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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:40 UTC

Update Date

2023-02-21 17:22:46 UTC

HMDB ID

HMDB0032920

Secondary Accession Numbers

HMDB32920

Metabolite Identification

Common Name

alpha-Furyl methyl diketone

Description

alpha-Furyl methyl diketone belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group. alpha-Furyl methyl diketone has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make alpha-furyl methyl diketone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on alpha-Furyl methyl diketone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
a-Furyl methyl diketone	Generator
Α-furyl methyl diketone	Generator
1-(2-Furanyl)-1,2-propanedione	HMDB
1-(2-Furyl)-1,2-propanedione	HMDB
1-(2-Furyl)propane-1,2-dione	HMDB

Chemical Formula

C₇H₆O₃

Average Molecular Weight

138.1207

Monoisotopic Molecular Weight

138.031694058

IUPAC Name

1-(furan-2-yl)propane-1,2-dione

Traditional Name

1-(furan-2-yl)propane-1,2-dione

CAS Registry Number

1438-92-2

SMILES

CC(=O)C(=O)C1=CC=CO1

InChI Identifier

InChI=1S/C7H6O3/c1-5(8)7(9)6-3-2-4-10-6/h2-4H,1H3

InChI Key

JXZJRYDTSDCGLO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl ketones. These are organic aromatic compounds that contain a ketone group substituted at one C-atom with an aryl group. They have the generic structure RC(=O)R', where R = aryl group and R'=organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl ketones

Alternative Parents

Substituents

Aryl ketone
Alpha-diketone
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032920)
Cytoplasm (HMDB: HMDB0032920)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032920)

Source

Exogenous

Exogenous (HMDB: HMDB0032920)

Food

Food (HMDB: HMDB0032920)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0032920)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032920)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60 - 61 °C	Not Available
Boiling Point	198.00 to 199.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	53990 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.751 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.9 g/L	ALOGPS
logP	0.66	ALOGPS
logP	0.88	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	16.51	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	47.28 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	34.2 m³·mol⁻¹	ChemAxon
Polarizability	13.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.432	31661259
DarkChem	[M-H]-	125.328	31661259
DeepCCS	[M+H]+	134.585	30932474
DeepCCS	[M-H]-	132.295	30932474
DeepCCS	[M-2H]-	168.149	30932474
DeepCCS	[M+Na]+	142.69	30932474
AllCCS	[M+H]+	127.5	32859911
AllCCS	[M+H-H2O]+	122.8	32859911
AllCCS	[M+NH4]+	131.9	32859911
AllCCS	[M+Na]+	133.2	32859911
AllCCS	[M-H]-	124.1	32859911
AllCCS	[M+Na-2H]-	125.7	32859911
AllCCS	[M+HCOO]-	127.5	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.	3.51 minutes	32390414
Predicted by Siyang on May 30, 2022	11.5032 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.37 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1317.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	436.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	277.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	109.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	358.6 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	522.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	208.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	913.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	323.3 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	1045.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	313.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	478.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	365.3 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	84.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Furyl methyl diketone	CC(=O)C(=O)C1=CC=CO1	1738.7	Standard polar	33892256
alpha-Furyl methyl diketone	CC(=O)C(=O)C1=CC=CO1	1010.0	Standard non polar	33892256
alpha-Furyl methyl diketone	CC(=O)C(=O)C1=CC=CO1	1078.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Furyl methyl diketone,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(=O)C1=CC=CO1	1272.7	Semi standard non polar	33892256
alpha-Furyl methyl diketone,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(=O)C1=CC=CO1	1215.3	Standard non polar	33892256
alpha-Furyl methyl diketone,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CO1	1492.9	Semi standard non polar	33892256
alpha-Furyl methyl diketone,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=CO1	1398.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Furyl methyl diketone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-99462dd9f204f1ba41f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Furyl methyl diketone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 10V, Positive-QTOF	splash10-0079-0900000000-33d3930ce9664ebc6586	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 20V, Positive-QTOF	splash10-00dr-2900000000-a16498161daa3a35ff29	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 40V, Positive-QTOF	splash10-00di-3900000000-9280b83b3c6528011793	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 10V, Negative-QTOF	splash10-000i-2900000000-083508b423373d5d9308	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 20V, Negative-QTOF	splash10-000b-9700000000-3de2a16ab902a6f40df7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 40V, Negative-QTOF	splash10-014i-9200000000-796a107a789a3bf05e1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 10V, Negative-QTOF	splash10-014r-9400000000-68b5b4e99a3f4450facb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 20V, Negative-QTOF	splash10-014i-9000000000-f2d63a9ab2048bb8e006	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 40V, Negative-QTOF	splash10-014i-9000000000-b213421ed5e5deb05e9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 10V, Positive-QTOF	splash10-000g-9200000000-b3bbbb292820531977e5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 20V, Positive-QTOF	splash10-0006-9000000000-bd9f67bf1a01571a72a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Furyl methyl diketone 40V, Positive-QTOF	splash10-0006-9000000000-842b81af5a1935d98a20	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]+)	2023-02-04	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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010903

KNApSAcK ID

Not Available

Chemspider ID

66657

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74038

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1485381

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 alpha-Furyl methyl diketone (HMDB0032920)

MOL for HMDB0032920 (alpha-Furyl methyl diketone)

3D MOL for HMDB0032920 (alpha-Furyl methyl diketone)

3D SDF for HMDB0032920 (alpha-Furyl methyl diketone)

3D-SDF for HMDB0032920 (alpha-Furyl methyl diketone)

PDB for HMDB0032920 (alpha-Furyl methyl diketone)

3D PDB for HMDB0032920 (alpha-Furyl methyl diketone)

SMILES for HMDB0032920 (alpha-Furyl methyl diketone)

INCHI for HMDB0032920 (alpha-Furyl methyl diketone)

Structure for HMDB0032920 (alpha-Furyl methyl diketone)

3D Structure for HMDB0032920 (alpha-Furyl methyl diketone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra