyl,2-N-isopropylbenzeneHMDB
1-Methyl-2-(1-methylethyl)-benzeneHMDB
1-Methyl-2-(1-methylethyl)benzene, 9ciHMDB
1-Methyl-2-isopropylbenzeneHMDB
1-Methyl-2-isopropylbenzolHMDB
2-IsopropyltolueneHMDB
Cymene, orthoHMDB
O-CymeneHMDB
O-CymolHMDB
O-IsopropyltolueneHMDB
O-Mentha-1,3,5-trieneHMDB
Ortho-cymeneHMDB
Ortho-cymolHMDB
Chemical FormulaC10H14
Average Molecular Weight134.2182
Monoisotopic Molecular Weight134.109550448
IUPAC Name1-methyl-2-(propan-2-yl)benzene
Traditional Name1-methyl-2-isopropylbenzene
CAS Registry Number527-84-4
SMILES
CC(C)C1=CC=CC=C1C
InChI Identifier
InChI=1S/C10H14/c1-8(2)10-7-5-4-6-9(10)3/h4-8H,1-3H3
InChI KeyWWRCMNKATXZARA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassCumenes
Direct ParentCumenes
Alternative Parents
Substituents
  • Phenylpropane
  • Cumene
  • Toluene
  • Aromatic hydrocarbon
  • Unsaturated hydrocarbon
  • Hydrocarbon
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-71.54 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.023 mg/mL at 25 °CNot Available
LogP4.38Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP4.11ALOGPS
logP3.73ChemAxon
logS-3.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.29 m³·mol⁻¹ChemAxon
Polarizability16.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000f-4900000000-9e95146a0a21b765a8c3Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000f-4900000000-9e95146a0a21b765a8c3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9800000000-90eced199b00356905aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-6b98b0d90b15565d72aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-88d6444d760c61b2e23aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9500000000-0280fe47fac120092895Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-e9eba9504e8c693c8893Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-d8e1d54b671cb752329cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lu-4900000000-4c3e3b6a13cd7c3016aeSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Children (1-13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal		 details
SalivaDetected but not Quantified Children (1-13 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not Quantified Adult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not Quantified Adult (>18 years old)Both
Diarrhea-predominant IBS		 details
FecesDetected but not Quantified Children (1-13 years old)BothAutism details
FecesDetected but not Quantified Children (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not Quantified Adult (>18 years old)Both
Crohn's disease 		details
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
SalivaDetected but not Quantified Children (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
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
FoodDB IDFDB016032
KNApSAcK IDC00010974
Chemspider ID10253
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10703
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Rzepa J, Wojtal L, Staszek D, Grygierczyk G, Labe K, Hajnos M, Kowalska T, Waksmundzka-Hajnos M: Fingerprint of selected Salvia species by HS-GC-MS analysis of their volatile fraction. J Chromatogr Sci. 2009 Aug;47(7):575-80. [PubMed:19772730 ]
  2. Pertsovskii AL, Stel'makh VA: [Chromatographic determination of orthomenthane hydrocarbons in biological media]. Farmakol Toksikol. 1985 Jan-Feb;48(1):55-6. [PubMed:3979538 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .