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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:59:57 UTC

Update Date

2022-03-07 02:53:39 UTC

HMDB ID

HMDB0033286

Secondary Accession Numbers

HMDB33286

Metabolite Identification

Common Name

Sherry lactone

Description

Sherry lactone 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. Sherry lactone has been detected, but not quantified in, alcoholic beverages and root vegetables. This could make sherry lactone a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Sherry lactone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3,6-Trideoxy-1,4-hexonolactone	HMDB
5-Hydroxy-4-hexanolide	HMDB
dihydro-5-(1-Hydroxyethyl)-2(3H)-furanone	HMDB

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

5-(1-hydroxyethyl)oxolan-2-one

Traditional Name

5-(1-hydroxyethyl)oxolan-2-one

CAS Registry Number

54656-51-8

SMILES

CC(O)C1CCC(=O)O1

InChI Identifier

InChI=1S/C6H10O3/c1-4(7)5-2-3-6(8)9-5/h4-5,7H,2-3H2,1H3

InChI Key

KBLZKAKKJPDYKJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033286)
Cytoplasm (HMDB: HMDB0033286)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033286)

Source

Exogenous

Food

Food (HMDB: HMDB0033286)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0033286)

Not Available

Nutrient (HMDB: HMDB0033286)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	382 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.064	ChemAxon
logS	0.47	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	30.69 m³·mol⁻¹	ChemAxon
Polarizability	12.93 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]+	126.928	31661259
DarkChem	[M-H]-	120.564	31661259
DeepCCS	[M+H]+	127.567	30932474
DeepCCS	[M-H]-	125.312	30932474
DeepCCS	[M-2H]-	161.563	30932474
DeepCCS	[M+Na]+	136.19	30932474
AllCCS	[M+H]+	129.3	32859911
AllCCS	[M+H-H2O]+	124.6	32859911
AllCCS	[M+NH4]+	133.6	32859911
AllCCS	[M+Na]+	134.9	32859911
AllCCS	[M-H]-	126.1	32859911
AllCCS	[M+Na-2H]-	128.2	32859911
AllCCS	[M+HCOO]-	130.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sherry lactone	CC(O)C1CCC(=O)O1	2340.6	Standard polar	33892256
Sherry lactone	CC(O)C1CCC(=O)O1	1159.0	Standard non polar	33892256
Sherry lactone	CC(O)C1CCC(=O)O1	1260.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sherry lactone,1TMS,isomer #1	CC(O[Si](C)(C)C)C1CCC(=O)O1	1329.1	Semi standard non polar	33892256
Sherry lactone,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C1CCC(=O)O1	1570.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sherry lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-9000000000-80fdf75de9711539d40d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sherry lactone GC-MS (1 TMS) - 70eV, Positive	splash10-009l-9300000000-2141d18146d8ed99eece	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sherry lactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sherry lactone 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 - Sherry lactone 10V, Positive-QTOF	splash10-001i-2900000000-82ccbce7a0b7c00f8e61	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 20V, Positive-QTOF	splash10-0gx0-9800000000-dcd559f2333f19d1fc91	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 40V, Positive-QTOF	splash10-0udi-9000000000-97808d884ace3a784e8f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 10V, Negative-QTOF	splash10-004i-2900000000-f57adc30280411c81814	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 20V, Negative-QTOF	splash10-01ti-9800000000-9e2e86e138b0ae6a49b9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 40V, Negative-QTOF	splash10-0006-9000000000-436f64c083639998c3ce	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 10V, Negative-QTOF	splash10-004i-3900000000-9986a3086f84ef184d38	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 20V, Negative-QTOF	splash10-0006-9000000000-a2dcd4ba4da654b11ac0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 40V, Negative-QTOF	splash10-052f-9000000000-6fddd0677cc3d57835a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 10V, Positive-QTOF	splash10-0002-9400000000-6943e6afb867878b5b57	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 20V, Positive-QTOF	splash10-0002-9100000000-68a6c93a4593064d6225	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sherry lactone 40V, Positive-QTOF	splash10-00ke-9000000000-539a2fec133ad94efdc8	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

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

FDB011309

KNApSAcK ID

C00057432

Chemspider ID

91163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100900

PDB ID

Not Available

ChEBI ID

173518

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Sherry lactone (HMDB0033286)

MOL for HMDB0033286 (Sherry lactone)

3D MOL for HMDB0033286 (Sherry lactone)

3D SDF for HMDB0033286 (Sherry lactone)

3D-SDF for HMDB0033286 (Sherry lactone)

PDB for HMDB0033286 (Sherry lactone)

3D PDB for HMDB0033286 (Sherry lactone)

SMILES for HMDB0033286 (Sherry lactone)

INCHI for HMDB0033286 (Sherry lactone)

Structure for HMDB0033286 (Sherry lactone)

3D Structure for HMDB0033286 (Sherry lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra