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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-11 17:54:14 UTC

Update Date

2023-02-21 17:23:12 UTC

HMDB ID

HMDB0033182

Secondary Accession Numbers

HMDB33182

Metabolite Identification

Common Name

2,5-Dimethylfuran

Description

2,5-Dimethylfuran is a derivative of furan. It is a heterocyclic compound of the formula C6H8O. While it may be abbreviated DMF, it should not be confused with dimethylformamide. 2,5-Dimethylfuran is a maillard product. 2,5-Dimethylfuran has been identified as one of the components of cigar smoke with low cilatoxicity (ability to adversely affect the cilia in the respiratory tract that are responsible for removing foreign particles). Its blood concentration can be used as a biomarker for smoking. 2,5-Dimethylfuran, together with 2,5-hexanedione and 4,5-dihydroxy-2-hexanone, is one of the main metabolites of hexane in humans, which play a role in the mechanism for the neurotoxicity of hexane.Recent advances have increased its attractiveness as a biofuel.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,5-Dimethyl-furan	ChEBI
2,5-Dimethylfurane	ChEBI

Chemical Formula

C₆H₈O

Average Molecular Weight

96.1271

Monoisotopic Molecular Weight

96.057514878

IUPAC Name

2,5-dimethylfuran

Traditional Name

2,5-dimethylfuran

CAS Registry Number

625-86-5

SMILES

CC1=CC=C(C)O1

InChI Identifier

InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3

InChI Key

GSNUFIFRDBKVIE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Heteroaromatic compound
Furan
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0033182)
Cytoplasm (HMDB: HMDB0033182)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0033182)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0033182)
Urine (HMDB: HMDB0033182)

Source

Exogenous

Food

Food (HMDB: HMDB0033182)

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033182)

Industrial application

Food and nutrition

Food and nutrition (HMDB: HMDB0033182)

Pharmaceutical industry

Biomarker

2,5-Dimethylfuran Exposure (MarkerDB: MDB00029794)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-63 °C	Not Available
Boiling Point	92.00 to 94.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1466 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.24	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.55 g/L	ALOGPS
logP	2.17	ALOGPS
logP	1.51	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	13.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	28.87 m³·mol⁻¹	ChemAxon
Polarizability	11.09 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	117.721	31661259
DarkChem	[M-H]-	113.979	31661259
DeepCCS	[M+H]+	127.92	30932474
DeepCCS	[M-H]-	125.911	30932474
DeepCCS	[M-2H]-	161.528	30932474
DeepCCS	[M+Na]+	136.183	30932474
AllCCS	[M+H]+	115.3	32859911
AllCCS	[M+H-H2O]+	110.1	32859911
AllCCS	[M+NH4]+	120.2	32859911
AllCCS	[M+Na]+	121.6	32859911
AllCCS	[M-H]-	117.1	32859911
AllCCS	[M+Na-2H]-	120.1	32859911
AllCCS	[M+HCOO]-	123.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dimethylfuran	CC1=CC=C(C)O1	927.5	Standard polar	33892256
2,5-Dimethylfuran	CC1=CC=C(C)O1	714.2	Standard non polar	33892256
2,5-Dimethylfuran	CC1=CC=C(C)O1	700.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylfuran EI-B (Non-derivatized)	splash10-0f6w-9000000000-c4a1e868867e02296ecb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2,5-Dimethylfuran EI-B (Non-derivatized)	splash10-0f6w-9000000000-c4a1e868867e02296ecb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethylfuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-5541d1a8919494d09a97	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dimethylfuran GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-654fd33daad26ad7f6de	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 10V, Positive-QTOF	splash10-0002-9000000000-c1f5eca2bb55a34c6543	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 20V, Positive-QTOF	splash10-0002-9000000000-5506ccbd7d54899cdf5b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 40V, Positive-QTOF	splash10-0udi-9000000000-e12a4cdc311091858f8c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 10V, Negative-QTOF	splash10-0002-9000000000-03aafe04d643341b91c1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 20V, Negative-QTOF	splash10-0002-9000000000-6c128c2cf7b062b9ad93	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 40V, Negative-QTOF	splash10-0ftb-9000000000-efa612ea3a77b76d3d8d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 10V, Positive-QTOF	splash10-0fba-9000000000-c1e51a5940fb21277002	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 20V, Positive-QTOF	splash10-0fba-9000000000-b4e0bd7ed39f1cbf2e1c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 40V, Positive-QTOF	splash10-0ufr-9000000000-df50467e5f4359dae187	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 10V, Negative-QTOF	splash10-004i-9000000000-b50ddc91987bceb8c2b3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 20V, Negative-QTOF	splash10-004i-9000000000-3baf92a782df3868fc98	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dimethylfuran 40V, Negative-QTOF	splash10-0ufv-9000000000-5f4efb78df2931d80f26	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000166 uM	Adult (>18 years old)	Not Specified	Normal	National Health a...	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	19167006	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22284503	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	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
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	22284503	details

Associated Disorders and Diseases

Disease References

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 ]
Perillyl alcohol administration for cancer treatment
Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]

Associated OMIM IDs

266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011193

KNApSAcK ID

Not Available

Chemspider ID

11763

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,5-Dimethylfuran

METLIN ID

Not Available

PubChem Compound

12266

PDB ID

Not Available

ChEBI ID

89052

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029794

Good Scents ID

rw1040081

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2,5-Dimethylfuran (HMDB0033182)

MOL for HMDB0033182 (2,5-Dimethylfuran)

3D MOL for HMDB0033182 (2,5-Dimethylfuran)

3D SDF for HMDB0033182 (2,5-Dimethylfuran)

3D-SDF for HMDB0033182 (2,5-Dimethylfuran)

PDB for HMDB0033182 (2,5-Dimethylfuran)

3D PDB for HMDB0033182 (2,5-Dimethylfuran)

SMILES for HMDB0033182 (2,5-Dimethylfuran)

INCHI for HMDB0033182 (2,5-Dimethylfuran)

Structure for HMDB0033182 (2,5-Dimethylfuran)

3D Structure for HMDB0033182 (2,5-Dimethylfuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra