MiMeDB: Showing metabocard for 4-Hexanolide (MMDBc0033582)

Plant

Xenobiotic

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:54:30 UTC

Update Date

2024-09-29 03:52:55 UTC

Metabolite ID

MMDBc0033582

Metabolite Identification

Common Name

4-Hexanolide

Description

Gamma-Caprolactone, also known as 4-ethyl-4-butanolide or 4-hexanolide, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, Gamma-caprolactone is considered to be a fatty ester lipid molecule. Gamma-Caprolactone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Gamma-Caprolactone exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, Gamma-caprolactone has been detected, but not quantified in several different foods, such as potato, cereals and cereal products, pomes, alcoholic beverages, and fruits. It is occasionally found as a volatile component of human urine. In some cases differences up to an order of magnitude are observed. It has been also found in the polar fraction of human blood.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Ethyl-4-butanolide	ChEBI
4-Hexanolide	ChEBI
4-Hydroxyhexanoic acid lactone	ChEBI
5-Ethyltetrahydro-2-furanone	ChEBI
6-Caprolactone	ChEBI
Dihydro-5-ethyl-2(3H)-furanone	ChEBI
gamma-Ethyl-N-butyrolactone	ChEBI
gamma-Ethylbutyrolactone	ChEBI
gamma-Hexanolactone	ChEBI
4-Hydroxyhexanoate lactone	Generator
g-Ethyl-N-butyrolactone	Generator
Γ-ethyl-N-butyrolactone	Generator
g-Ethylbutyrolactone	Generator
Γ-ethylbutyrolactone	Generator
g-Hexanolactone	Generator
Γ-hexanolactone	Generator
g-Caprolactone	Generator
Γ-caprolactone	Generator

Molecular Formula

C₆H₁₀O₂

Average Mass

114.1424

Monoisotopic Mass

114.068079564

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C6H10O2/c1-2-5-3-4-6(7)8-5/h5H,2-4H2,1H3

InChI Key

JBFHTYHTHYHCDJ-UHFFFAOYSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Liquid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	289.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-24	31.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	390.9
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	562.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	485.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	454.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1740.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	101.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	573.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	435.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	444.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	308.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	169.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	91.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	511.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	250.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	339.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1160.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1037.9

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Food Additive	U.S. Food and Drug Administration	FDA

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	17314143

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

85235

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
Thoma H, Reiner J, Spiteller G: Profiles of strongly polar and less polar acids obtained from human blood, plasma and serum by two-step ultrafiltration. J Chromatogr. 1984 Jul 13;309(1):17-32. doi: 10.1016/0378-4347(84)80002-x. [PubMed:6480763 ]
Khersonsky O, Tawfik DS: Structure-reactivity studies of serum paraoxonase PON1 suggest that its native activity is lactonase. Biochemistry. 2005 Apr 26;44(16):6371-82. doi: 10.1021/bi047440d. [PubMed:15835926 ]

Showing metabocard for 4-Hexanolide (MMDBc0033582)

MOL for #<Metabolite:0x00007f9a910ec0d0>

3D MOL for #<Metabolite:0x00007f9a910ec0d0>

3D SDF for #<Metabolite:0x00007f9a910ec0d0>

3D-SDF for #<Metabolite:0x00007f9a910ec0d0>

PDB for #<Metabolite:0x00007f9a910ec0d0>

3D PDB for #<Metabolite:0x00007f9a910ec0d0>

SMILES for #<Metabolite:0x00007f9a910ec0d0>

INCHI for #<Metabolite:0x00007f9a910ec0d0>

Structure for #<Metabolite:0x00007f9a910ec0d0>

3D Structure for #<Metabolite:0x00007f9a910ec0d0>