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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 01:04:15 UTC

Update Date

2021-09-26 22:57:51 UTC

HMDB ID

HMDB0247918

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acetovanillone

Description

Acetovanillone, also known as acetoguaiacon or apocynine, 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. Acetovanillone is a faint, sweet, and vanillin tasting compound. Acetovanillone is found, on average, in the highest concentration within white wine. Acetovanillone has also been detected, but not quantified in, a few different foods, such as asparagus (Asparagus officinalis), corns (Zea mays), and garden onions (Allium cepa). This could make acetovanillone a potential biomarker for the consumption of these foods. Acetovanillone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Acetovanillone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Acetovanillone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Acetovanillone 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-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8609.7168608.509   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8615.0448611.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8616.3738610.813   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8615.0448613.118   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8613.7168610.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8612.3838611.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8611.0498610.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8611.0498609.275   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8612.3828608.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8613.7168609.275   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8612.3828606.969   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8613.7128606.202   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    3    4    5                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    1                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   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
1-(4-Hydroxy-3-methoxyphenyl)ethanone	ChEBI
4'-Hydroxy-3'-methoxyacetophenone	ChEBI
4-Acetyl-2-methoxyphenol	ChEBI
4-Hydroxy-3-methoxyphenyl methyl ketone	ChEBI
Acetoguaiacon	ChEBI
Acetoguaiacone	ChEBI
4-Hydroxy-3-methoxyacetophenone	HMDB
Apocynine	HMDB
Apocynin	HMDB
2-Methoxy-4-acetylphenol	HMDB
3-Methoxy-4-hydroxyphenylethanone	HMDB
3'-Methoxy-4'-hydroxyacetophenone	HMDB
3’-methoxy-4’-hydroxyacetophenone	HMDB
4-Acetylguaiacol	HMDB
4’-hydroxy-3’-methoxyacetophenone	HMDB
Acetoguaiacol	HMDB
Acetoguaicone	HMDB
Acetovanillone	ChEBI

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

Traditional Name

apocynin

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(C)=O

InChI Identifier

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

InChI Key

DFYRUELUNQRZTB-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
Methoxybenzene
Aryl alkyl ketone
Anisole
Phenol ether
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Ether
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methyl ketone (CHEBI:2781 )
aromatic ketone (CHEBI:2781 )
acetophenones (CHEBI:2781 )
Flavans, Flavanols and Leucoanthocyanidins (C11380 )

Ontology

Sweet

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0247918)

Food

Beverage

Fermented beverage

White wine (FooDB: FOOD00917)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Not Available

EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor (HMDB: HMDB0247918)

Enzyme inhibitor

NADPH-oxidase inhibitor (HMDB: HMDB0247918)

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	1.62	ALOGPS
logP	1.07	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	8.27	ChemAxon
pKa (Strongest Basic)	-4.9	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	16.94 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]+	136.089	30932474
DeepCCS	[M-H]-	132.926	30932474
DeepCCS	[M-2H]-	169.867	30932474
DeepCCS	[M+Na]+	145.128	30932474
AllCCS	[M+H]+	134.8	32859911
AllCCS	[M+H-H2O]+	130.4	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	133.8	32859911
AllCCS	[M+Na-2H]-	134.9	32859911
AllCCS	[M+HCOO]-	136.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.5196 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1532.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	332.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	121.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	366.2 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	400.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	848.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	330.4 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	1001.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	285.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	427.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	302.4 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	111.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetovanillone	COC1=CC(=CC=C1O)C(C)=O	2495.9	Standard polar	33892256
Acetovanillone	COC1=CC(=CC=C1O)C(C)=O	1407.1	Standard non polar	33892256
Acetovanillone	COC1=CC(=CC=C1O)C(C)=O	1481.4	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 - Acetovanillone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-2900000000-c2b9fc9aff1c67a83c67	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetovanillone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetovanillone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Acetovanillone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-4900000000-17a85dc123d088c3aa49	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 10V, Positive-QTOF	splash10-014i-0900000000-498ed957aa15729fb0a4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 20V, Positive-QTOF	splash10-014i-0900000000-c1c53a9c0ce83907c31f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 40V, Positive-QTOF	splash10-0f6t-4900000000-9523f4aee91ded7398fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 10V, Negative-QTOF	splash10-014i-0900000000-dd966d68c334c4588c5a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 20V, Negative-QTOF	splash10-014i-0900000000-f50acbb85458094718fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 40V, Negative-QTOF	splash10-05mn-5900000000-38c38f7aec7f03fc4aa6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 10V, Negative-QTOF	splash10-014i-0900000000-5dea0e2df5cd18252bf0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 20V, Negative-QTOF	splash10-066s-0900000000-4aa899ac7457495c236b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 40V, Negative-QTOF	splash10-0006-9200000000-488dceb176525121ae13	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 10V, Positive-QTOF	splash10-0006-9300000000-a7b7fde927bc2ff25c6e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 20V, Positive-QTOF	splash10-0006-9100000000-fa257fa9b73b26e921ad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetovanillone 40V, Positive-QTOF	splash10-002f-9000000000-9160fcb70adace18630c	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

DB12618

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

Apocynin

METLIN ID

Not Available

PubChem Compound

2214

PDB ID

Not Available

ChEBI ID

2781

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1057511

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 Acetovanillone (HMDB0247918)

MOL for HMDB0247918 (Acetovanillone)

3D MOL for HMDB0247918 (Acetovanillone)

3D SDF for HMDB0247918 (Acetovanillone)

3D-SDF for HMDB0247918 (Acetovanillone)

PDB for HMDB0247918 (Acetovanillone)

3D PDB for HMDB0247918 (Acetovanillone)

SMILES for HMDB0247918 (Acetovanillone)

INCHI for HMDB0247918 (Acetovanillone)

Structure for HMDB0247918 (Acetovanillone)

3D Structure for HMDB0247918 (Acetovanillone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra