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Showing metabocard for Eugenol (HMDB0005809)

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enzymes (4) Show 4 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-23 13:27:56 UTC
Update Date2023-02-21 17:17:08 UTC
HMDB IDHMDB0005809
Secondary Accession Numbers
  • HMDB05809
Metabolite Identification
Common NameEugenol
DescriptionEugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from guaiacol, with an allyl chain positioned para to the hydroxy group. It is soluble in water, alcohol, chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol is widely distributed in plants. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID:15089054  ; PMID:935250  ) and acts as positive allosteric modulators of the GABA-A receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID:27771920  ).
Structure
Data?1676999828
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005809 (Eugenol)


  Mrv1652309272007442D          

 12 12  0  0  0  0            999 V2000
    0.5806    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1337    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1337    0.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    0.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    0.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    1.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626    1.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    0.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0096    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0005809 (Eugenol)

HMDB0005809
     RDKit          3D
Eugenol
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.2944    1.5143    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8381    0.3394   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0193   -0.4542    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707   -0.7369    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4540   -1.8759   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134   -2.1670   -1.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -1.2801   -0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896   -1.5788   -1.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931   -0.1450   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416    0.7115    0.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523    1.8799    0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427    0.1574    0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1082    1.9600    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904    2.0957   -0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -0.0381   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5975   -1.4054    0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530    0.0813    1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2603   -2.5671   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -3.0651   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9082   -1.0305   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4735    2.2932    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9794    1.6176    1.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    2.6327    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    1.0609    0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
  2 15  1  0
  3 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 HMDB0005809 (Eugenol)


  Mrv1652309272007442D          

 12 12  0  0  0  0            999 V2000
    0.5806    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1337    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1337    0.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    0.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    0.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    1.9298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626    1.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    0.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0096    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005809

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

> <INCHI_KEY>
RRAFCDWBNXTKKO-UHFFFAOYSA-N

> <FORMULA>
C10H12O2

> <MOLECULAR_WEIGHT>
164.2011

> <EXACT_MASS>
164.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.896536620818402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
2.6105799616666663

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.941818320747016

> <JCHEM_PKA_STRONGEST_BASIC>
-4.892303223457161

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
48.7894

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eugenol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0005809 (Eugenol)

HMDB0005809
     RDKit          3D
Eugenol
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.2944    1.5143    0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8381    0.3394   -0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0193   -0.4542    0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707   -0.7369    0.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4540   -1.8759   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134   -2.1670   -1.1312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8370   -1.2801   -0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0896   -1.5788   -1.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931   -0.1450   -0.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6416    0.7115    0.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523    1.8799    0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427    0.1574    0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1082    1.9600    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904    2.0957   -0.5780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -0.0381   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5975   -1.4054    0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530    0.0813    1.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2603   -2.5671   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9878   -3.0651   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9082   -1.0305   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4735    2.2932    1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9794    1.6176    1.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8310    2.6327    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2060    1.0609    0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
  2 15  1  0
  3 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 HMDB0005809 (Eugenol)

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  C   UNK     0       1.084   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.292   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.084   0.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.418   1.292   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.418   2.832   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.583   3.602   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.917   2.832   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.583   0.522   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.751   3.602   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.085   2.832   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.419   3.602   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1   10                                                  
CONECT    7    2    8                                                       
CONECT    8    7                                                            
CONECT    9    3                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0005809 (Eugenol)

COMPND    HMDB0005809
HETATM    1  C1  UNL     1       3.294   1.514   0.099  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.838   0.339  -0.267  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.019  -0.454   0.669  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.671  -0.737   0.133  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.454  -1.876  -0.612  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.813  -2.167  -1.131  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.837  -1.280  -0.874  1.00  0.00           C  
HETATM    8  O1  UNL     1      -3.090  -1.579  -1.394  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.593  -0.145  -0.124  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.642   0.712   0.108  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.452   1.880   0.864  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.343   0.157   0.398  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.108   1.960   1.071  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.890   2.096  -0.578  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.070  -0.038  -1.262  1.00  0.00           H  
HETATM   16  H4  UNL     1       2.598  -1.405   0.845  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.953   0.081   1.639  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.260  -2.567  -0.810  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.988  -3.065  -1.720  1.00  0.00           H  
HETATM   20  H8  UNL     1      -3.908  -1.030  -1.285  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.473   2.293   1.086  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.979   1.618   1.823  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.831   2.633   0.342  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.206   1.061   0.979  1.00  0.00           H  
CONECT    1    2    2   13   14
CONECT    2    3   15
CONECT    3    4   16   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 HMDB0005809 (Eugenol)

