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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:06:45 UTC

Update Date

2023-02-21 17:28:42 UTC

HMDB ID

HMDB0041427

Secondary Accession Numbers

HMDB41427

Metabolite Identification

Common Name

Erinapyrone B

Description

Erinapyrone B 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. Erinapyrone B has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make erinapyrone b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Erinapyrone B.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R)-2,3-dihydro-2-Hydroxymethyl-6-methyl-4H-pyran-4-one	HMDB

Chemical Formula

C₇H₁₀O₃

Average Molecular Weight

142.1525

Monoisotopic Molecular Weight

142.062994186

IUPAC Name

2-(hydroxymethyl)-6-methyl-3,4-dihydro-2H-pyran-4-one

Traditional Name

2-(hydroxymethyl)-6-methyl-2,3-dihydropyran-4-one

CAS Registry Number

146064-67-7

SMILES

CC1=CC(=O)CC(CO)O1

InChI Identifier

InChI=1S/C7H10O3/c1-5-2-6(9)3-7(4-8)10-5/h2,7-8H,3-4H2,1H3

InChI Key

ULVSURGNEAHOBK-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
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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: HMDB0041427)
Cytoplasm (HMDB: HMDB0041427)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041427)

Source

Exogenous

Food

Food (HMDB: HMDB0041427)

Plant (HMDB: HMDB0041427)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041427)

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	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	137 g/L	ALOGPS
logP	-0.63	ALOGPS
logP	-0.23	ChemAxon
logS	-0.02	ALOGPS
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.49 m³·mol⁻¹	ChemAxon
Polarizability	14.48 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]+	132.313	31661259
DarkChem	[M-H]-	128.408	31661259
DeepCCS	[M+H]+	143.18	30932474
DeepCCS	[M-H]-	140.254	30932474
DeepCCS	[M-2H]-	176.632	30932474
DeepCCS	[M+Na]+	151.988	30932474
AllCCS	[M+H]+	129.7	32859911
AllCCS	[M+H-H2O]+	125.0	32859911
AllCCS	[M+NH4]+	134.1	32859911
AllCCS	[M+Na]+	135.4	32859911
AllCCS	[M-H]-	128.1	32859911
AllCCS	[M+Na-2H]-	129.8	32859911
AllCCS	[M+HCOO]-	131.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erinapyrone B	CC1=CC(=O)CC(CO)O1	2369.2	Standard polar	33892256
Erinapyrone B	CC1=CC(=O)CC(CO)O1	1222.8	Standard non polar	33892256
Erinapyrone B	CC1=CC(=O)CC(CO)O1	1299.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erinapyrone B,1TMS,isomer #1	CC1=CC(=O)CC(CO[Si](C)(C)C)O1	1442.7	Semi standard non polar	33892256
Erinapyrone B,1TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=CC(CO)O1	1464.7	Semi standard non polar	33892256
Erinapyrone B,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(CO[Si](C)(C)C)O1	1529.5	Semi standard non polar	33892256
Erinapyrone B,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(CO[Si](C)(C)C)O1	1535.3	Standard non polar	33892256
Erinapyrone B,1TBDMS,isomer #1	CC1=CC(=O)CC(CO[Si](C)(C)C(C)(C)C)O1	1689.7	Semi standard non polar	33892256
Erinapyrone B,1TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(CO)O1	1690.7	Semi standard non polar	33892256
Erinapyrone B,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(CO[Si](C)(C)C(C)(C)C)O1	1959.9	Semi standard non polar	33892256
Erinapyrone B,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(CO[Si](C)(C)C(C)(C)C)O1	1970.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Erinapyrone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9400000000-b3b21030a9d999da9732	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinapyrone B GC-MS (1 TMS) - 70eV, Positive	splash10-0g4l-9500000000-7b9dd4cbac8e15079947	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinapyrone B 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 - Erinapyrone B 10V, Positive-QTOF	splash10-0006-0900000000-509a1d57dab0c31ce470	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 20V, Positive-QTOF	splash10-002f-9800000000-1613ad98c5329fda5a9b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 40V, Positive-QTOF	splash10-00lu-9000000000-0615bef6940a9f49310c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 10V, Negative-QTOF	splash10-0006-0900000000-7857d9009b5fa8cef44e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 20V, Negative-QTOF	splash10-0007-6900000000-616994e952e930d01213	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 40V, Negative-QTOF	splash10-0a59-9000000000-c16e4028f68d15c5859d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 10V, Negative-QTOF	splash10-0006-9800000000-c127202adb3b6f3ce336	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 20V, Negative-QTOF	splash10-05fu-9700000000-a1d8ffec8627cea17713	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 40V, Negative-QTOF	splash10-05mo-9000000000-efe90817118a76c20a68	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 10V, Positive-QTOF	splash10-002f-4900000000-d668c84ef413c23cbaf1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 20V, Positive-QTOF	splash10-000x-9100000000-ea6cc1d713af61af9bef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone B 40V, Positive-QTOF	splash10-0006-9000000000-a8b7a1fd4147c5c327a9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB021376

KNApSAcK ID

C00024009

Chemspider ID

35015183

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85092481

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1892331

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 Erinapyrone B (HMDB0041427)

MOL for HMDB0041427 (Erinapyrone B)

3D MOL for HMDB0041427 (Erinapyrone B)

3D SDF for HMDB0041427 (Erinapyrone B)

3D-SDF for HMDB0041427 (Erinapyrone B)

PDB for HMDB0041427 (Erinapyrone B)

3D PDB for HMDB0041427 (Erinapyrone B)

SMILES for HMDB0041427 (Erinapyrone B)

INCHI for HMDB0041427 (Erinapyrone B)

Structure for HMDB0041427 (Erinapyrone B)

3D Structure for HMDB0041427 (Erinapyrone B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra