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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:01:02 UTC

Update Date

2022-03-07 02:53:39 UTC

HMDB ID

HMDB0033302

Secondary Accession Numbers

HMDB33302

Metabolite Identification

Common Name

(4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one

Description

(4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one has been detected, but not quantified in, root vegetables. This could make (4S,6S)-3,4,5,6-tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

4-hydroxy-6-methyloxan-2-one

Traditional Name

4-hydroxy-6-methyloxan-2-one

CAS Registry Number

33275-54-6

SMILES

CC1CC(O)CC(=O)O1

InChI Identifier

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

InChI Key

KKZQBMBBMJKIRQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta_valerolactone
Delta valerolactone
Oxane
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: HMDB0033302)
Cytoplasm (HMDB: HMDB0033302)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033302)

Source

Exogenous

Food

Food (HMDB: HMDB0033302)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB0033302)

Not Available

Nutrient (HMDB: HMDB0033302)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	67 - 70 °C	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	373 g/L	ALOGPS
logP	-0.17	ALOGPS
logP	-0.29	ChemAxon
logS	0.46	ALOGPS
pKa (Strongest Acidic)	14.92	ChemAxon
pKa (Strongest Basic)	-2.8	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	0	ChemAxon
Refractivity	30.8 m³·mol⁻¹	ChemAxon
Polarizability	12.92 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]+	127.427	31661259
DarkChem	[M-H]-	122.131	31661259
DeepCCS	[M+H]+	129.838	30932474
DeepCCS	[M-H]-	127.29	30932474
DeepCCS	[M-2H]-	163.828	30932474
DeepCCS	[M+Na]+	138.471	30932474
AllCCS	[M+H]+	128.3	32859911
AllCCS	[M+H-H2O]+	123.5	32859911
AllCCS	[M+NH4]+	132.7	32859911
AllCCS	[M+Na]+	134.0	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	127.0	32859911
AllCCS	[M+HCOO]-	129.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one	CC1CC(O)CC(=O)O1	2346.1	Standard polar	33892256
(4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one	CC1CC(O)CC(=O)O1	1189.2	Standard non polar	33892256
(4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one	CC1CC(O)CC(=O)O1	1288.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one,1TMS,isomer #1	CC1CC(O[Si](C)(C)C)CC(=O)O1	1314.5	Semi standard non polar	33892256
(4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one,1TBDMS,isomer #1	CC1CC(O[Si](C)(C)C(C)(C)C)CC(=O)O1	1541.0	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 - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-5fdd67b7a2188c9feed5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9600000000-781a4f66429bd12f642c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 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 - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOF	splash10-03e9-4900000000-ff04deeb3b3414756f77	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOF	splash10-03ec-9600000000-da770808e7b6cc187520	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOF	splash10-0006-9000000000-e01ab09bebe8d0f99e95	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOF	splash10-004i-8900000000-997635fe373e196f6b20	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOF	splash10-0006-9100000000-b0c3c3b0a06ad7fcb2c3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOF	splash10-0006-9000000000-e14dffaf886e9321302d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Negative-QTOF	splash10-004i-3900000000-a07bfbf9f10ce929aed2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Negative-QTOF	splash10-052f-9200000000-6c666a98639d052a96dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Negative-QTOF	splash10-0006-9000000000-a96e37173d8847192973	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 10V, Positive-QTOF	splash10-001i-7900000000-7efeadaf25a4685456da	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 20V, Positive-QTOF	splash10-0006-9100000000-8b0eeae6ed8ede94afcd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one 40V, Positive-QTOF	splash10-0006-9000000000-cb0b4a434007a479bf91	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

FDB011326

KNApSAcK ID

Not Available

Chemspider ID

210625

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

241025

PDB ID

Not Available

ChEBI ID

173519

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 (4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one (HMDB0033302)

MOL for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

3D MOL for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

3D SDF for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

3D-SDF for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

PDB for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

3D PDB for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

SMILES for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

INCHI for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

Structure for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

3D Structure for HMDB0033302 ((4S,6S)-3,4,5,6-Tetrahydro-4-hydroxy-6-methyl-2H-pyran-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra