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

2012-09-12 03:06:42 UTC

Update Date

2023-02-21 17:28:41 UTC

HMDB ID

HMDB0041426

Secondary Accession Numbers

HMDB41426

Metabolite Identification

Common Name

Erinapyrone A

Description

Erinapyrone A 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 A 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 a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Erinapyrone A.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

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

Chemical Formula

C₇H₁₀O₃

Average Molecular Weight

142.1525

Monoisotopic Molecular Weight

142.062994186

IUPAC Name

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

Traditional Name

2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one

CAS Registry Number

146064-66-6

SMILES

CC1CC(=O)C=C(CO)O1

InChI Identifier

InChI=1S/C7H10O3/c1-5-2-6(9)3-7(4-8)10-5/h3,5,8H,2,4H2,1H3

InChI Key

FXGUGSUNHREWBM-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: HMDB0041426)
Cytoplasm (HMDB: HMDB0041426)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041426)

Source

Exogenous

Food

Food (HMDB: HMDB0041426)

Plant (HMDB: HMDB0041426)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041426)

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	119 g/L	ALOGPS
logP	-0.38	ALOGPS
logP	-0.23	ChemAxon
logS	-0.08	ALOGPS
pKa (Strongest Acidic)	14.38	ChemAxon
pKa (Strongest Basic)	-3.1	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	14.47 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]+	131.65	31661259
DarkChem	[M-H]-	129.031	31661259
DeepCCS	[M+H]+	140.89	30932474
DeepCCS	[M-H]-	137.937	30932474
DeepCCS	[M-2H]-	174.569	30932474
DeepCCS	[M+Na]+	149.764	30932474
AllCCS	[M+H]+	129.6	32859911
AllCCS	[M+H-H2O]+	124.9	32859911
AllCCS	[M+NH4]+	134.0	32859911
AllCCS	[M+Na]+	135.2	32859911
AllCCS	[M-H]-	127.8	32859911
AllCCS	[M+Na-2H]-	129.5	32859911
AllCCS	[M+HCOO]-	131.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erinapyrone A	CC1CC(=O)C=C(CO)O1	2394.5	Standard polar	33892256
Erinapyrone A	CC1CC(=O)C=C(CO)O1	1209.8	Standard non polar	33892256
Erinapyrone A	CC1CC(=O)C=C(CO)O1	1305.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erinapyrone A,1TMS,isomer #1	CC1CC(=O)C=C(CO[Si](C)(C)C)O1	1422.6	Semi standard non polar	33892256
Erinapyrone A,1TMS,isomer #2	CC1C=C(O[Si](C)(C)C)C=C(CO)O1	1410.6	Semi standard non polar	33892256
Erinapyrone A,2TMS,isomer #1	CC1C=C(O[Si](C)(C)C)C=C(CO[Si](C)(C)C)O1	1513.8	Semi standard non polar	33892256
Erinapyrone A,2TMS,isomer #1	CC1C=C(O[Si](C)(C)C)C=C(CO[Si](C)(C)C)O1	1526.0	Standard non polar	33892256
Erinapyrone A,1TBDMS,isomer #1	CC1CC(=O)C=C(CO[Si](C)(C)C(C)(C)C)O1	1661.5	Semi standard non polar	33892256
Erinapyrone A,1TBDMS,isomer #2	CC1C=C(O[Si](C)(C)C(C)(C)C)C=C(CO)O1	1664.6	Semi standard non polar	33892256
Erinapyrone A,2TBDMS,isomer #1	CC1C=C(O[Si](C)(C)C(C)(C)C)C=C(CO[Si](C)(C)C(C)(C)C)O1	1921.2	Semi standard non polar	33892256
Erinapyrone A,2TBDMS,isomer #1	CC1C=C(O[Si](C)(C)C(C)(C)C)C=C(CO[Si](C)(C)C(C)(C)C)O1	1948.5	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 A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f97-9400000000-5410d7f5551401a5fc6d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinapyrone A GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9700000000-a482a31248b201806da7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinapyrone 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 - Erinapyrone A 10V, Positive-QTOF	splash10-0006-0900000000-0556be5cddedf972a655	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 20V, Positive-QTOF	splash10-00nf-9400000000-494176c1eea3f07b342d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 40V, Positive-QTOF	splash10-015c-9000000000-9cf96962b35bd0adc02c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 10V, Negative-QTOF	splash10-0006-0900000000-07624982cfceaf34d468	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 20V, Negative-QTOF	splash10-06xx-2900000000-368b72c0bf47535df534	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 40V, Negative-QTOF	splash10-0a4l-9000000000-457f598b5c0230119f3e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 10V, Negative-QTOF	splash10-03dl-2900000000-433acf6915a9d1491d08	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 20V, Negative-QTOF	splash10-06xx-9600000000-377210ea5c69675c234b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 40V, Negative-QTOF	splash10-05mo-9100000000-9dd5c3988140c158e1e9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 10V, Positive-QTOF	splash10-004i-2900000000-f62bf13b1a22be4d6859	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 20V, Positive-QTOF	splash10-000x-9200000000-de80a5c45b4f5d2b3a33	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone A 40V, Positive-QTOF	splash10-0006-9000000000-4b983aa2eeb776799334	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, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

FDB021375

KNApSAcK ID

C00024008

Chemspider ID

24189708

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45083461

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1892321

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 A (HMDB0041426)

MOL for HMDB0041426 (Erinapyrone A)

3D MOL for HMDB0041426 (Erinapyrone A)

3D SDF for HMDB0041426 (Erinapyrone A)

3D-SDF for HMDB0041426 (Erinapyrone A)

PDB for HMDB0041426 (Erinapyrone A)

3D PDB for HMDB0041426 (Erinapyrone A)

SMILES for HMDB0041426 (Erinapyrone A)

INCHI for HMDB0041426 (Erinapyrone A)

Structure for HMDB0041426 (Erinapyrone A)

3D Structure for HMDB0041426 (Erinapyrone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra