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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:16:02 UTC

Update Date

2022-03-07 02:54:27 UTC

HMDB ID

HMDB0035307

Secondary Accession Numbers

HMDB35307

Metabolite Identification

Common Name

Quercuslactone a

Description

Quercuslactone a 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. Quercuslactone a is a burnt, celery, and coconut tasting compound. Quercuslactone a has been detected, but not quantified in, alcoholic beverages. This could make quercuslactone a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Quercuslactone a.

Structure

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

COMPND    HMDB0035307
HETATM    1  C1  UNL     1       4.075  -0.203  -0.282  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.821  -0.849   0.265  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.636  -0.061  -0.224  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.325  -0.614   0.260  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.760   0.279  -0.310  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.553   1.591   0.160  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.719   2.201   0.532  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.911   3.317   1.076  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.827   1.279   0.172  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.122  -0.071   0.234  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.830  -1.126  -0.544  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.623   0.312   0.560  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.835   0.608  -1.025  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.750  -0.961  -0.691  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.755  -1.887  -0.177  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.874  -0.936   1.349  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.611  -0.080  -1.331  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.717   0.977   0.171  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.149  -1.657  -0.060  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.228  -0.576   1.365  1.00  0.00           H  
HETATM   21  H10 UNL     1      -0.721   0.271  -1.403  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.217   1.473  -0.858  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.629   1.260   0.933  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.997  -0.301   1.311  1.00  0.00           H  
HETATM   25  H14 UNL     1      -2.316  -1.436  -1.465  1.00  0.00           H  
HETATM   26  H15 UNL     1      -3.875  -0.783  -0.788  1.00  0.00           H  
HETATM   27  H16 UNL     1      -2.922  -2.026   0.107  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   10   21
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   22   23
CONECT   10   11   24
CONECT   11   25   26   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-Whiskylactone	HMDB
T-Whiskylactone	HMDB
trans-Whiskeylactone	HMDB
beta-Methyl-gamma-octalactone	MeSH, HMDB
3-Methyl-4-butyl-g-butyrolactone	Generator
3-Methyl-4-butyl-γ-butyrolactone	Generator

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

5-butyl-4-methyloxolan-2-one

Traditional Name

cis-3-methyl-4-octanolide

CAS Registry Number

80041-01-6

SMILES

CCCCC1OC(=O)CC1C

InChI Identifier

InChI=1S/C9H16O2/c1-3-4-5-8-7(2)6-9(10)11-8/h7-8H,3-6H2,1-2H3

InChI Key

WNVCMFHPRIBNCW-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
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Exogenous (HMDB: HMDB0035307)

Food

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Not Available

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	0.85 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.34	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-7	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	3	ChemAxon
Refractivity	42.92 m³·mol⁻¹	ChemAxon
Polarizability	18.11 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]+	135.512	31661259
DarkChem	[M-H]-	133.581	31661259
DeepCCS	[M+H]+	142.112	30932474
DeepCCS	[M-H]-	139.919	30932474
DeepCCS	[M-2H]-	176.242	30932474
DeepCCS	[M+Na]+	151.27	30932474
AllCCS	[M+H]+	136.0	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	140.1	32859911
AllCCS	[M+Na]+	141.2	32859911
AllCCS	[M-H]-	139.3	32859911
AllCCS	[M+Na-2H]-	140.8	32859911
AllCCS	[M+HCOO]-	142.6	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.	5.1 minutes	32390414
Predicted by Siyang on May 30, 2022	16.3098 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.45 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2267.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	556.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	208.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	356.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	696.0 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	726.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1334.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	462.7 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	1497.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	543.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	533.4 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	35.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quercuslactone a	CCCCC1OC(=O)CC1C	1932.1	Standard polar	33892256
Quercuslactone a	CCCCC1OC(=O)CC1C	1256.7	Standard non polar	33892256
Quercuslactone a	CCCCC1OC(=O)CC1C	1311.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Quercuslactone a EI-B (Non-derivatized)	splash10-0007-9000000000-52b91f8a190dc4d70837	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Quercuslactone a EI-B (Non-derivatized)	splash10-0007-9000000000-52b91f8a190dc4d70837	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quercuslactone a GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-7bc62b21db7f07d62ea5	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quercuslactone a GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quercuslactone a 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 - Quercuslactone a 10V, Positive-QTOF	splash10-0a4i-2900000000-eb60924d7db73dd90686	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 20V, Positive-QTOF	splash10-066s-9400000000-a3cfdd4ac40cb7f70218	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 40V, Positive-QTOF	splash10-052f-9000000000-bf75c35ed005be1d8a74	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 10V, Negative-QTOF	splash10-0a4i-1900000000-764fd7c479fc1a34fab7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 20V, Negative-QTOF	splash10-0bt9-2900000000-0d927d1c064257fc8d86	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 40V, Negative-QTOF	splash10-052f-9200000000-42902cc652512e92509c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 10V, Positive-QTOF	splash10-0aor-5900000000-ec46ff9f1bd0520d6263	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 20V, Positive-QTOF	splash10-00kf-9300000000-a3d29faf9e9c8b8eeddd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 40V, Positive-QTOF	splash10-0006-9000000000-ef700877a2790c9bfd8d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 10V, Negative-QTOF	splash10-0a4i-0900000000-376389ca50b091133eac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 20V, Negative-QTOF	splash10-0a4i-8900000000-1b158ebc705577d08545	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quercuslactone a 40V, Negative-QTOF	splash10-0006-9200000000-d89cdf27c92c75ba6b1d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB014730

KNApSAcK ID

Not Available

Chemspider ID

56625

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62900

PDB ID

Not Available

ChEBI ID

Not Available

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 Quercuslactone a (HMDB0035307)

MOL for HMDB0035307 (Quercuslactone a)

3D MOL for HMDB0035307 (Quercuslactone a)

3D SDF for HMDB0035307 (Quercuslactone a)

3D-SDF for HMDB0035307 (Quercuslactone a)

PDB for HMDB0035307 (Quercuslactone a)

3D PDB for HMDB0035307 (Quercuslactone a)

SMILES for HMDB0035307 (Quercuslactone a)

INCHI for HMDB0035307 (Quercuslactone a)

Structure for HMDB0035307 (Quercuslactone a)

3D Structure for HMDB0035307 (Quercuslactone a)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra