Human Metabolome Database: Showing metabocard for 1-Isopropyl-2-methylbenzene (HMDB0037050)

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Record Information

Version

4.0

Status

Detected but not Quantified

Creation Date

2012-09-11 22:17:35 UTC

Update Date

2019-07-30 21:50:13 UTC

HMDB ID

HMDB0037050

Secondary Accession Numbers

HMDB37050

Metabolite Identification

Common Name

1-Isopropyl-2-methylbenzene

Description

1-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(1-Methylethyl)-2-methylbenzene	HMDB
1-Methyl,2-N-isopropylbenzene	HMDB
1-Methyl-2-(1-methylethyl)-benzene	HMDB
1-Methyl-2-(1-methylethyl)benzene, 9ci	HMDB
1-Methyl-2-isopropylbenzene	HMDB
1-Methyl-2-isopropylbenzol	HMDB
2-Isopropyltoluene	HMDB
Cymene, ortho	HMDB
O-Cymene	HMDB
O-Cymol	HMDB
O-Isopropyltoluene	HMDB
O-Mentha-1,3,5-triene	HMDB
Ortho-cymene	HMDB
Ortho-cymol	HMDB

Chemical Formula

C₁₀H₁₄

Average Molecular Weight

134.2182

Monoisotopic Molecular Weight

134.109550448

IUPAC Name

1-methyl-2-(propan-2-yl)benzene

Traditional Name

1-methyl-2-isopropylbenzene

CAS Registry Number

527-84-4

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 Key

WWRCMNKATXZARA-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Cumenes

Direct Parent

Cumenes

Alternative Parents

Substituents

Phenylpropane
Cumene
Toluene
Aromatic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Biofluid and excreta:

Role

Biological role:

Nutrient

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-71.54 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.023 mg/mL at 25 °C	Not Available
LogP	4.38	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	4.11	ALOGPS
logP	3.73	ChemAxon
logS	-3.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.29 m³·mol⁻¹	ChemAxon
Polarizability	16.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000f-4900000000-9e95146a0a21b765a8c3	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-000f-4900000000-9e95146a0a21b765a8c3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-9800000000-90eced199b00356905aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-6b98b0d90b15565d72ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2900000000-88d6444d760c61b2e23a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9500000000-0280fe47fac120092895	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-e9eba9504e8c693c8893	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-d8e1d54b671cb752329c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00lu-4900000000-4c3e3b6a13cd7c3016ae	Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Breath
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Breath	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24086492	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24922509	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24657864	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) non progressor	24922509	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Immunoglobulin A nephropathy (IgAN) progressor	24922509	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Diarrhea-predominant IBS	23516449	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Pervasive Developmental Disorder Not Otherwise Specified	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn's disease	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Celiac disease	24657864	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
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
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
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
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
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
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
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

209850 (Autism)
266600 (Crohn's disease)
212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016032

KNApSAcK ID

C00010974

Chemspider ID

10253

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10703

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Pertsovskii AL, Stel'makh VA: [Chromatographic determination of orthomenthane hydrocarbons in biological media]. Farmakol Toksikol. 1985 Jan-Feb;48(1):55-6. [PubMed:3979538 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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

Structure for HMDB0037050 (1-Isopropyl-2-methylbenzene)