COC1=CC(CC=C)=CC=C1O
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INCHI for HMDB0005809 (Eugenol)

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,3,4-EugenolChEBI
1-Allyl-3-methoxy-4-hydroxybenzeneChEBI
1-Allyl-4-hydroxy-3-methoxybenzeneChEBI
1-Hydroxy-2-methoxy-4-allylbenzeneChEBI
1-Hydroxy-2-methoxy-4-prop-2-enylbenzeneChEBI
1-Hydroxy-2-methoxy-4-propenylbenzeneChEBI
2-Hydroxy-5-allylanisoleChEBI
2-Methoxy-1-hydroxy-4-allylbenzeneChEBI
2-Methoxy-4-(2-propen-1-yl)phenolChEBI
2-Methoxy-4-(2-propenyl)phenolChEBI
2-Methoxy-4-allylphenolChEBI
2-Methoxy-4-prop-2-enyl-phenolChEBI
2-Methoxy-4-prop-2-enylphenolChEBI
4-Allyl-1-hydroxy-2-methoxybenzeneChEBI
4-Allyl-2-methoxyphenolChEBI
4-Allylcatechol-2-methyl etherChEBI
4-AllylguaiacolChEBI
4-Hydroxy-3-methoxy-1-allylbenzeneChEBI
AllylguaiacolChEBI
Caryophyllic acidChEBI
Eugenic acidChEBI
p-AllylguaiacolChEBI
p-EugenolChEBI
CaryophyllateGenerator
EugenateGenerator
2-Methoxy-4-(3-propenyl)phenolHMDB
2-Methoxy-4-(prop-2-en-1-yl)phenolHMDB
4-Allyl-2-methoxy-phenolHMDB
4-Allylcatechol 2-methyl etherHMDB
4-Hydroxy-3-methoxyallylbenzeneHMDB
5-AllylguaiacolHMDB
EngenolHMDB
Eugenol (natural)HMDB
Synthetic eugenolHMDB
2-Methoxy-4-(2'-propenyl)phenolPhytoBank
2-Methoxy-4-(2’-propenyl)phenolPhytoBank
2-Methoxy-4-[2-allyl]phenolPhytoBank
3-(3-Methoxy-4-hydroxyphenyl)propenePhytoBank
3-(4-Hydroxy-3-methoxyphenyl)-1-propenePhytoBank
4-AllenylguaiacolPhytoBank
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name2-methoxy-4-(prop-2-en-1-yl)phenol
Traditional Nameeugenol
CAS Registry Number97-53-0
SMILES
COC1=CC(CC=C)=CC=C1O
InChI Identifier
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
InChI KeyRRAFCDWBNXTKKO-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationEnvironmental roleBiological roleIndirect biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point-12.00 to -10.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point252.00 to 253.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility754 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.270The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP2.66ALOGPS
logP2.61ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)9.94ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.79 m³·mol⁻¹ChemAxon
Polarizability17.9 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.02231661259
DarkChem[M-H]-134.84831661259
DeepCCS[M+H]+136.28130932474
DeepCCS[M-H]-133.68930932474
DeepCCS[M-2H]-170.16230932474
DeepCCS[M+Na]+145.31930932474
AllCCS[M+H]+134.432859911
AllCCS[M+H-H2O]+129.932859911
AllCCS[M+NH4]+138.632859911
AllCCS[M+Na]+139.832859911
AllCCS[M-H]-133.832859911
AllCCS[M+Na-2H]-134.932859911
AllCCS[M+HCOO]-136.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.4.79 minutes32390414
Predicted by Siyang on May 30, 202213.0947 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.78 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1823.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid397.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid162.5 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid251.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid218.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid557.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid550.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)103.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1219.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid438.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1171.8 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid363.0 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid429.1 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate412.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA316.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water27.8 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EugenolCOC1=CC(CC=C)=CC=C1O2182.2Standard polar33892256
EugenolCOC1=CC(CC=C)=CC=C1O1341.4Standard non polar33892256
EugenolCOC1=CC(CC=C)=CC=C1O1367.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Eugenol,1TMS,isomer #1C=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C11434.2Semi standard non polar33892256
Eugenol,1TBDMS,isomer #1C=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C11688.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-0ik9-5900000000-3d3a9e4f2500747410032017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-03di-2900000000-395df8510f0db4933abe2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-03di-6900000000-1afdd3b83f6832b11f702017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-03di-4900000000-1d96ae8b031e47e131122017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-0ik9-6900000000-def0c646d72c040b58da2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-03di-0900000000-dfa64951eb648f5c9df12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-0ik9-5900000000-3d3a9e4f2500747410032018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-03di-2900000000-395df8510f0db4933abe2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-03di-6900000000-1afdd3b83f6832b11f702018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-03di-4900000000-1d96ae8b031e47e131122018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-0ik9-6900000000-def0c646d72c040b58da2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Eugenol EI-B (Non-derivatized)splash10-03di-0900000000-dfa64951eb648f5c9df12018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eugenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ms-1900000000-da27a86009649c1553182016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eugenol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-8790000000-0d0c6f0e58d7dc3e56202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eugenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Eugenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0il0-6900000000-ff0dc492bab70317bb2a2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOFsplash10-014i-0900000000-4541582e8f6395e2fa872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-84f950d2fc0742e324d52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOFsplash10-0ab9-0900000000-4c037643a10913a70f5e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0900000000-83f8f32dfd9b94fb1d242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol LC-ESI-QTOF , positive-QTOFsplash10-0a4i-2900000000-c65a2dab49b8ebb431da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol Linear Ion Trap , positive-QTOFsplash10-001i-0900000000-65a67ccd1df0d2f1796f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol 40V, Positive-QTOFsplash10-0a4i-0900000000-83f8f32dfd9b94fb1d242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol 30V, Positive-QTOFsplash10-0ab9-0900000000-4c037643a10913a70f5e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol 10V, Positive-QTOFsplash10-014i-0900000000-4541582e8f6395e2fa872021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol 20V, Positive-QTOFsplash10-00di-0900000000-84f950d2fc0742e324d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol 10V, Positive-QTOFsplash10-014i-0900000000-f5092971e88a27de65e92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol 50V, Positive-QTOFsplash10-0a4i-2900000000-c65a2dab49b8ebb431da2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Eugenol 40V, Positive-QTOFsplash10-0a4i-0900000000-7beab8e102e0252d1a872021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 10V, Positive-QTOFsplash10-014i-0900000000-9d2a857e8a482a0611272015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 20V, Positive-QTOFsplash10-014i-2900000000-9c846765367542bf4db12015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 40V, Positive-QTOFsplash10-0fr6-9500000000-98fcaf3ccca850c34bd32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 10V, Negative-QTOFsplash10-03di-0900000000-835320dc79855273af7f2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 20V, Negative-QTOFsplash10-03di-0900000000-3a70eb9601589d9108a12015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 40V, Negative-QTOFsplash10-052e-4900000000-1c4834945c53d64bab3b2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 10V, Negative-QTOFsplash10-03di-0900000000-8db47caa9667c101bd0f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 20V, Negative-QTOFsplash10-03ka-0900000000-ab5855c31f23e61c7f542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 40V, Negative-QTOFsplash10-03k9-3900000000-868b72d9162a6b3078292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 10V, Positive-QTOFsplash10-0159-0900000000-63a94aabae02f360ee772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 20V, Positive-QTOFsplash10-05nr-1900000000-ce4d363c5e701cb34dfd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Eugenol 40V, Positive-QTOFsplash10-004i-9000000000-8e444a7d43baeb4d68f02021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.5 +/- 0.03 uMAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09086
Phenol Explorer Compound ID646
FooDB IDFDB012171
KNApSAcK IDC00000619
Chemspider ID13876103
KEGG Compound IDC10453
BioCyc IDCPD-6481
BiGG IDNot Available
Wikipedia LinkEugenol
METLIN ID4022
PubChem Compound3314
PDB IDEOL
ChEBI ID4917
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004991
References
Synthesis ReferenceOgiso, Akira; Kobayashi, Shinsaku. a-Vinylbenzylalcohol derivatives. Jpn. Kokai Tokkyo Koho (1974), 6 pp. CODEN: JKXXAF JP 49036644 19740405 Showa. CAN 82:16534 AN 1975:16534
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Jadhav BK, Khandelwal KR, Ketkar AR, Pisal SS: Formulation and evaluation of mucoadhesive tablets containing eugenol for the treatment of periodontal diseases. Drug Dev Ind Pharm. 2004 Feb;30(2):195-203. doi: 10.1081/ddc-120028715. [PubMed:15089054 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 2B28
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Enzyme Details
2. 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
Eugenol → 3,4,5-trihydroxy-6-[2-methoxy-4-(prop-2-en-1-yl)phenoxy]oxane-2-carboxylic aciddetails
Enzyme Details
3. UDP-glucuronosyltransferase 2B17
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. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:
UGT2B17
Uniprot ID:
O75795
Molecular weight:
61094.915
Enzyme Details
4. 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
Eugenol → [2-methoxy-4-(prop-2-en-1-yl)phenyl]oxidanesulfonic aciddetails