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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:11 UTC

Update Date

2023-02-21 17:22:58 UTC

HMDB ID

HMDB0033003

Secondary Accession Numbers

HMDB33003

Metabolite Identification

Common Name

1-(5-Methyl-2-furanyl)-1,2-propanedione

Description

1-(5-Methyl-2-furanyl)-1,2-propanedione 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. 1-(5-Methyl-2-furanyl)-1,2-propanedione 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 1-(5-methyl-2-furanyl)-1,2-propanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1-(5-Methyl-2-furanyl)-1,2-propanedione.

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-furyi)-1,2-propanedione	HMDB
1-(5-Methyl-2-furyl)propane-1,2-dione	HMDB

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

1-(5-methylfuran-2-yl)propane-1,2-dione

Traditional Name

1-(5-methylfuran-2-yl)propane-1,2-dione

CAS Registry Number

1197-20-2

SMILES

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

InChI Identifier

InChI=1S/C8H8O3/c1-5-3-4-7(11-5)8(10)6(2)9/h3-4H,1-2H3

InChI Key

CSILYJHAPLAXTQ-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: HMDB0033003)
Cytoplasm (HMDB: HMDB0033003)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033003)

Source

Exogenous

Food

Food (HMDB: HMDB0033003)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0033003)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033003)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	231.00 to 232.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	16030 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.818 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.97 g/L	ALOGPS
logP	1.05	ALOGPS
logP	1.08	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	16.53	ChemAxon
pKa (Strongest Basic)	-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	39.35 m³·mol⁻¹	ChemAxon
Polarizability	15.31 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]+	132.784	31661259
DarkChem	[M-H]-	132.023	31661259
DeepCCS	[M+H]+	137.09	30932474
DeepCCS	[M-H]-	134.56	30932474
DeepCCS	[M-2H]-	170.154	30932474
DeepCCS	[M+Na]+	145.317	30932474
AllCCS	[M+H]+	130.6	32859911
AllCCS	[M+H-H2O]+	126.0	32859911
AllCCS	[M+NH4]+	134.8	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	129.4	32859911
AllCCS	[M+Na-2H]-	130.7	32859911
AllCCS	[M+HCOO]-	132.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-(5-Methyl-2-furanyl)-1,2-propanedione	CC(=O)C(=O)C1=CC=C(C)O1	1823.6	Standard polar	33892256
1-(5-Methyl-2-furanyl)-1,2-propanedione	CC(=O)C(=O)C1=CC=C(C)O1	1128.3	Standard non polar	33892256
1-(5-Methyl-2-furanyl)-1,2-propanedione	CC(=O)C(=O)C1=CC=C(C)O1	1203.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-(5-Methyl-2-furanyl)-1,2-propanedione,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(=O)C1=CC=C(C)O1	1421.1	Semi standard non polar	33892256
1-(5-Methyl-2-furanyl)-1,2-propanedione,1TMS,isomer #1	C=C(O[Si](C)(C)C)C(=O)C1=CC=C(C)O1	1333.2	Standard non polar	33892256
1-(5-Methyl-2-furanyl)-1,2-propanedione,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=C(C)O1	1639.2	Semi standard non polar	33892256
1-(5-Methyl-2-furanyl)-1,2-propanedione,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1=CC=C(C)O1	1528.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-ed8ff2d7878344b6a73c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 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 - 1-(5-Methyl-2-furanyl)-1,2-propanedione 10V, Positive-QTOF	splash10-0udr-0900000000-e3358a94cc07445c89f7	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 20V, Positive-QTOF	splash10-001i-9600000000-d6111ddbca5cbd1fe8eb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 40V, Positive-QTOF	splash10-001i-9000000000-f7a969c9d86a0166705d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 10V, Negative-QTOF	splash10-0udi-1900000000-bdb36c375ba5b0b8b64d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 20V, Negative-QTOF	splash10-0a4i-3900000000-856ac8136e4815785153	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 40V, Negative-QTOF	splash10-0l6r-9200000000-59fe5985ed2a6faf0da4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 10V, Positive-QTOF	splash10-01qc-9100000000-06ac5f2d8e2693f3a2b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 20V, Positive-QTOF	splash10-0006-9000000000-32f4f4b4790b0641ff6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 40V, Positive-QTOF	splash10-0006-9000000000-bab02ac4f5d91ece2d34	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 10V, Negative-QTOF	splash10-0pb9-2900000000-2236ad30f218a44aeac8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 20V, Negative-QTOF	splash10-0ue9-9300000000-caf28e0e78e4f86f5a1c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-(5-Methyl-2-furanyl)-1,2-propanedione 40V, Negative-QTOF	splash10-03e9-9000000000-3479a9aacda427890f72	2021-09-22	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

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

FDB010992

KNApSAcK ID

Not Available

Chemspider ID

64129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70968

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1490261

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 1-(5-Methyl-2-furanyl)-1,2-propanedione (HMDB0033003)

MOL for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

3D MOL for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

3D SDF for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

3D-SDF for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

PDB for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

3D PDB for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

SMILES for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

INCHI for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

Structure for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

3D Structure for HMDB0033003 (1-(5-Methyl-2-furanyl)-1,2-propanedione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra