MiMeDB: Showing metabocard for 2,5-Dimethylfuran (MMDBc0007482)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 00:39:27 UTC

Update Date

2024-09-29 14:08:24 UTC

Metabolite ID

MMDBc0007482

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

Synonyms

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

Molecular Formula

C₆H₈O

Average Mass

96.1271

Monoisotopic Mass

96.057514878

IUPAC Name

2,5-dimethylfuran

Traditional Name

2,5-dimethylfuran

CAS Registry Number

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f6w-9000000000-c4a1e868867e02296ecb	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f6w-9000000000-c4a1e868867e02296ecb	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-5541d1a8919494d09a97	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-c1f5eca2bb55a34c6543	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-5506ccbd7d54899cdf5b	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-e12a4cdc311091858f8c	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-03aafe04d643341b91c1	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-6c128c2cf7b062b9ad93	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ftb-9000000000-efa612ea3a77b76d3d8d	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fba-9000000000-c1e51a5940fb21277002	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fba-9000000000-b4e0bd7ed39f1cbf2e1c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-9000000000-df50467e5f4359dae187	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-b50ddc91987bceb8c2b3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-3baf92a782df3868fc98	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ufv-9000000000-5f4efb78df2931d80f26	2021-09-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-654fd33daad26ad7f6de	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, experimental)		2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Metabolic reconstruction; Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Oil	Allium cepa	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Blood	Detected and Quantified	0.000166			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2013
Human Blood	Detected and Quantified		0.0013	0.0017	uM	Not Specified	Both	2,5-Dimethylfuran Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Blood	Detected and Quantified		0.0013	0.0017	uM	Not Specified	Both	2,5-Dimethylfuran Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Blood	Detected and Quantified		0.0012	0.0018	uM	Not Specified	Both	2,5-Dimethylfuran Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	22284503
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	19167006
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	24811995

External Links

HMDB ID

HMDB0033182

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

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 2,5-Dimethylfuran (MMDBc0007482)

MOL for #<Metabolite:0x00007f47056b22b0>

3D MOL for #<Metabolite:0x00007f47056b22b0>

3D SDF for #<Metabolite:0x00007f47056b22b0>

3D-SDF for #<Metabolite:0x00007f47056b22b0>

PDB for #<Metabolite:0x00007f47056b22b0>

3D PDB for #<Metabolite:0x00007f47056b22b0>

SMILES for #<Metabolite:0x00007f47056b22b0>

INCHI for #<Metabolite:0x00007f47056b22b0>

Structure for #<Metabolite:0x00007f47056b22b0>

3D Structure for #<Metabolite:0x00007f47056b22b0>