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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:06:11 UTC

Update Date

2023-02-21 17:26:43 UTC

HMDB ID

HMDB0038760

Secondary Accession Numbers

HMDB38760

Metabolite Identification

Common Name

Herierin III

Description

Herierin III belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Herierin III 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 herierin III a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Herierin III.

Structure

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

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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667  -3.080   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       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6    8                                                       
CONECT    3    6    9                                                       
CONECT    4    7   10                                                       
CONECT    5    1    7   12                                                  
CONECT    6    2    3   12                                                  
CONECT    7    4    5    8                                                  
CONECT    8    2    7   11                                                  
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    8                                                            
CONECT   12    5    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,6-Bis(hydroxymethyl)-2-methyl-4H-pyran-4-one	HMDB
6-Methyl-2,5-dihydroxymethyl-gamma pyranone	HMDB, MeSH
6-Methyl-2,5-dihydroxymethyl-gamma-pyranone III	HMDB
Herierin III	MeSH

Chemical Formula

C₈H₁₀O₄

Average Molecular Weight

170.1626

Monoisotopic Molecular Weight

170.057908808

IUPAC Name

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

Traditional Name

3,6-bis(hydroxymethyl)-2-methylpyran-4-one

CAS Registry Number

131123-56-3

SMILES

CC1=C(CO)C(=O)C=C(CO)O1

InChI Identifier

InChI=1S/C8H10O4/c1-5-7(4-10)8(11)2-6(3-9)12-5/h2,9-10H,3-4H2,1H3

InChI Key

FEEAMUNPZANTSE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Cyclic ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038760)
Cytoplasm (HMDB: HMDB0038760)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038760)

Source

Exogenous

Exogenous (HMDB: HMDB0038760)

Food

Food (HMDB: HMDB0038760)

Plant (HMDB: HMDB0038760)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038760)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	122 - 123 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	262000 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	15.5 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-0.94	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	14.24	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.25 m³·mol⁻¹	ChemAxon
Polarizability	16.78 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]+	138.244	31661259
DarkChem	[M-H]-	133.918	31661259
DeepCCS	[M+H]+	148.508	30932474
DeepCCS	[M-H]-	145.851	30932474
DeepCCS	[M-2H]-	181.816	30932474
DeepCCS	[M+Na]+	157.321	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	131.0	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.8	32859911
AllCCS	[M-H]-	134.9	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	137.3	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. Predicted by Afia on May 17, 2022.	2.61 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3804 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	55.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	480.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	293.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	44.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	231.1 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	285.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	426.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	617.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	113.2 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	964.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	192.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	503.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	265.8 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	235.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Herierin III	CC1=C(CO)C(=O)C=C(CO)O1	2331.1	Standard polar	33892256
Herierin III	CC1=C(CO)C(=O)C=C(CO)O1	1544.2	Standard non polar	33892256
Herierin III	CC1=C(CO)C(=O)C=C(CO)O1	1736.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Herierin III,1TMS,isomer #1	CC1=C(CO[Si](C)(C)C)C(=O)C=C(CO)O1	1642.6	Semi standard non polar	33892256
Herierin III,1TMS,isomer #2	CC1=C(CO)C(=O)C=C(CO[Si](C)(C)C)O1	1637.6	Semi standard non polar	33892256
Herierin III,2TMS,isomer #1	CC1=C(CO[Si](C)(C)C)C(=O)C=C(CO[Si](C)(C)C)O1	1739.2	Semi standard non polar	33892256
Herierin III,1TBDMS,isomer #1	CC1=C(CO[Si](C)(C)C(C)(C)C)C(=O)C=C(CO)O1	1916.0	Semi standard non polar	33892256
Herierin III,1TBDMS,isomer #2	CC1=C(CO)C(=O)C=C(CO[Si](C)(C)C(C)(C)C)O1	1891.3	Semi standard non polar	33892256
Herierin III,2TBDMS,isomer #1	CC1=C(CO[Si](C)(C)C(C)(C)C)C(=O)C=C(CO[Si](C)(C)C(C)(C)C)O1	2204.7	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 - Herierin III GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udu-3900000000-3f5827154f03bf60f991	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Herierin III GC-MS (2 TMS) - 70eV, Positive	splash10-00ba-6291000000-f6cf84ce5688c029d356	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Herierin III GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Herierin III 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 - Herierin III 10V, Positive-QTOF	splash10-0uk9-0900000000-262f1e4a8ed1badb373a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 20V, Positive-QTOF	splash10-0udi-0900000000-556dd73ddad8e493c6a2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 40V, Positive-QTOF	splash10-000b-9700000000-af28bb34dcd068ca899f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 10V, Negative-QTOF	splash10-014i-0900000000-8c0c570455e65db710df	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 20V, Negative-QTOF	splash10-000i-3900000000-d8110e6d96df47390763	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 40V, Negative-QTOF	splash10-01u3-9300000000-9fd40bc854a6ab9b83bd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 10V, Positive-QTOF	splash10-0fk9-0900000000-92b03b7e48de0e281995	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 20V, Positive-QTOF	splash10-00fr-0900000000-5098725fa0d17733e6d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 40V, Positive-QTOF	splash10-00di-9500000000-5ac2f48fc8fc788908a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 10V, Negative-QTOF	splash10-01b9-0900000000-41c7f3e9dd4cccdd5ac2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 20V, Negative-QTOF	splash10-059i-1900000000-b42f5ff08f2941517ac4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Herierin III 40V, Negative-QTOF	splash10-00kf-9100000000-151dbdbf2472d7f57f58	2021-09-23	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

FDB018177

KNApSAcK ID

C00055142

Chemspider ID

116105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131340

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1871061

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 Herierin III (HMDB0038760)

MOL for HMDB0038760 (Herierin III)

3D MOL for HMDB0038760 (Herierin III)

3D SDF for HMDB0038760 (Herierin III)

3D-SDF for HMDB0038760 (Herierin III)

PDB for HMDB0038760 (Herierin III)

3D PDB for HMDB0038760 (Herierin III)

SMILES for HMDB0038760 (Herierin III)

INCHI for HMDB0038760 (Herierin III)

Structure for HMDB0038760 (Herierin III)

3D Structure for HMDB0038760 (Herierin III)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra