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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:39:40 UTC

Update Date

2022-03-07 02:56:51 UTC

HMDB ID

HMDB0041026

Secondary Accession Numbers

HMDB41026

Metabolite Identification

Common Name

Erinapyrone C

Description

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

Structure

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


  Mrv0541 05061312202D          

 13 14  0  0  0  0            999 V2000
    1.4289   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 12  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041026

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)C12OC1OC(CO)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H10O5/c1-4(10)8-6(11)2-5(3-9)12-7(8)13-8/h2,4,7,9-10H,3H2,1H3

> <INCHI_KEY>
ZXCJKDVKXCEBEI-UHFFFAOYSA-N

> <FORMULA>
C8H10O5

> <MOLECULAR_WEIGHT>
186.162

> <EXACT_MASS>
186.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
17.101529710354242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(1-hydroxyethyl)-3-(hydroxymethyl)-2,7-dioxabicyclo[4.1.0]hept-3-en-5-one

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
-0.7664889833333332

> <ALOGPS_LOGS>
0.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.496184356169802

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.773478892800703

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0749845955255246

> <JCHEM_POLAR_SURFACE_AREA>
79.29

> <JCHEM_REFRACTIVITY>
42.6083

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(1-hydroxyethyl)-3-(hydroxymethyl)-2,7-dioxabicyclo[4.1.0]hept-3-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667  -1.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.897   0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.357   0.206   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    5    6                                                       
CONECT    3    5    9                                                       
CONECT    4    1    8   10                                                  
CONECT    5    2    3   12                                                  
CONECT    6    2    8   11                                                  
CONECT    7    8   12   13                                                  
CONECT    8    4    6    7   13                                             
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    6                                                            
CONECT   12    5    7                                                       
CONECT   13    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5,6-Epoxy-5,6-dihydro-5-(1-hydroxyethyl)-2-(hydroxymethyl)-4H-pyran-4-one	HMDB
6-(1-Hydroxyethyl)-3-(hydroxymethyl)-2,7-dioxabicyclo[4.1.0]hept-3-en-5-one, 9ci	HMDB

Chemical Formula

C₈H₁₀O₅

Average Molecular Weight

186.162

Monoisotopic Molecular Weight

186.05282343

IUPAC Name

6-(1-hydroxyethyl)-3-(hydroxymethyl)-2,7-dioxabicyclo[4.1.0]hept-3-en-5-one

Traditional Name

6-(1-hydroxyethyl)-3-(hydroxymethyl)-2,7-dioxabicyclo[4.1.0]hept-3-en-5-one

CAS Registry Number

157207-53-9

SMILES

CC(O)C12OC1OC(CO)=CC2=O

InChI Identifier

InChI=1S/C8H10O5/c1-4(10)8-6(11)2-5(3-9)12-7(8)13-8/h2,4,7,9-10H,3H2,1H3

InChI Key

ZXCJKDVKXCEBEI-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
Secondary alcohol
Ketone
Oxacycle
Oxirane
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041026)
Cytoplasm (HMDB: HMDB0041026)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041026)

Source

Exogenous

Food

Food (HMDB: HMDB0041026)

Plant (HMDB: HMDB0041026)

Not Available

Nutrient (HMDB: HMDB0041026)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	72 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	35720 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	407 g/L	ALOGPS
logP	-0.92	ALOGPS
logP	-0.77	ChemAxon
logS	0.34	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.61 m³·mol⁻¹	ChemAxon
Polarizability	17.1 Å³	ChemAxon
Number of Rings	2	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]+	143.335	31661259
DarkChem	[M-H]-	137.195	31661259
DeepCCS	[M-2H]-	176.132	30932474
DeepCCS	[M+Na]+	151.585	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.3	32859911
AllCCS	[M+NH4]+	143.5	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	137.7	32859911
AllCCS	[M+Na-2H]-	138.1	32859911
AllCCS	[M+HCOO]-	138.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Erinapyrone C	CC(O)C12OC1OC(CO)=CC2=O	2827.0	Standard polar	33892256
Erinapyrone C	CC(O)C12OC1OC(CO)=CC2=O	1531.6	Standard non polar	33892256
Erinapyrone C	CC(O)C12OC1OC(CO)=CC2=O	1668.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Erinapyrone C,1TMS,isomer #1	CC(O[Si](C)(C)C)C12OC1OC(CO)=CC2=O	1624.3	Semi standard non polar	33892256
Erinapyrone C,1TMS,isomer #2	CC(O)C12OC1OC(CO[Si](C)(C)C)=CC2=O	1707.1	Semi standard non polar	33892256
Erinapyrone C,2TMS,isomer #1	CC(O[Si](C)(C)C)C12OC1OC(CO[Si](C)(C)C)=CC2=O	1734.3	Semi standard non polar	33892256
Erinapyrone C,1TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C12OC1OC(CO)=CC2=O	1874.3	Semi standard non polar	33892256
Erinapyrone C,1TBDMS,isomer #2	CC(O)C12OC1OC(CO[Si](C)(C)C(C)(C)C)=CC2=O	1928.3	Semi standard non polar	33892256
Erinapyrone C,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)C12OC1OC(CO[Si](C)(C)C(C)(C)C)=CC2=O	2171.7	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 - Erinapyrone C GC-MS (Non-derivatized) - 70eV, Positive	splash10-0037-9200000000-11b737848e448aa656ab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinapyrone C GC-MS (2 TMS) - 70eV, Positive	splash10-014i-6910000000-76c33542dec6de264ce1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinapyrone C GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Erinapyrone C 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 C 10V, Positive-QTOF	splash10-00kr-0900000000-8eb4959584dccba06437	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 20V, Positive-QTOF	splash10-0170-1900000000-8268c4075ee5a61f5826	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 40V, Positive-QTOF	splash10-0zfr-9200000000-56b89d8b63d51944dd89	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 10V, Negative-QTOF	splash10-000i-0900000000-cfb9e4a6dd558e1e895d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 20V, Negative-QTOF	splash10-00kr-5900000000-c3aee9556bc774a7f073	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 40V, Negative-QTOF	splash10-0zpl-9000000000-f08f3c09f7a97f01d489	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 10V, Positive-QTOF	splash10-000i-0900000000-f7de337e0f10125e1643	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 20V, Positive-QTOF	splash10-000i-7900000000-0023206a046ffb6e6763	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 40V, Positive-QTOF	splash10-014s-9400000000-04daba349a77255eb2a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 10V, Negative-QTOF	splash10-000i-0900000000-cdeaf8800706cb67c648	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 20V, Negative-QTOF	splash10-0076-3900000000-626b8b860a451bb14de9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Erinapyrone C 40V, Negative-QTOF	splash10-00kf-9200000000-44e6494163f35adbf602	2021-09-23	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

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

FDB020895

KNApSAcK ID

C00024010

Chemspider ID

28534154

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85125837

PDB ID

Not Available

ChEBI ID

168041

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1888801

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 C (HMDB0041026)

MOL for HMDB0041026 (Erinapyrone C)

3D MOL for HMDB0041026 (Erinapyrone C)

3D SDF for HMDB0041026 (Erinapyrone C)

3D-SDF for HMDB0041026 (Erinapyrone C)

PDB for HMDB0041026 (Erinapyrone C)

3D PDB for HMDB0041026 (Erinapyrone C)

SMILES for HMDB0041026 (Erinapyrone C)

INCHI for HMDB0041026 (Erinapyrone C)

Structure for HMDB0041026 (Erinapyrone C)

3D Structure for HMDB0041026 (Erinapyrone C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra