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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:53:11 UTC

Update Date

2023-02-21 17:22:58 UTC

HMDB ID

HMDB0033002

Secondary Accession Numbers

HMDB33002

Metabolite Identification

Common Name

5-Methyl-2-furancarboxaldehyde

Description

5-Methyl-2-furancarboxaldehyde, also known as 5-methyl-2-furfural or 2-formyl-5-methylfuran, belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. 5-Methyl-2-furancarboxaldehyde is an almond, burnt sugar, and caramel tasting compound. 5-methyl-2-furancarboxaldehyde has been detected, but not quantified, in several different foods, such as green bell peppers, red bell peppers, pepper (c. frutescens), orange bell peppers, and pepper (c. annuum). This could make 5-methyl-2-furancarboxaldehyde a potential biomarker for the consumption of these foods.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Methyl-2-furfural	Kegg
2-Formyl-5-methylfuran	HMDB
2-Methyl-5-formylfuran	HMDB
5-Methyl furfural	HMDB
5-Methyl-2-furanaldehyde	HMDB
5-Methyl-2-furancarbaldehyde	HMDB
5-Methyl-2-furancarboxyaldehyde	HMDB
5-Methyl-2-furfuraldehyde	HMDB
5-Methyl-furfural	HMDB
5-Methylfuran-2-al	HMDB
5-Methylfuran-2-carbaldehyde	HMDB
5-Methylfurfural	HMDB
5-Methylfurfuraldehyde	HMDB
alpha-Methylfurfural	HMDB
FEMA 2702	HMDB
Methyl-5-furfural	HMDB
Methylfurfural	MeSH
5-Methyl-2-furaldehyde	MeSH

Chemical Formula

C₆H₆O₂

Average Molecular Weight

110.1106

Monoisotopic Molecular Weight

110.036779436

IUPAC Name

5-methylfuran-2-carbaldehyde

Traditional Name

5-methylfurfural

CAS Registry Number

620-02-0

SMILES

CC1=CC=C(O1)C=O

InChI Identifier

InChI=1S/C6H6O2/c1-5-2-3-6(4-7)8-5/h2-4H,1H3

InChI Key

OUDFNZMQXZILJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-aldehydes

Alternative Parents

Substituents

Aryl-aldehyde
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

arenecarbaldehyde (CHEBI:2091 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0033002)
Cytoplasm (HMDB: HMDB0033002)

Excreta

Biofluid or Excreta

Feces (HMDB: HMDB0033002)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033002)

Source

Endogenous

Plant

Plant (HMDB: HMDB0033002)

Exogenous

Food

Food (HMDB: HMDB0033002)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Fruit

Tropical fruit

Tamarind (FooDB: FOOD00180)

Not Available

Nutrient (HMDB: HMDB0033002)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033002)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	89.00 to 90.00 °C. @ 26.00 mm Hg	The Good Scents Company Information System
Water Solubility	29110 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.67	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	14.9 g/L	ALOGPS
logP	0.69	ALOGPS
logP	0.95	ChemAxon
logS	-0.87	ALOGPS
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	30.18 m³·mol⁻¹	ChemAxon
Polarizability	11.1 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]+	122.106	31661259
DarkChem	[M-H]-	118.561	31661259
DeepCCS	[M+H]+	124.395	30932474
DeepCCS	[M-H]-	121.967	30932474
DeepCCS	[M-2H]-	158.431	30932474
DeepCCS	[M+Na]+	133.088	30932474
AllCCS	[M+H]+	120.6	32859911
AllCCS	[M+H-H2O]+	115.6	32859911
AllCCS	[M+NH4]+	125.3	32859911
AllCCS	[M+Na]+	126.6	32859911
AllCCS	[M-H]-	118.8	32859911
AllCCS	[M+Na-2H]-	121.2	32859911
AllCCS	[M+HCOO]-	123.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methyl-2-furancarboxaldehyde	CC1=CC=C(O1)C=O	1616.7	Standard polar	33892256
5-Methyl-2-furancarboxaldehyde	CC1=CC=C(O1)C=O	919.0	Standard non polar	33892256
5-Methyl-2-furancarboxaldehyde	CC1=CC=C(O1)C=O	959.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde CI-B (Non-derivatized)	splash10-03di-0900000000-a5a13e591b36b86e11b6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde EI-B (Non-derivatized)	splash10-0nmi-8900000000-5ccf71472dd6f90fd628	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde EI-B (Non-derivatized)	splash10-0ik9-9500000000-a4ea6639be196a5f2f38	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde EI-B (Non-derivatized)	splash10-114i-9700000000-9e971b7e848b7697026f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde CI-B (Non-derivatized)	splash10-03di-0900000000-a5a13e591b36b86e11b6	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde EI-B (Non-derivatized)	splash10-0nmi-8900000000-5ccf71472dd6f90fd628	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde EI-B (Non-derivatized)	splash10-0ik9-9500000000-a4ea6639be196a5f2f38	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde EI-B (Non-derivatized)	splash10-114i-9700000000-9e971b7e848b7697026f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-9400000000-5c85af2fdb6928c0e667	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Methyl-2-furancarboxaldehyde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0nmi-8900000000-ebe250fc2bb6f6b2db63	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 - 5-Methyl-2-furancarboxaldehyde 10V, Positive-QTOF	splash10-03di-0900000000-c63b19ba1fb01c3f73c7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 20V, Positive-QTOF	splash10-03di-5900000000-e191ecce20ba1f4b3c42	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 40V, Positive-QTOF	splash10-0udi-9000000000-c8cb53cf4ecdff620947	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 10V, Negative-QTOF	splash10-0a4i-0900000000-8e0efc57ee7fbf5bb4bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 20V, Negative-QTOF	splash10-0a4i-4900000000-776db841f073bbf3d98f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 40V, Negative-QTOF	splash10-014j-9000000000-ee3f66e726955f16f50d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 10V, Positive-QTOF	splash10-0ik9-9500000000-47f08c50e06597c77e0c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 20V, Positive-QTOF	splash10-0kv3-9000000000-f6f1137a9c602b5fbac0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 40V, Positive-QTOF	splash10-0udr-9000000000-f1fb7f3506e3e5e4c2bf	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 10V, Negative-QTOF	splash10-0pc0-9600000000-2e8a9bc3b664619f4ae3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 20V, Negative-QTOF	splash10-01q9-9000000000-00cedf36d1d313c39f4a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Methyl-2-furancarboxaldehyde 40V, Negative-QTOF	splash10-03yi-9000000000-7291694296b0cf2beb37	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

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	24811995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	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	Intestinal infections	14684577	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

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 ]
Enteritis
Probert CS, Jones PR, Ratcliffe NM: A novel method for rapidly diagnosing the causes of diarrhoea. Gut. 2004 Jan;53(1):58-61. [PubMed:14684577 ]

Associated OMIM IDs

266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12097

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1032681

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 5-Methyl-2-furancarboxaldehyde (HMDB0033002)

MOL for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

3D MOL for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

3D SDF for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

3D-SDF for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

PDB for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

3D PDB for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

SMILES for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

INCHI for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

Structure for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

3D Structure for HMDB0033002 (5-Methyl-2-furancarboxaldehyde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra