Jump To Section:

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 21:31:06 UTC

Update Date

2023-02-21 17:25:20 UTC

HMDB ID

HMDB0036380

Secondary Accession Numbers

HMDB36380

Metabolite Identification

Common Name

xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Description

xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Based on a literature review very few articles have been published on xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-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

C₇H₁₀O₄

Average Molecular Weight

158.1519

Monoisotopic Molecular Weight

158.057908808

IUPAC Name

3-hydroxy-5-methoxy-6-methyl-3,4-dihydro-2H-pyran-4-one

Traditional Name

5-hydroxy-3-methoxy-2-methyl-5,6-dihydropyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(C)OCC(O)C1=O

InChI Identifier

InChI=1S/C7H10O4/c1-4-7(10-2)6(9)5(8)3-11-4/h5,8H,3H2,1-2H3

InChI Key

JOWYHBUWSWRYOG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Vinylogous ester
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
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: HMDB0036380)
Cytoplasm (HMDB: HMDB0036380)

Source

Exogenous

Exogenous (HMDB: HMDB0036380)

Food

Food (HMDB: HMDB0036380)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036380)

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	350 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.73	ChemAxon
logS	0.34	ALOGPS
pKa (Strongest Acidic)	12.51	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.59 m³·mol⁻¹	ChemAxon
Polarizability	15.08 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]+	135.402	31661259
DarkChem	[M-H]-	132.261	31661259
DeepCCS	[M+H]+	134.932	30932474
DeepCCS	[M-H]-	131.155	30932474
DeepCCS	[M-2H]-	168.369	30932474
DeepCCS	[M+Na]+	143.671	30932474
AllCCS	[M+H]+	133.7	32859911
AllCCS	[M+H-H2O]+	129.1	32859911
AllCCS	[M+NH4]+	137.9	32859911
AllCCS	[M+Na]+	139.1	32859911
AllCCS	[M-H]-	130.2	32859911
AllCCS	[M+Na-2H]-	131.6	32859911
AllCCS	[M+HCOO]-	133.2	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.	2.6 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2301 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.87 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1469.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	332.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	111.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	52.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	394.8 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	414.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	788.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	316.2 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	1097.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	302.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	410.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	240.8 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	100.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one	COC1=C(C)OCC(O)C1=O	2009.4	Standard polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one	COC1=C(C)OCC(O)C1=O	1240.1	Standard non polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one	COC1=C(C)OCC(O)C1=O	1243.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one,1TMS,isomer #1	COC1=C(C)OCC(O[Si](C)(C)C)C1=O	1351.7	Semi standard non polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one,1TMS,isomer #2	COC1=C(C)OCC(O)=C1O[Si](C)(C)C	1356.0	Semi standard non polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one,2TMS,isomer #1	COC1=C(C)OCC(O[Si](C)(C)C)=C1O[Si](C)(C)C	1460.7	Semi standard non polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one,2TMS,isomer #1	COC1=C(C)OCC(O[Si](C)(C)C)=C1O[Si](C)(C)C	1540.8	Standard non polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one,1TBDMS,isomer #1	COC1=C(C)OCC(O[Si](C)(C)C(C)(C)C)C1=O	1606.7	Semi standard non polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one,1TBDMS,isomer #2	COC1=C(C)OCC(O)=C1O[Si](C)(C)C(C)(C)C	1641.9	Semi standard non polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one,2TBDMS,isomer #1	COC1=C(C)OCC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	1980.7	Semi standard non polar	33892256
xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one,2TBDMS,isomer #1	COC1=C(C)OCC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	1964.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dj-9300000000-26fc8c5a18c34598d32a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one GC-MS (1 TMS) - 70eV, Positive	splash10-00xs-9210000000-4b9973ef8f458af8c732	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-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 - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 10V, Positive-QTOF	splash10-0a4i-0900000000-754b7e79169b111af957	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 20V, Positive-QTOF	splash10-0a4l-1900000000-e6cb9dfbb3cd9069154a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 40V, Positive-QTOF	splash10-0btc-9200000000-fc9674e00506fa42fcf3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 10V, Negative-QTOF	splash10-0a4i-1900000000-f74ab181e89f4f92a8f3	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 20V, Negative-QTOF	splash10-0a4i-5900000000-fc950e4107a032bfedab	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 40V, Negative-QTOF	splash10-0006-9000000000-d1d5636cb40d86cbbfb1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 10V, Negative-QTOF	splash10-0a4i-1900000000-d225f02558408035b3d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 20V, Negative-QTOF	splash10-0a6u-6900000000-f350206e5052de071745	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 40V, Negative-QTOF	splash10-05mo-9200000000-b0b3e216eafb6141c778	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 10V, Positive-QTOF	splash10-0a4l-0900000000-deec679865241f72a4af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 20V, Positive-QTOF	splash10-05mp-9500000000-dbdeb4f53b324cb99a63	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one 40V, Positive-QTOF	splash10-0kfw-9000000000-b871619975c1f5ef50ca	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

FDB015258

KNApSAcK ID

Not Available

Chemspider ID

35014133

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15114468

PDB ID

Not Available

ChEBI ID

168562

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 xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (HMDB0036380)

MOL for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

3D MOL for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

3D SDF for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

3D-SDF for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

PDB for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

3D PDB for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

SMILES for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

INCHI for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

Structure for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

3D Structure for HMDB0036380 (xi-2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra