Showing metabocard for 4-Allyl-2-methoxyphenol (MMDBc0033579)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:54:23 UTC
Update Date2024-04-30 20:13:02 UTC
Metabolite IDMMDBc0033579
Metabolite Identification
Common Name4-Allyl-2-methoxyphenol
Description4-Allyl-2-methoxyphenol, also known as eugenol, 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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005634c1c00e80>


  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 #<Metabolite:0x00005634c1c00e80>

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 #<Metabolite:0x00005634c1c00e80>


  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>
MMDBc0033579

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00005634c1c00e80>

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
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PDB for #<Metabolite:0x00005634c1c00e80>

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 #<Metabolite:0x00005634c1c00e80>

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 #<Metabolite:0x00005634c1c00e80>

COC1=CC(CC=C)=CC=C1O
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INCHI for #<Metabolite:0x00005634c1c00e80>

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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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
Molecular FormulaC10H12O2
Average Mass164.2011
Monoisotopic Mass164.083729628
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