MiMeDB: Showing metabocard for 4-Allyl-2,6-dimethyoxphenol (MMDBc0033580)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:54:25 UTC

Update Date

2024-09-29 11:34:13 UTC

Metabolite ID

MMDBc0033580

Metabolite Identification

Common Name

4-Allyl-2,6-dimethyoxphenol

Description

Methoxyeugenol, also known as 4-allylsyringol, 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. Methoxyeugenol is a sweet, bacon, and burnt tasting compound. Methoxyeugenol has been detected, but not quantified, in herbs and spices. This could make methoxyeugenol a potential biomarker for the consumption of these foods.

Structure

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


  Mrv1652305271900202D          

 14 14  0  0  0  0            999 V2000
   15.1821  -14.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1823  -13.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8980  -15.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4678  -15.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8997  -13.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4665  -13.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6123  -14.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9024  -15.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6139  -13.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7522  -13.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1851  -16.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3252  -13.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0376  -13.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7503  -13.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033580

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=CC(CC=C)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3

> <INCHI_KEY>
FWMPKHMKIJDEMJ-UHFFFAOYSA-N

> <FORMULA>
C11H14O3

> <MOLECULAR_WEIGHT>
194.2271

> <EXACT_MASS>
194.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.53726426167309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.4529086959999997

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.335852773119273

> <JCHEM_PKA_STRONGEST_BASIC>
-4.603104312142213

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
55.25260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      28.340 -27.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.340 -25.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.676 -28.242   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.007 -28.234   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      29.679 -25.153   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      27.004 -25.148   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      31.010 -27.473   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      29.684 -29.785   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      31.013 -25.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.671 -25.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.346 -30.556   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.340 -25.159   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.670 -25.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.001 -25.150   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1                                                            
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3    9                                                       
CONECT    8    3   11                                                       
CONECT    9    5   12    7                                                  
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0041194
HETATM    1  C1  UNL     1       2.758  -0.343  -1.298  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.122  -0.510  -0.044  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.148  -0.449   1.059  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.774  -0.192   0.617  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.291   1.091   0.503  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.001   1.359   0.088  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.467   2.675  -0.020  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.643   3.771   0.288  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.813   0.280  -0.215  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.094   0.518  -0.627  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.351  -1.037  -0.109  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.222  -2.037  -0.428  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.973  -3.403  -0.393  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.058  -1.248   0.308  1.00  0.00           C  
HETATM   15  H1  UNL     1       1.713  -0.156  -1.526  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.429  -0.377  -2.140  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.161  -0.694   0.171  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.158  -1.462   1.554  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.462   0.337   1.802  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.965   1.896   0.751  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.271   4.679   0.405  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.146   3.624   1.281  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.129   3.950  -0.490  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.445   1.455  -0.710  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.922  -3.697  -0.492  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.454  -3.834   0.529  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.514  -3.913  -1.242  1.00  0.00           H  
HETATM   28  H14 UNL     1       0.264  -2.284   0.378  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5    5   14
CONECT    5    6   20
CONECT    6    7    9    9
CONECT    7    8
CONECT    8   21   22   23
CONECT    9   10   11
CONECT   10   24
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   25   26   27
CONECT   14   28
END

Synonyms

Value	Source
2,6-Dimethoxy-4-(2-propenyl)-phenol	HMDB
2,6-Dimethoxy-4-(2-propenyl)phenol, 9ci	HMDB
2,6-Dimethoxy-4-allylphenol	HMDB, MeSH
2,6-Dimethoxychavicol	HMDB
4-(2-Propenyl)-2,6-dimethoxyphenol	HMDB
4-Allyl-2,6-dimethoxy-phenol	HMDB
4-Allyl-2,6-dimethoxyphenol	HMDB
4-Allyl-2,6-dimethoxyphenol, 8ci	HMDB
4-Allyl-2,6-dimetoxyphenol	HMDB
4-Allylsyringol	HMDB, MeSH
4-Hydroxy-3,5-dimethoxyallylbenzene	HMDB, MeSH
N-Allylcyclohexylamine	HMDB
Phenol, 2,6-dimethoxy-4-(2-propenyl)- (9ci)	HMDB
Phenol, 4-(2-propenyl)-2,6-dimethoxy	HMDB
Phenol, 4-allyl-2,6-dimethoxy- (8ci)	HMDB
2,6-Dimethoxy-4-(2-propenyl)phenol	MeSH
6-Methoxyeugenol	MeSH

Molecular Formula

C₁₁H₁₄O₃

Average Mass

194.2271

Monoisotopic Mass

194.094294314

IUPAC Name

2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

Traditional Name

2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

CAS Registry Number

6627-88-9

SMILES

COC1=CC(CC=C)=CC(OC)=C1O

InChI Identifier

InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3

InChI Key

FWMPKHMKIJDEMJ-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

M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:86562 )
phenylpropanoid (CHEBI:86562 )
dimethoxybenzene (CHEBI:86562 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.59 g/L	ALOGPS
logP	2.23	ALOGPS
logP	2.45	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.25 m³·mol⁻¹	ChemAxon
Polarizability	20.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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	splash10-0fvl-1900000000-6bb088a84e5d530fd6a9	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0umi-6290000000-ddd8fa9b2271b5e885fa	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	splash10-0002-0900000000-bf95219cde86264ddd0e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1900000000-b3789d49cb1d02ff5e01	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-7900000000-2b4993fb9c656f50c42f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-1cb6aa76e853c97dffa4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-7a91ae9052ae5aad302c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6s-3900000000-2d0b6fcc14c0098a2b40	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-62e0a52145f670b429c1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1900000000-9d68b2e71ed843fa1b9a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ou-9100000000-2bed599e076c0fa0e319	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-b336d2e98c182ff7e0b0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-1900000000-fb6a83b5e663fc04cc80	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02t9-9300000000-a8dc328f94fd3fc6319f	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100.40 MHz, CDCl₃, experimental)		2016-09-19	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

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

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		Illicium verum	FooDB	31437929
Plant		Musa acuminata	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0041194

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021092

KNApSAcK ID

C00055253

Chemspider ID

196968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

226486

PDB ID

Not Available

ChEBI ID

86562

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Loscos N, Hernandez-Orte P, Cacho J, Ferreira V: Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions. J Agric Food Chem. 2007 Aug 8;55(16):6674-84. doi: 10.1021/jf0702343. Epub 2007 Jul 7. [PubMed:17616208 ]
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 4-Allyl-2,6-dimethyoxphenol (MMDBc0033580)

MOL for #<Metabolite:0x00007f46d026a368>

3D MOL for #<Metabolite:0x00007f46d026a368>

3D SDF for #<Metabolite:0x00007f46d026a368>

3D-SDF for #<Metabolite:0x00007f46d026a368>

PDB for #<Metabolite:0x00007f46d026a368>

3D PDB for #<Metabolite:0x00007f46d026a368>

SMILES for #<Metabolite:0x00007f46d026a368>

INCHI for #<Metabolite:0x00007f46d026a368>

Structure for #<Metabolite:0x00007f46d026a368>

3D Structure for #<Metabolite:0x00007f46d026a368>