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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:58:12 UTC

Update Date

2021-09-26 22:52:52 UTC

HMDB ID

HMDB0244840

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-

Description

2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-, also known as mevalonolactone, belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Thus, 2H-pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- is considered to be a fatty ester. Based on a literature review very few articles have been published on 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2h-pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (r)- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Mevalonolactone	HMDB
Mevalonic acid lactone	HMDB
Mevalonolactone, (S)-isomer	HMDB
Mevalonolactone, (R)-isomer	HMDB
Mevalonolactone, 3-(14)C-labeled	HMDB
Mevalonolactone, (+-)-isomer	HMDB

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.143

Monoisotopic Molecular Weight

130.062994182

IUPAC Name

4-hydroxy-4-methyloxan-2-one

Traditional Name

4-hydroxy-4-methyloxan-2-one

CAS Registry Number

Not Available

SMILES

CC1(O)CCOC(=O)C1

InChI Identifier

InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3

InChI Key

JYVXNLLUYHCIIH-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
Tertiary 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

Lactones (LMFA07040003 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	-0.14	ALOGPS
logP	-0.43	ChemAxon
logS	0.38	ALOGPS
pKa (Strongest Acidic)	14.71	ChemAxon
pKa (Strongest Basic)	-2.9	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	31.02 m³·mol⁻¹	ChemAxon
Polarizability	12.75 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
DeepCCS	[M+H]+	129.584	30932474
DeepCCS	[M-H]-	126.622	30932474
DeepCCS	[M-2H]-	163.527	30932474
DeepCCS	[M+Na]+	138.514	30932474
AllCCS	[M+H]+	125.9	32859911
AllCCS	[M+H-H2O]+	121.1	32859911
AllCCS	[M+NH4]+	130.3	32859911
AllCCS	[M+Na]+	131.6	32859911
AllCCS	[M-H]-	124.9	32859911
AllCCS	[M+Na-2H]-	127.1	32859911
AllCCS	[M+HCOO]-	129.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	9.2866 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1250.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	310.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	106.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	327.2 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	396.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	94.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	682.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	205.3 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	909.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	235.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	240.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	466.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	266.6 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	208.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-	CC1(O)CCOC(=O)C1	2185.3	Standard polar	33892256
2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-	CC1(O)CCOC(=O)C1	1148.9	Standard non polar	33892256
2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-	CC1(O)CCOC(=O)C1	1283.8	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 - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adl-9100000000-1c9a26b68d29653e0012	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 10V, Positive-QTOF	splash10-01bc-9100000000-56ed18633cb5012d64db	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 20V, Positive-QTOF	splash10-0006-9000000000-86bbbab559d82135dd17	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 35V, Positive-QTOF	splash10-014i-9300000000-9a2e00e5dec1a6784bd1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 40V, Positive-QTOF	splash10-0006-9000000000-f4658064cfb9d6dc2737	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 35V, Positive-QTOF	splash10-014i-9300000000-4a8a574b5f19550a135d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 10V, Positive-QTOF	splash10-03di-2900000000-350c680f97580a3bcd72	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 20V, Positive-QTOF	splash10-0jbm-9200000000-53d741ed76e6bdf9342f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 40V, Positive-QTOF	splash10-0006-9000000000-1fa9b1e3048c34d9c1fc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 10V, Negative-QTOF	splash10-004i-5900000000-34b2add939c12cfa98dd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 20V, Negative-QTOF	splash10-01ox-9400000000-8b6184467b21550de12d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- 40V, Negative-QTOF	splash10-052f-9000000000-f91715bf1f16241894b8	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9999

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10428

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)- (HMDB0244840)

MOL for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

3D MOL for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

3D SDF for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

3D-SDF for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

PDB for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

3D PDB for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

SMILES for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

INCHI for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

Structure for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

3D Structure for HMDB0244840 (2H-Pyran-2-one, tetrahydro-4-hydroxy-4-methyl-, (R)-)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra