Showing metabocard for E-4-Propenyl-2-methoxyphenol (MMDBc0033627)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:56:30 UTC
Update Date2024-04-30 20:13:56 UTC
Metabolite IDMMDBc0033627
Metabolite Identification
Common NameE-4-Propenyl-2-methoxyphenol
DescriptionIsoeugenol, also known as E-4-propenyl-2-methoxyphenol, is an isomer of eugenol, wherein the double bond on the alkyl chain is shifted by one carbon. It also known as propenylgualacol, 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. Isoeugenol is also classified as a phenylpropene, a propenyl-substituted guaiacol. Isoeugenol may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a pale, yellow liquid. Isoeugenol is very slightly soluble in water and soluble in organic solvents. It has a spicy, sweet, carnation-like odour and tastes of sweet spice and clove. Isoeugenol is a widely used food flavoring agent and a perfuming agent. As a food flavoring agent, it is responsible for the flavor of nutmeg (in pumpkin pies), As a fragrance, it is extensively used as a scent agent in consumer products such as soaps, shampoos, perfumes, detergents and bath tissues (often labeled as ‚ÄúFragrance‚Äù rather than isoeugenol). However, some individuals can develop allergies to isoeugenol as it appears to be a strong contact allergen (PMID:10554062  ). Isoeugenol can be prepared from eugenol by heating. In addition to its industrial production via eugenol, isoeugenol can also be extracted from certain essential oils especially from clove oil and cinnamon. It is found naturally in a wide number of foods, spices and plants including allspice, basil, blueberries, cinnamon, cloves, coffee, dill, ginber, nutmeg, thyme and turmeric. Isoeugenol is also a component of wood smoke and liquid smoke. It is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses. Isoeugenol (specifically the acetate ester) has also been used in the production of vanillin. Isoeugenol is one of several non-cannabinoid phenols found in cannabis plants (PMID:6991645  ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fecae1dea78>


  Mrv1652309042000312D          

 12 12  0  0  0  0            999 V2000
 9999.652410000.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.366710000.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.793310000.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.222110000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.507710000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5077 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2221 9998.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9366 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.936610000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.081310000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.078610000.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7932 9998.9783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1  9  1  0  0  0  0
  5  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  6 12  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fecae1dea78>

HMDB0005802
     RDKit          3D
Isoeugenol
 24 24  0  0  0  0  0  0  0  0999 V2000
   -4.0998   -0.7656    0.9030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -0.1940    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988   -0.4208    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008    0.0856   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217    0.8724   -1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.3373   -1.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    1.0225   -1.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0415    1.4654   -1.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    0.2313   -0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579   -0.0928    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -0.8951    1.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -0.2272    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1819   -1.8180    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -0.7233    1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268   -0.2522    0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    0.4151   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768   -1.0432    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4731    1.1394   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5962    1.9620   -2.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    2.0410   -2.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5998   -1.7604    1.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522   -1.2631    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0578   -0.2722    2.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -0.8439    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
 11 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fecae1dea78>


  Mrv1652309042000312D          

 12 12  0  0  0  0            999 V2000
 9999.652410000.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.366710000.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.793310000.6288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.222110000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.507710000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5077 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2221 9998.9783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9366 9999.3908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.936610000.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.081310000.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.078610000.2166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7932 9998.9783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9  4  1  0  0  0  0
  1  9  1  0  0  0  0
  5  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  6 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033627

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+

> <INCHI_KEY>
BJIOGJUNALELMI-ONEGZZNKSA-N

> <FORMULA>
C10H12O2

> <MOLECULAR_WEIGHT>
164.2011

> <EXACT_MASS>
164.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.29788150152988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.6353462913333328

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.013922795139589

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8937792336789006

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
49.8619

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoeugenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007fecae1dea78>

HMDB0005802
     RDKit          3D
Isoeugenol
 24 24  0  0  0  0  0  0  0  0999 V2000
   -4.0998   -0.7656    0.9030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9305   -0.1940    0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6988   -0.4208    0.5179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5008    0.0856   -0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217    0.8724   -1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.3373   -1.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    1.0225   -1.3833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0415    1.4654   -1.9630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129    0.2313   -0.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579   -0.0928    0.2665 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -0.8951    1.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7611   -0.2272    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1819   -1.8180    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9271   -0.7233    1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268   -0.2522    0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    0.4151   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5768   -1.0432    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4731    1.1394   -1.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5962    1.9620   -2.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    2.0410   -2.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5998   -1.7604    1.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3522   -1.2631    1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0578   -0.2722    2.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -0.8439    1.2330 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  5 18  1  0
  6 19  1  0
  8 20  1  0
 11 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

PDB for #<Metabolite:0x00007fecae1dea78>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.0188667.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3518667.070   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8660.6818667.840   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8663.3488667.840   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.0148667.070   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.0148665.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.3488664.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.6828665.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.6828667.070   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.6858667.840   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.3478667.071   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8660.6818664.759   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   10                                                       
CONECT    3    5   11                                                       
CONECT    4    5    9                                                       
CONECT    5    4    6    3                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4    1                                                  
CONECT   10    2                                                            
CONECT   11    3                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for #<Metabolite:0x00007fecae1dea78>

COMPND    HMDB0005802
HETATM    1  C1  UNL     1      -4.100  -0.766   0.903  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.931  -0.194   0.139  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.699  -0.421   0.518  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.501   0.086  -0.151  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.522   0.872  -1.276  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.620   1.337  -1.888  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.865   1.023  -1.383  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.041   1.465  -1.963  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.913   0.231  -0.252  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.158  -0.093   0.267  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.323  -0.895   1.419  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.761  -0.227   0.351  1.00  0.00           C  
HETATM   13  H1  UNL     1      -4.182  -1.818   0.569  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.927  -0.723   1.982  1.00  0.00           H  
HETATM   15  H3  UNL     1      -5.027  -0.252   0.578  1.00  0.00           H  
HETATM   16  H4  UNL     1      -3.095   0.415  -0.738  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.577  -1.043   1.412  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.473   1.139  -1.699  1.00  0.00           H  
HETATM   19  H7  UNL     1       0.596   1.962  -2.781  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.960   2.041  -2.788  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.600  -1.760   1.362  1.00  0.00           H  
HETATM   22  H10 UNL     1       4.352  -1.263   1.523  1.00  0.00           H  
HETATM   23  H11 UNL     1       3.058  -0.272   2.301  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.784  -0.844   1.233  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   16
CONECT    3    4   17
CONECT    4    5    5   12
CONECT    5    6   18
CONECT    6    7    7   19
CONECT    7    8    9
CONECT    8   20
CONECT    9   10   12   12
CONECT   10   11
CONECT   11   21   22   23
CONECT   12   24
END
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SMILES for #<Metabolite:0x00007fecae1dea78>

COC1=CC(\C=C\C)=CC=C1O
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INCHI for #<Metabolite:0x00007fecae1dea78>

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
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Synonyms
ValueSource
(e)-2-Methoxy-4-(prop-1-enyl)phenolChEBI
2-Methoxy-4-[(1E)-1-propenyl]phenolChEBI
2-Methoxy-4-propenylphenolChEBI
3-Methoxy-4-hydroxy-1-propen-1-ylbenzeneChEBI
3-Methoxy-4-hydroxypropenylbenzeneChEBI
4-Hydroxy-3-methoxy-1-propenylbenzeneChEBI
Iso-eugenol 2ChEBI
Isoeugenol (I)ChEBI
Isoeugenol eChEBI
Isoeugenol trans-formChEBI
PropenylgualacolChEBI
trans-2-Methoxy-4-(1-propenyl)phenolChEBI
trans-2-Methoxy-4-propenylphenolChEBI
trans-4-PropenylgualacolChEBI
trans-p-PropenylquaiacolChEBI
2-Methoxy-4-(prop-1-en-1-yl)phenolKegg
(e)-2-Methoxy-4- (1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-(1-propenyl)-phenolHMDB
(e)-2-Methoxy-4-propenyl-phenolHMDB
(E)-IsoeugenolHMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propaneHMDB
1-Hydroxy-2-methoxy-4-propen-1-ylbenzeneHMDB
2-Methoxy-4-(1-propenyl)-phenolHMDB
2-Methoxy-4-(1-propenyl)phenolHMDB
2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)HMDB
2-Methoxy-4-propenyl-phenolHMDB
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenolHMDB
4-Hydroxy-3-methoxy-1-propen-1-ylbenzeneHMDB
4-Hydroxy-3-methoxypropenylbenzeneHMDB
trans-IsoeugenolHMDB
Isoeugenol, (e)-isomerMeSH, HMDB
IsoeugenolMeSH
(E)-2-Methoxy-4-(1-propenyl)phenolHMDB
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenolHMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propeneHMDB
2-Methoxy-4(E)-1-propenylphenolHMDB
2-Methoxy-4-(1-propen-1-yl)phenolHMDB
2-Methoxy-4-(1E)-1-propen-1-ylphenolHMDB
2-Methoxy-4-[(E)-1-propenyl]phenolHMDB
3-Methoxy-4-hydroxy-1-propenylbenzeneHMDB
4-(1-Propenyl) GuaiacolHMDB
4-Hydroxy-3-methoxy-beta-methylstyreneHMDB
4-Hydroxy-3-methoxy-β-methylstyreneHMDB
4-PropenylguaiacolHMDB
iso-EugenolHMDB
trans-4-PropenylguaiacolHMDB
trans-p-PropenylguaiacolHMDB
Molecular FormulaC10H12O2
Average Mass164.2011
Monoisotopic Mass164.083729628
IUPAC Name2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol
Traditional Nameisoeugenol
CAS Registry Number5932-68-3
SMILES
COC1=CC(\C=C\C)=CC=C1O
InChI Identifier
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+
InChI KeyBJIOGJUNALELMI-ONEGZZNKSA-N