MiMeDB: Showing metabocard for Zingerone (MMDBc0033732)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:00:51 UTC

Update Date

2022-08-31 22:38:08 UTC

Metabolite ID

MMDBc0033732

Metabolite Identification

Common Name

Zingerone

Description

Zingerone is found in fruits. Reputed pungent principle of ginger (Zingiber officinale). Flavour material used in imitation fruit flavours, ginger beer, ginger ale etc. Also present in cranberry, raspberry and mang

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>
MMDBc0033732

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₁H₁₄O₃

Average Mass

194.2271

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5900000000-42ac2a1b364f92df5152	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9370000000-988fce303c33c65d61c8	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0900000000-4c68e7e311ed162223a5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004s-1900000000-e0ac7417df02644e0761	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f9l-7900000000-2f6d6b18947145fb0dbf	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-8f3da5e61712d1ffacb3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2900000000-53b85d6dc1005c5d4df0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-f12fadc90e8da514347f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4l-9700000000-885efff123d09c229869	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9500000000-6b1a5bf42da790be18f4	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-059m-7900000000-fe627d4904dd2c51d333	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-5d0af36deea574d177be	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-0900000000-f505f559b715ddb1b325	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-6900000000-251b2e68bd1f83dfb714	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0197061	Sulfotransferase 1A3	Enzyme	P0DMM9	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Essential oil	Zingiber officinale	FooDB	31437929
Plant	Rhizome	Zingiber officinale	FooDB	31437929
Plant	Shoot	Origanum onites	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0032590

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1007/s11064-005-2606-3. [PubMed:16018576 ]
Morimoto Y, Shibata Y: Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice. Yakugaku Zasshi. 2010 Jul;130(7):983-7. doi: 10.1248/yakushi.130.983. [PubMed:20606379 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Zingerone (MMDBc0033732)

MOL for #<Metabolite:0x00007f5a5661e5b0>

3D MOL for #<Metabolite:0x00007f5a5661e5b0>

3D SDF for #<Metabolite:0x00007f5a5661e5b0>

3D-SDF for #<Metabolite:0x00007f5a5661e5b0>

PDB for #<Metabolite:0x00007f5a5661e5b0>

3D PDB for #<Metabolite:0x00007f5a5661e5b0>

SMILES for #<Metabolite:0x00007f5a5661e5b0>

INCHI for #<Metabolite:0x00007f5a5661e5b0>

Structure for #<Metabolite:0x00007f5a5661e5b0>

3D Structure for #<Metabolite:0x00007f5a5661e5b0>