MiMeDB: Showing metabocard for 3-Hydroxy-2-methyl-4-pyrone (MMDBc0033571)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:54:04 UTC

Update Date

2024-09-27 23:38:38 UTC

Metabolite ID

MMDBc0033571

Metabolite Identification

Common Name

3-Hydroxy-2-methyl-4-pyrone

Description

Maltol (3-Hydroxy-2-methyl-4-pyrone) is a naturally occurring organic compound found in the bark of larch tree, pine needles and in roasted malt. Because it has the odor of cotton candy and caramel, maltol is used as a flavor enhancer (E636) in breads and cakes to impart a sweet aroma to fragrances.

Structure

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

Synonyms

Value	Source
e636	ChEMBL, HMDB
2-Hydroxy-3-methyl-4H-pyran-4-one	HMDB
2-Methyl pyromeconic acid	HMDB
2-Methyl-3-hydroxy-4-pyranone	HMDB
2-Methyl-3-hydroxy-4-pyrone	HMDB
2-Methyl-3-hydroxypyrone	HMDB
2-Methyl-3-oxy-gamma-pyrone	HMDB
3-Hydroxy-2-methyl-1,4-pyrone	HMDB
3-Hydroxy-2-methyl-4-pyranone	HMDB
3-Hydroxy-2-methyl-4-pyrone	HMDB, MeSH
3-Hydroxy-2-methyl-4H-pyran-4-one	HMDB
3-Hydroxy-2-methyl-g-pyrone	HMDB
3-Hydroxy-2-methyl-gamma-pyrone	HMDB
3-Hydroxy-2-methylpyrone	HMDB
3-Hydroxy-2-pyran-4-one	HMDB
5-Hydroxy-6-methyl-4H-pyran-4-one	HMDB
FEMA 2656	HMDB
Laricinic acid	HMDB
Larixic acid	HMDB
Larixinic acid	HMDB
Palatone	HMDB
Talmon	HMDB
Veltol	HMDB
Vetol	HMDB

Molecular Formula

C₆H₆O₃

Average Mass

126.11

Monoisotopic Mass

126.031694058

IUPAC Name

3-hydroxy-2-methyl-4H-pyran-4-one

Traditional Name

talmon

CAS Registry Number

118-71-8

SMILES

CC1=C(O)C(=O)C=CO1

InChI Identifier

InChI=1S/C6H6O3/c1-4-6(8)5(7)2-3-9-4/h2-3,8H,1H3

InChI Key

XPCTZQVDEJYUGT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Cyclic ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyranone (CHEBI:69438 )
Monocyclic gamma-pyrones (C11918 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	134 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	0.55	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.72 m³·mol⁻¹	ChemAxon
Polarizability	11.6 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9500000000-9ab04dd29d36893ecd26	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05ir-7900000000-600ebd59fb3066652709	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-9000000000-c04cc7216a3bd4a235e7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-4900000000-aa92125c58514d72564e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-683526173a1cb2e60e9a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-4900000000-9cacfb0610f4c652bbfd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-68373306ed89c51d3c8e	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-38440dc8d01235ec6030	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-d055c9796b264b599b6a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-d0af17e3cc2dd76131f3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-69feb02bb47c24872d73	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016s-9300000000-76b24f4971833037af7b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002g-9000000000-c6a03d90d227ae6c5653	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004l-6900000000-962e671fbe15160f2004	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9100000000-46cfacfee845f86dc959	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6cab6127640d08dfd89f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-3900000000-5b997e243689ece01872	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0arv-9100000000-db550e8ed4a495f56e5c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-2ce65d95643025ecae24	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-9400000000-e2ddaa7bab18abea7217	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2015-03-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)		2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)		2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food	Coffee	Coffea arabica	FooDB	31437929
Food	Coffee	Coffea canephora	FooDB	31437929
Food			FooDB	31437929
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant		Theobroma cacao	FooDB	31437929
Plant	Fruit	Rubus idaeus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

HMDB ID

HMDB0030776

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Maltol

METLIN ID

Not Available

PubChem Compound

8369

PDB ID

Not Available

ChEBI ID

142577

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 3-Hydroxy-2-methyl-4-pyrone (MMDBc0033571)

MOL for #<Metabolite:0x00007f46c5381040>

3D MOL for #<Metabolite:0x00007f46c5381040>

3D SDF for #<Metabolite:0x00007f46c5381040>

3D-SDF for #<Metabolite:0x00007f46c5381040>

PDB for #<Metabolite:0x00007f46c5381040>

3D PDB for #<Metabolite:0x00007f46c5381040>

SMILES for #<Metabolite:0x00007f46c5381040>

INCHI for #<Metabolite:0x00007f46c5381040>

Structure for #<Metabolite:0x00007f46c5381040>

3D Structure for #<Metabolite:0x00007f46c5381040>