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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:05 UTC

Update Date

2022-03-07 02:52:15 UTC

HMDB ID

HMDB0029691

Secondary Accession Numbers

HMDB29691

Metabolite Identification

Common Name

Wine lactone

Description

Wine lactone belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Wine lactone is a sweet, coconut, and dill tasting compound. Wine lactone has been detected, but not quantified in, alcoholic beverages. This could make wine lactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Wine lactone.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.541   1.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.541  -0.226   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.207  -0.997   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.123  -0.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.123   1.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.207   2.083   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.207  -2.535   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.452  -2.535   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.452  -0.997   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.207   3.625   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.541  -3.625   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.296  -3.625   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   10                                                  
CONECT    7    3    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    4    8                                                       
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄O₂

Average Molecular Weight

166.217

Monoisotopic Molecular Weight

166.099379692

IUPAC Name

3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-one

Traditional Name

wine lactone

CAS Registry Number

182699-77-0

SMILES

CC1C2CCC(C)=CC2OC1=O

InChI Identifier

InChI=1S/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h5,7-9H,3-4H2,1-2H3

InChI Key

NQWBFQXRASPNLB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Source

Exogenous

Food

Food (HMDB: HMDB0029691)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0029691)

Endogenous

Endogenous (HMDB: HMDB0029691)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0029691)

Role

Biological role

Energy source (HMDB: HMDB0029691)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0029691)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	48 - 50 °C	Not Available
Boiling Point	285.00 to 286.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1834 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.634 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.12 g/L	ALOGPS
logP	2.37	ALOGPS
logP	2.01	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.34 m³·mol⁻¹	ChemAxon
Polarizability	18.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	137.297	31661259
DarkChem	[M-H]-	133.791	31661259
DeepCCS	[M+H]+	132.086	30932474
DeepCCS	[M-H]-	128.256	30932474
DeepCCS	[M-2H]-	165.456	30932474
DeepCCS	[M+Na]+	140.931	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	131.5	32859911
AllCCS	[M+NH4]+	140.2	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	139.6	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	141.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.64 minutes	32390414
Predicted by Siyang on May 30, 2022	13.1987 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.49 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2054.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	399.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	239.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	453.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	605.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	88.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1083.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	412.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1115.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	348.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	409.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	406.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	60.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Wine lactone	CC1C2CCC(C)=CC2OC1=O	2229.8	Standard polar	33892256
Wine lactone	CC1C2CCC(C)=CC2OC1=O	1408.5	Standard non polar	33892256
Wine lactone	CC1C2CCC(C)=CC2OC1=O	1399.3	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 - Wine lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-004l-9400000000-521a408a23ce51e6ed1d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wine 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 - Wine lactone 10V, Positive-QTOF	splash10-014i-1900000000-c114b3da9176078a9b5e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 20V, Positive-QTOF	splash10-014i-6900000000-1ad72cd7b477799c9f91	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 40V, Positive-QTOF	splash10-0fr6-9000000000-8c88f43e485a4ab8e752	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 10V, Negative-QTOF	splash10-014i-0900000000-b617020b1f5f2067d3eb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 20V, Negative-QTOF	splash10-01b9-1900000000-3e51812fd3c6233c5fb3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 40V, Negative-QTOF	splash10-06dl-9700000000-fcbc57e848ff9d1efb62	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 10V, Positive-QTOF	splash10-014i-0900000000-cba921c56abaf6d30670	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 20V, Positive-QTOF	splash10-01b9-5900000000-85deb7ab6267d384eb17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 40V, Positive-QTOF	splash10-0006-9100000000-966b9321c169dbff6e47	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 10V, Negative-QTOF	splash10-014i-0900000000-349584a3f625d5b5807f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 20V, Negative-QTOF	splash10-014i-1900000000-756ba3d9c6bf83902fc5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wine lactone 40V, Negative-QTOF	splash10-00mp-4900000000-0fcf40aeee6ed264079c	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB000878

KNApSAcK ID

Not Available

Chemspider ID

4932494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Wine lactone

METLIN ID

Not Available

PubChem Compound

6427076

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1552601

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for Wine lactone (HMDB0029691)

MOL for HMDB0029691 (Wine lactone)

3D MOL for HMDB0029691 (Wine lactone)

3D SDF for HMDB0029691 (Wine lactone)

3D-SDF for HMDB0029691 (Wine lactone)

PDB for HMDB0029691 (Wine lactone)

3D PDB for HMDB0029691 (Wine lactone)

SMILES for HMDB0029691 (Wine lactone)

INCHI for HMDB0029691 (Wine lactone)

Structure for HMDB0029691 (Wine lactone)

3D Structure for HMDB0029691 (Wine lactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra