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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:20:26 UTC

Update Date

2021-09-26 23:11:30 UTC

HMDB ID

HMDB0256081

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Paeonol

Description

Paeonol belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on Paeonol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Paeonol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Paeonol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      27.323 -18.741   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.323 -20.281   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.661 -21.055   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.991 -20.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.991 -18.741   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.661 -17.975   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.663 -16.435   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.999 -15.663   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      27.329 -15.660   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      31.319 -17.976   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      28.663 -22.595   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      27.329 -23.363   0.000  0.00  0.00           C+0
CONECT    1    6    2                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5   10    4    6                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5                                                            
CONECT   11    3   12                                                       
CONECT   12   11                                                            
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
2-Hydroxy-4-methoxyacetophenone	MeSH
Peonol	MeSH

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

1-(2-hydroxy-4-methoxyphenyl)ethan-1-one

Traditional Name

paeonol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C(C)=O)C(O)=C1

InChI Identifier

InChI=1S/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3

InChI Key

UILPJVPSNHJFIK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Methoxyphenol
Acetophenone
Phenoxy compound
Anisole
Benzoyl
Phenol ether
Aryl alkyl ketone
Methoxybenzene
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ether
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:69581 )
methoxybenzene (CHEBI:69581 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	1.6	ALOGPS
logP	1.72	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.05	ChemAxon
pKa (Strongest Basic)	-4	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	2	ChemAxon
Refractivity	44.9 m³·mol⁻¹	ChemAxon
Polarizability	16.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	136.143	30932474
DeepCCS	[M-H]-	132.562	30932474
DeepCCS	[M-2H]-	170.131	30932474
DeepCCS	[M+Na]+	145.67	30932474
AllCCS	[M+H]+	135.2	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.5	32859911
AllCCS	[M-H]-	134.8	32859911
AllCCS	[M+Na-2H]-	136.0	32859911
AllCCS	[M+HCOO]-	137.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Paeonol	COC1=CC=C(C(C)=O)C(O)=C1	2267.4	Standard polar	33892256
Paeonol	COC1=CC=C(C(C)=O)C(O)=C1	1424.2	Standard non polar	33892256
Paeonol	COC1=CC=C(C(C)=O)C(O)=C1	1437.8	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 - Paeonol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0v4i-2900000000-e4764cf32031039d4511	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paeonol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paeonol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Paeonol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 10V, Positive-QTOF	splash10-014i-0900000000-3e957a482a54e9cd2d2c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 10V, Positive-QTOF	splash10-014i-0900000000-a3da6add4b091c3bc9dc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 30V, Positive-QTOF	splash10-00di-5900000000-32be561bc5ab4eca8a0e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 50V, Positive-QTOF	splash10-01b9-0900000000-508c4c16e784425fb0ae	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 6V, Positive-QTOF	splash10-014i-0900000000-1002ce1e2e6c7666b8f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 10V, Positive-QTOF	splash10-014i-0900000000-475183ddb5788d8dce9d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 10V, Positive-QTOF	splash10-014i-0900000000-8ac85a2e0d7b6703b90e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 10V, Positive-QTOF	splash10-014i-0900000000-3906f130517481eaa76c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 30V, Positive-QTOF	splash10-00di-2900000000-05f856ba720ee64b67fe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 30V, Positive-QTOF	splash10-00xr-2900000000-a14e7fc11f450d2925dd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 50V, Positive-QTOF	splash10-014i-7900000000-1706606f93ffdb90fbf2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 50V, Positive-QTOF	splash10-014i-1900000000-72bf3951ee85cea5241b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Paeonol 10V, Positive-QTOF	splash10-014i-0900000000-cd8601c7a793881c44ad	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paeonol 10V, Positive-QTOF	splash10-014i-0900000000-c2dda62458d2190670ad	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paeonol 20V, Positive-QTOF	splash10-014i-0900000000-11476f561b8a54861849	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paeonol 40V, Positive-QTOF	splash10-0gbc-5900000000-ec6f9dbbf8d019cde306	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paeonol 10V, Negative-QTOF	splash10-014i-0900000000-f5980f963b64c5b25faa	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paeonol 20V, Negative-QTOF	splash10-014i-0900000000-9035c9433a6a1f7ddf48	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Paeonol 40V, Negative-QTOF	splash10-000x-9400000000-4273604ebef84703d875	2017-06-28	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Paeonol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1102121

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Paeonol (HMDB0256081)

MOL for HMDB0256081 (Paeonol)

3D MOL for HMDB0256081 (Paeonol)

3D SDF for HMDB0256081 (Paeonol)

3D-SDF for HMDB0256081 (Paeonol)

PDB for HMDB0256081 (Paeonol)

3D PDB for HMDB0256081 (Paeonol)

SMILES for HMDB0256081 (Paeonol)

INCHI for HMDB0256081 (Paeonol)

Structure for HMDB0256081 (Paeonol)

3D Structure for HMDB0256081 (Paeonol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra