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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 20:10:44 UTC

Update Date

2023-02-21 17:24:42 UTC

HMDB ID

HMDB0035226

Secondary Accession Numbers

HMDB35226

Metabolite Identification

Common Name

2-Acetyl-5-methylfuran

Description

2-Acetyl-5-methylfuran, also known as 2-methyl-5-acetylfuran, belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 2-Acetyl-5-methylfuran is a strong, coconut, and coumarin tasting compound. 2-Acetyl-5-methylfuran has been detected, but not quantified in, several different foods, such as coffee and coffee products, welsh onions (Allium fistulosum), cereals and cereal products, green tea, and robusta coffees (Coffea canephora). This could make 2-acetyl-5-methylfuran a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 2-Acetyl-5-methylfuran.

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-(5-Methyl-2-furanyl)ethanone	ChEBI
1-(5-Methyl-2-furyl)ethan-1-one	ChEBI
1-(5-Methyl-2-furyl)ethanone	ChEBI
2-Methyl-5-acetylfuran	ChEBI
5-Acetyl-2-methylfuran	ChEBI
5-Methyl-2-acetylfuran	ChEBI
5-Methyl-2-furylmethylketone	ChEBI
Methyl 5-methyl-2-furyl ketone	ChEBI
1-(5-Methyl-2-furanyl)-ethanone	HMDB
1-(5-Methyl-2-furanyl)ethanone, 9ci	HMDB
1-(5-Methylfuran-2-yl)ethanone	HMDB
2-Acetyl, 5-mefuran	HMDB
2-Acetyl-5-methyl-furan	HMDB
FEMA 3069	HMDB
Ketone, methyl 5-methyl-2-furyl	HMDB
Methyl (5-methyl-2-furyl) ketone, 8ci	HMDB

Chemical Formula

C₇H₈O₂

Average Molecular Weight

124.1372

Monoisotopic Molecular Weight

124.0524295

IUPAC Name

1-(5-methylfuran-2-yl)ethan-1-one

Traditional Name

2-acetyl-5-methylfuran

CAS Registry Number

1193-79-9

SMILES

CC(=O)C1=CC=C(C)O1

InChI Identifier

InChI=1S/C7H8O2/c1-5-3-4-7(9-5)6(2)8/h3-4H,1-2H3

InChI Key

KEFJLCGVTHRGAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

methyl ketone (CHEBI:562752 )
furans (CHEBI:562752 )
aromatic ketone (CHEBI:562752 )

Ontology

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Cellular substructure

Extracellular (HMDB: HMDB0035226)
Cytoplasm (HMDB: HMDB0035226)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035226)

Source

Exogenous

Exogenous (HMDB: HMDB0035226)

Food

Food (HMDB: HMDB0035226)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Tea

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Aquatic origin

Fish

Fishes (FooDB: FOOD00865)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0035226)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0035226)

Biological role

Nutrient (HMDB: HMDB0035226)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	100.00 to 101.00 °C. @ 25.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	0.356 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.7 g/L	ALOGPS
logP	0.94	ALOGPS
logP	0.79	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34 m³·mol⁻¹	ChemAxon
Polarizability	13.15 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]+	125.296	31661259
DarkChem	[M-H]-	123.99	31661259
DeepCCS	[M+H]+	131.722	30932474
DeepCCS	[M-H]-	129.259	30932474
DeepCCS	[M-2H]-	165.124	30932474
DeepCCS	[M+Na]+	140.057	30932474
AllCCS	[M+H]+	123.4	32859911
AllCCS	[M+H-H2O]+	118.6	32859911
AllCCS	[M+NH4]+	128.0	32859911
AllCCS	[M+Na]+	129.3	32859911
AllCCS	[M-H]-	123.1	32859911
AllCCS	[M+Na-2H]-	125.1	32859911
AllCCS	[M+HCOO]-	127.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.57 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5692 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1354.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	470.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	301.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	115.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	578.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	242.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	982.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	365.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1078.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	359.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	491.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	404.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	62.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Acetyl-5-methylfuran	CC(=O)C1=CC=C(C)O1	1613.2	Standard polar	33892256
2-Acetyl-5-methylfuran	CC(=O)C1=CC=C(C)O1	998.9	Standard non polar	33892256
2-Acetyl-5-methylfuran	CC(=O)C1=CC=C(C)O1	1018.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetyl-5-methylfuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-0khc-9300000000-5ac9d4d2fdc967ceca15	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Acetyl-5-methylfuran GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-6900000000-95c4649eabdbb5ade9b9	2015-03-01	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-Acetyl-5-methylfuran 10V, Positive-QTOF	splash10-056r-0900000000-6ce869c65e1058a03117	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 20V, Positive-QTOF	splash10-0a6r-2900000000-7fb693037561886dbdda	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 40V, Positive-QTOF	splash10-0zfr-9200000000-a42b59e5a84da1172106	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 10V, Negative-QTOF	splash10-00di-0900000000-160cb761466061d3dbf6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 20V, Negative-QTOF	splash10-00e9-9700000000-cc7ec9b57881d6d58f63	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 40V, Negative-QTOF	splash10-0pdm-9200000000-a3d276f36fe7972f3cff	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 10V, Negative-QTOF	splash10-0089-9600000000-8796550e8d91fd10c997	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 20V, Negative-QTOF	splash10-0w9c-9100000000-93dc23d3bf73a0207b18	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 40V, Negative-QTOF	splash10-000m-9000000000-30df1072d8b06a3c56f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 10V, Positive-QTOF	splash10-000x-9100000000-8f790fe0569672ba5a2f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 20V, Positive-QTOF	splash10-0006-9000000000-a2de2905fc3573f3d52c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Acetyl-5-methylfuran 40V, Positive-QTOF	splash10-0f76-9000000000-d0be99d6117a45383b46	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

Feces
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21280206	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21280206	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21280206	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	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	17314143	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013878

KNApSAcK ID

Not Available

Chemspider ID

13858

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Acetyl-5-methylfuran

METLIN ID

Not Available

PubChem Compound

14514

PDB ID

Not Available

ChEBI ID

562752

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027731

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-Acetyl-5-methylfuran (HMDB0035226)

MOL for HMDB0035226 (2-Acetyl-5-methylfuran)

3D MOL for HMDB0035226 (2-Acetyl-5-methylfuran)

3D SDF for HMDB0035226 (2-Acetyl-5-methylfuran)

3D-SDF for HMDB0035226 (2-Acetyl-5-methylfuran)

PDB for HMDB0035226 (2-Acetyl-5-methylfuran)

3D PDB for HMDB0035226 (2-Acetyl-5-methylfuran)

SMILES for HMDB0035226 (2-Acetyl-5-methylfuran)

INCHI for HMDB0035226 (2-Acetyl-5-methylfuran)

Structure for HMDB0035226 (2-Acetyl-5-methylfuran)

3D Structure for HMDB0035226 (2-Acetyl-5-methylfuran)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra