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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:39 UTC

Update Date

2023-02-21 17:22:25 UTC

HMDB ID

HMDB0032590

Secondary Accession Numbers

HMDB32590

Metabolite Identification

Common Name

Zingerone

Description

Zingerone, also known as vanillylacetone or [0]-paradol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Zingerone is a sweet, animal, and clove tasting compound. Zingerone is found, on average, in the highest concentration within pot marjorams (Origanum onites) and gingers (Zingiber officinale). Zingerone has also been detected, but not quantified in, fruits and herbs and spices. This could make zingerone a potential biomarker for the consumption of these foods. Zingerone 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 significant number of articles have been published on Zingerone.

Structure

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


  Mrv0541 05061306352D          

 14 14  0  0  0  0            999 V2000
    2.1434   -2.8875    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    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  3  1  0  0  0  0
  6  5  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032590

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(CCC(C)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3

> <INCHI_KEY>
OJYLAHXKWMRDGS-UHFFFAOYSA-N

> <FORMULA>
C11H14O3

> <MOLECULAR_WEIGHT>
194.2271

> <EXACT_MASS>
194.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.94858198532754

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(4-hydroxy-3-methoxyphenyl)butan-2-one

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.9239517056666666

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.59152516614606

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.945876444592866

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8903376293669645

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
53.96180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zingerone

> <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       4.001  -5.390   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       2.667  -3.080   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   14                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    9   11                                                       
CONECT    8    1    3   12                                                  
CONECT    9    4    5    7                                                  
CONECT   10    6   11   13                                                  
CONECT   11    7   10   14                                                  
CONECT   12    8                                                            
CONECT   13   10                                                            
CONECT   14    2   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0032590
HETATM    1  C1  UNL     1      -3.820  -1.878   1.327  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.239  -1.013   0.613  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.304  -0.206   0.108  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.981  -0.186   0.579  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.027   0.644   0.062  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.371   0.629   0.543  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.234  -0.309  -0.277  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.638  -0.313   0.226  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.479   0.917  -0.047  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.164  -1.215   0.838  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.353   1.512  -0.968  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.639   1.521  -1.456  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.592   0.670  -0.918  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.909   0.673  -1.412  1.00  0.00           O  
HETATM   15  H1  UNL     1      -4.371  -2.701   0.763  1.00  0.00           H  
HETATM   16  H2  UNL     1      -4.596  -1.445   2.053  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.097  -2.460   2.004  1.00  0.00           H  
HETATM   18  H4  UNL     1      -0.768  -0.883   1.385  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.410   0.237   1.581  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.789   1.652   0.567  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.245  -0.054  -1.341  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.811  -1.349  -0.143  1.00  0.00           H  
HETATM   23  H9  UNL     1       4.114   1.444  -0.940  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.510   1.539   0.874  1.00  0.00           H  
HETATM   25  H11 UNL     1       5.520   0.588  -0.235  1.00  0.00           H  
HETATM   26  H12 UNL     1       0.418   2.148  -1.351  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.890   2.206  -2.264  1.00  0.00           H  
HETATM   28  H14 UNL     1      -4.118   1.313  -2.171  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   18
CONECT    5    6   11   11
CONECT    6    7   19   20
CONECT    7    8   21   22
CONECT    8    9   10   10
CONECT    9   23   24   25
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14
CONECT   14   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(0)-Paradol	ChEBI
(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone	ChEBI
2-(4-Hydroxy-3-methoxyphenyl)ethyl methyl ketone	ChEBI
3-Methoxy-4-hydroxybenzylacetone	ChEBI
4-(3-Methoxy-4-hydroxyphenyl)-2-butanone	ChEBI
4-(3-Methoxy-4-hydroxyphenyl)butan-2-one	ChEBI
4-(4-Hydroxy-3-methoxyphenyl)-2-butanone	ChEBI
4-Hydroxy-3-methoxybenzylacetone	ChEBI
[0]-Paradol	ChEBI
Gingerone	ChEBI
Vanillylacetone	ChEBI
Zingherone	ChEBI
Zingiberone	ChEBI
0 Paradol	MeSH
4-(4-Hydroxy-3-methoxyphenyl)butan-2-one	MeSH
Vanillyl acetone	MeSH
4-(4-Hydroxy-3-methoxy-phenyl)-butan-2-one	HMDB
4-(4-Hydroxy-3-methoxyphenyl)-2-butanone, 9ci, 8ci	HMDB
FEMA 3124	HMDB
[0]Paradol	HMDB

Chemical Formula

C₁₁H₁₄O₃

Average Molecular Weight

194.2271

Monoisotopic Molecular Weight

194.094294314

IUPAC Name

4-(4-hydroxy-3-methoxyphenyl)butan-2-one

Traditional Name

zingerone

CAS Registry Number

122-48-5

SMILES

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

InChI Identifier

InChI=1S/C11H14O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h5-7,13H,3-4H2,1-2H3

InChI Key

OJYLAHXKWMRDGS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ketone
Ether
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:68657 )
monomethoxybenzene (CHEBI:68657 )
ketone (CHEBI:68657 )
Zingiber derived compounds (C17497 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032590)
Cytoplasm (HMDB: HMDB0032590)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032590)

Source

Exogenous

Exogenous (HMDB: HMDB0032590)

Food

Food (HMDB: HMDB0032590)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Herb

Pot marjoram (FooDB: FOOD00123)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Endogenous (HMDB: HMDB0032590)

Plant

Plant (HMDB: HMDB0032590)

Process

Not Available

Role

Industrial applicationBiological role

Adrenergic agent (HMDB: HMDB0032590)
Anti atherosclerotic (HMDB: HMDB0032590)
Anti-inflammatory (HMDB: HMDB0032590)
Anti mutagenic (HMDB: HMDB0032590)
Anti ulcer (HMDB: HMDB0032590)
Cardiotonic (HMDB: HMDB0032590)
Hypotensive (HMDB: HMDB0032590)
Paralytic (HMDB: HMDB0032590)
Secretogogue (HMDB: HMDB0032590)

Modulator

Inhibitor

EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (HMDB: HMDB0032590)

Enzyme inhibitor

5-lipoxygenase inhibitor (HMDB: HMDB0032590)
Cyclooxygenase inhibitor (HMDB: HMDB0032590)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	41 °C	Not Available
Boiling Point	141.00 to 0.50 °C. @ 0.00 mm Hg	The Good Scents Company Information System
Water Solubility	3571 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.168 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.57 g/L	ALOGPS
logP	2.02	ALOGPS
logP	1.92	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.95	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	4	ChemAxon
Refractivity	53.96 m³·mol⁻¹	ChemAxon
Polarizability	20.95 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
DarkChem	[M+H]+	145.958	31661259
DarkChem	[M-H]-	144.798	31661259
DeepCCS	[M+H]+	146.353	30932474
DeepCCS	[M-H]-	143.455	30932474
DeepCCS	[M-2H]-	179.92	30932474
DeepCCS	[M+Na]+	155.458	30932474
AllCCS	[M+H]+	143.3	32859911
AllCCS	[M+H-H2O]+	139.2	32859911
AllCCS	[M+NH4]+	147.2	32859911
AllCCS	[M+Na]+	148.3	32859911
AllCCS	[M-H]-	144.9	32859911
AllCCS	[M+Na-2H]-	145.7	32859911
AllCCS	[M+HCOO]-	146.7	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.	4.8 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2164 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.7 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1773.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	322.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	120.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	490.3 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	431.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1042.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	391.9 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	1086.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	353.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	268.1 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	26.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zingerone	COC1=C(O)C=CC(CCC(C)=O)=C1	2838.4	Standard polar	33892256
Zingerone	COC1=C(O)C=CC(CCC(C)=O)=C1	1599.4	Standard non polar	33892256
Zingerone	COC1=C(O)C=CC(CCC(C)=O)=C1	1641.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zingerone,1TMS,isomer #1	COC1=CC(CCC(C)=O)=CC=C1O[Si](C)(C)C	1769.5	Semi standard non polar	33892256
Zingerone,1TMS,isomer #2	COC1=CC(CC=C(C)O[Si](C)(C)C)=CC=C1O	1865.0	Semi standard non polar	33892256
Zingerone,1TMS,isomer #3	C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C	1809.7	Semi standard non polar	33892256
Zingerone,2TMS,isomer #1	COC1=CC(CC=C(C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1915.7	Semi standard non polar	33892256
Zingerone,2TMS,isomer #1	COC1=CC(CC=C(C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1870.9	Standard non polar	33892256
Zingerone,2TMS,isomer #2	C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	1837.0	Semi standard non polar	33892256
Zingerone,2TMS,isomer #2	C=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C	1829.9	Standard non polar	33892256
Zingerone,1TBDMS,isomer #1	COC1=CC(CCC(C)=O)=CC=C1O[Si](C)(C)C(C)(C)C	2009.5	Semi standard non polar	33892256
Zingerone,1TBDMS,isomer #2	COC1=CC(CC=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1O	2116.3	Semi standard non polar	33892256
Zingerone,1TBDMS,isomer #3	C=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2044.6	Semi standard non polar	33892256
Zingerone,2TBDMS,isomer #1	COC1=CC(CC=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2412.3	Semi standard non polar	33892256
Zingerone,2TBDMS,isomer #1	COC1=CC(CC=C(C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2358.9	Standard non polar	33892256
Zingerone,2TBDMS,isomer #2	C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2300.6	Semi standard non polar	33892256
Zingerone,2TBDMS,isomer #2	C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C	2291.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zingerone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5900000000-42ac2a1b364f92df5152	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zingerone GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9370000000-988fce303c33c65d61c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zingerone 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 - Zingerone 10V, Positive-QTOF	splash10-002b-0900000000-4c68e7e311ed162223a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 20V, Positive-QTOF	splash10-004s-1900000000-e0ac7417df02644e0761	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 40V, Positive-QTOF	splash10-0f9l-7900000000-2f6d6b18947145fb0dbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 10V, Negative-QTOF	splash10-0006-0900000000-8f3da5e61712d1ffacb3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 20V, Negative-QTOF	splash10-0006-2900000000-53b85d6dc1005c5d4df0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 40V, Negative-QTOF	splash10-0a4i-5900000000-f12fadc90e8da514347f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 10V, Negative-QTOF	splash10-0a4l-9700000000-885efff123d09c229869	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 20V, Negative-QTOF	splash10-0a4i-9500000000-6b1a5bf42da790be18f4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 40V, Negative-QTOF	splash10-059m-7900000000-fe627d4904dd2c51d333	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 10V, Positive-QTOF	splash10-000i-0900000000-5d0af36deea574d177be	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 20V, Positive-QTOF	splash10-0a4s-0900000000-f505f559b715ddb1b325	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zingerone 40V, Positive-QTOF	splash10-0a4i-6900000000-251b2e68bd1f83dfb714	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zingerone

METLIN ID

Not Available

PubChem Compound

31211

PDB ID

Not Available

ChEBI ID

68657

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1006231

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Morimoto Y, Shibata Y: Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice. Yakugaku Zasshi. 2010 Jul;130(7):983-7. [PubMed:20606379 ]
Kabuto H, Nishizawa M, Tada M, Higashio C, Shishibori T, Kohno M: Zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butanone] prevents 6-hydroxydopamine-induced dopamine depression in mouse striatum and increases superoxide scavenging activity in serum. Neurochem Res. 2005 Mar;30(3):325-32. [PubMed:16018576 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Zingerone → 3,4,5-trihydroxy-6-[2-methoxy-4-(3-oxobutyl)phenoxy]oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Zingerone → [2-methoxy-4-(3-oxobutyl)phenyl]oxidanesulfonic acid	details

Showing metabocard for Zingerone (HMDB0032590)

MOL for HMDB0032590 (Zingerone)

3D MOL for HMDB0032590 (Zingerone)

3D SDF for HMDB0032590 (Zingerone)

3D-SDF for HMDB0032590 (Zingerone)

PDB for HMDB0032590 (Zingerone)

3D PDB for HMDB0032590 (Zingerone)

SMILES for HMDB0032590 (Zingerone)

INCHI for HMDB0032590 (Zingerone)

Structure for HMDB0032590 (Zingerone)

3D Structure for HMDB0032590 (Zingerone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions

Reactions