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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-05-18 14:35:56 UTC

Update Date

2023-02-21 17:18:03 UTC

HMDB ID

HMDB0013785

Secondary Accession Numbers

HMDB13785

Metabolite Identification

Common Name

Furan

Description

Furan is a member of the class of compounds known as furans. These are molecules containing a heterocyclic organic group consisting of a five-membered aromatic ring with four carbon atoms and one oxygen. Furan is aromatic because one of the lone pairs of electrons on the oxygen atom is delocalized into the ring, creating a 4n+2 aromatic system similar to benzene. Because of the aromaticity, furan is flat and lacks discrete double bonds. Furan is a colourless, flammable, highly volatile liquid with a boiling point close to room temperature (31 °C). It is soluble in common organic solvents, including alcohol, ether, and acetone, but is insoluble in water. It has a strong ethereal odour. Furan is found in heat-treated (e.g. cooked, roasted, baked, pasteurized, and sterilized) commercial foods and is produced through thermal degradation of natural food constituents (PMID:22641279 ). It can be found in roasted coffee, instant coffee, and processed baby foods (PMID:22641279 ). In particular, the highest furan levels can be detected in coffee, with mean values between 42 and 3 660 ng/g for brewed coffee and roasted coffee beans. Furan can also be detected at levels between 0.2 and 3.2 ng/g in infant formula, from 22 to 24 ng/g in baked beans, from 13 to 17 ng/g in meat products, and from 23 to 24 ng/g in soups. In soy sauce, furan is detectable at 27 ng/g (PMID:26483883 ). Research has indicated that coffee made in espresso makers and, above all, coffee made from capsules, contains more furan than that made in traditional drip coffee makers, although the levels are still within safe health limits. Various pathways have been reported for the formation of furan: (1) thermal degradation and/or thermal rearrangement of carbohydrates in the presence of amino acids, (2) thermal degradation of certain amino acids (aspartic acid, threonine, alpha-alanine, serine, and cysteine), (3) oxidation of ascorbic acid at higher temperatures, and (4) oxidation of polyunsaturated fatty acids and carotenoids (PMID:26483883 ). Several studies have reported that furan formation occurs to a large extent during the Maillard reaction. The Maillard reaction involves the thermal degradation and rearrangement of carbohydrates (i.e. non-enzymatic browning reactions during food processing and cooking). Reducing hexoses often go through the Maillard reaction in the presence of amino acids and produce reactive intermediates such as 1-deoxy- and 3-deoxyosones, aldotetrose, and 2-deoxy-3-keto-aldotetrose. 2-Deoxy-3-keto-aldotetrose typically goes through retro-aldol cleavage leading to 3-deoxyosone which undergoes alpha-dicarbonyl cleavage, followed by oxidation and decarboxylation to form 2-deoxyaldotetrose, which is a direct precursor of furan. In addition to the formation of furan via carbohydrate degradation, furan can also be formed through thermal degradation of certain amino acids. Specifically, the amino acids that can form acetaldehyde and glycolaldehyde can produce furan by aldol condensation and cyclization (PMID:26483883 ). Furan is toxic and may be carcinogenic. In particular, furan is a potent hepatotoxin and hepatocarcinogen in rodents, causing hepatocellular adenomas and carcinomas in rats and mice, and high incidences of cholangiocarcinomas in rats at doses ≥ 2 mg/kg (PMID:22641279 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,4-Epoxy-1,3-butadiene	ChEBI
Divinylene oxide	ChEBI
Furane	ChEBI
Oxacyclopentadiene	ChEBI
Oxole	ChEBI
Tetrole	ChEBI
Furfuran	HMDB
Furfurane	HMDB

Chemical Formula

C₄H₄O

Average Molecular Weight

68.074

Monoisotopic Molecular Weight

68.02621475

IUPAC Name

furan

Traditional Name

furan

CAS Registry Number

110-00-9

SMILES

O1C=CC=C1

InChI Identifier

InChI=1S/C4H4O/c1-2-4-5-3-1/h1-4H

InChI Key

YLQBMQCUIZJEEH-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

furans (CHEBI:35559 )
mancude organic heteromonocyclic parent (CHEBI:35559 )
monocyclic heteroarene (CHEBI:35559 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013785)

Excreta

Biofluid or Excreta

Urine (PMID: 22284503)
Feces (PMID: 24811995)

Cellular substructure

Cytoplasm (HMDB: HMDB0013785)
Extracellular (HMDB: HMDB0013785)

Source

Endogenous

Endogenous (HMDB: HMDB0013785)

Process

Not Available

Role

Biological role

Carcinogenic agent (HMDB: HMDB0013785)
Hepatotoxic agent (HMDB: HMDB0013785)

Indirect biological role

Maillard reaction product (HMDB: HMDB0013785)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-85.6 °C	Not Available
Boiling Point	32.00 °C. @ 758.00 mm Hg	The Good Scents Company Information System
Water Solubility	10 mg/mL at 25 °C	Not Available
LogP	1.34	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	15.9 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.11	ChemAxon
logS	-0.63	ALOGPS
pKa (Strongest Basic)	-2.9	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	18.57 m³·mol⁻¹	ChemAxon
Polarizability	6.68 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]+	107.588	31661259
DarkChem	[M-H]-	101.299	31661259
DeepCCS	[M+H]+	119.947	30932474
DeepCCS	[M-H]-	117.683	30932474
DeepCCS	[M-2H]-	153.574	30932474
DeepCCS	[M+Na]+	128.101	30932474
AllCCS	[M+H]+	112.3	32859911
AllCCS	[M+H-H2O]+	106.8	32859911
AllCCS	[M+NH4]+	117.4	32859911
AllCCS	[M+Na]+	118.9	32859911
AllCCS	[M-H]-	115.0	32859911
AllCCS	[M+Na-2H]-	119.4	32859911
AllCCS	[M+HCOO]-	124.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Furan	O1C=CC=C1	799.4	Standard polar	33892256
Furan	O1C=CC=C1	488.8	Standard non polar	33892256
Furan	O1C=CC=C1	491.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Furan EI-B (Non-derivatized)	splash10-00kr-9000000000-4c50652f33a401ab3cae	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furan EI-B (Non-derivatized)	splash10-00kr-9000000000-d007e0256578ac930b22	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furan EI-B (Non-derivatized)	splash10-00kr-9000000000-4c50652f33a401ab3cae	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furan EI-B (Non-derivatized)	splash10-00kr-9000000000-d007e0256578ac930b22	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kr-9000000000-3bddc12b5a8dd3ca188d	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 - Furan 10V, Positive-QTOF	splash10-014i-9000000000-511af11e910184693aa1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 20V, Positive-QTOF	splash10-014i-9000000000-fd05695071ee559e9be4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 40V, Positive-QTOF	splash10-014i-9000000000-208e5dd03db999e390ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 10V, Negative-QTOF	splash10-014i-9000000000-351aa9d338efe69d31ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 20V, Negative-QTOF	splash10-014i-9000000000-acebecda0e70274875b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 40V, Negative-QTOF	splash10-014i-9000000000-1df91dbb0164452d0fd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 10V, Positive-QTOF	splash10-014u-9000000000-41895048238024d76bc7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 20V, Positive-QTOF	splash10-00ku-9000000000-a223589b20bc67c79fe0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 40V, Positive-QTOF	splash10-0udr-9000000000-056962459138c52c54c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 10V, Negative-QTOF	splash10-00kf-9000000000-983ab9ff6334b0b9a584	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 20V, Negative-QTOF	splash10-00ke-9000000000-77469f3e4a080d7d3681	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furan 40V, Negative-QTOF	splash10-00kg-9000000000-d4fe1a89a559171ed26a	2021-09-22	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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	24811995	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	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	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)	Both	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

Not Available

KNApSAcK ID

C00000095

Chemspider ID

7738

KEGG Compound ID

C14275

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Furan

METLIN ID

Not Available

PubChem Compound

8029

PDB ID

Not Available

ChEBI ID

35559

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1044201

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Moro S, Chipman JK, Wegener JW, Hamberger C, Dekant W, Mally A: Furan in heat-treated foods: formation, exposure, toxicity, and aspects of risk assessment. Mol Nutr Food Res. 2012 Aug;56(8):1197-211. doi: 10.1002/mnfr.201200093. Epub 2012 May 29. [PubMed:22641279 ]
Seok YJ, Her JY, Kim YG, Kim MY, Jeong SY, Kim MK, Lee JY, Kim CI, Yoon HJ, Lee KG: [Not Available]. Toxicol Res. 2015 Sep;31(3):241-53. doi: 10.5487/TR.2015.31.3.241. [PubMed:26483883 ]

Showing metabocard for Furan (HMDB0013785)

MOL for HMDB0013785 (Furan)

3D MOL for HMDB0013785 (Furan)

3D SDF for HMDB0013785 (Furan)

3D-SDF for HMDB0013785 (Furan)

PDB for HMDB0013785 (Furan)

3D PDB for HMDB0013785 (Furan)

SMILES for HMDB0013785 (Furan)

INCHI for HMDB0013785 (Furan)

Structure for HMDB0013785 (Furan)

3D Structure for HMDB0013785 (Furan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra