Showing metabocard for 4-Ethyl-2-methoxyphenol (MMDBc0033581)

Plant
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:54:27 UTC
Update Date2022-08-31 22:36:52 UTC
Metabolite IDMMDBc0033581
Metabolite Identification
Common Name4-Ethyl-2-methoxyphenol
Description4-Ethyl-2-methoxyphenol is a volatile phenol found in wines spoiled with the Brettanomyces wild yeast. It is produced by Brettanomyces as a result of enzymatic conversion of vinylphenols derived from cinnamic acids naturally present in the grape must. At low concentrations, this compound is thought to add to wine complexity, but at high concentrations the wine is considered spoiled and has been described as animal, barnyard, stable, phenolic, and mousy. [PMID: 17850808 , PMID: 17676867 ]
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000560be06822d8>


  Mrv0541 05061311402D          

 11 11  0  0  0  0            999 V2000
    1.4289   -1.6500    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
    0.7145   -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
    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    2.0625    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
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  2  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000560be06822d8>

HMDB0040175
     RDKit          3D
4-Ethyl-2-methoxyphenol
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.7950   -1.3032   -0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -0.0256   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    0.3411   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9768    1.1368    1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683    1.4839    1.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3997    1.0474    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856    1.3581    1.9531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531    0.2515    0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7001   -0.1974   -0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -1.0171   -1.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -0.0899   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789   -2.2005   -0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665   -1.2927   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873   -1.3192    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -0.0888   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092    0.7929   -0.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9525    1.4812    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403    2.1143    2.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5127    1.9453    2.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -0.3760   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -1.8646   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711   -1.4555   -1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685   -0.7219   -1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
M  END
Download

3D SDF for #<Metabolite:0x0000560be06822d8>


  Mrv0541 05061311402D          

 11 11  0  0  0  0            999 V2000
    1.4289   -1.6500    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
    0.7145   -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
    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    2.0625    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
  3  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  8  1  0  0  0  0
 11  2  1  0  0  0  0
 11  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033581

> <DATABASE_NAME>
MIME

> <SMILES>
CCC1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3

> <INCHI_KEY>
CHWNEIVBYREQRF-UHFFFAOYSA-N

> <FORMULA>
C9H12O2

> <MOLECULAR_WEIGHT>
152.1904

> <EXACT_MASS>
152.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
16.75074072546328

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-ethyl-2-methoxyphenol

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.469999283

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.30026611860602

> <JCHEM_PKA_STRONGEST_BASIC>
-4.891012437808494

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
44.14430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-ethylguaiacol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for #<Metabolite:0x0000560be06822d8>

HMDB0040175
     RDKit          3D
4-Ethyl-2-methoxyphenol
 23 23  0  0  0  0  0  0  0  0999 V2000
    2.7950   -1.3032   -0.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -0.0256   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9433    0.3411   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9768    1.1368    1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1683    1.4839    1.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3997    1.0474    1.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5856    1.3581    1.9531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4531    0.2515    0.1790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7001   -0.1974   -0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7671   -1.0171   -1.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -0.0899   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789   -2.2005   -0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665   -1.2927   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873   -1.3192    0.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -0.0888   -1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9092    0.7929   -0.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9525    1.4812    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403    2.1143    2.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5127    1.9453    2.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -0.3760   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -1.8646   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711   -1.4555   -1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685   -0.7219   -1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
 11 23  1  0
M  END
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PDB for #<Metabolite:0x0000560be06822d8>

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       2.667  -3.080   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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   11                                                            
CONECT    3    1    7                                                       
CONECT    4    5    7                                                       
CONECT    5    4    8                                                       
CONECT    6    7    9                                                       
CONECT    7    3    4    6                                                  
CONECT    8    5    9   10                                                  
CONECT    9    6    8   11                                                  
CONECT   10    8                                                            
CONECT   11    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x0000560be06822d8>

COMPND    HMDB0040175
HETATM    1  C1  UNL     1       2.795  -1.303  -0.307  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.187  -0.026  -0.819  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.943   0.341  -0.088  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.977   1.137   1.048  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.168   1.484   1.735  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.400   1.047   1.312  1.00  0.00           C  
HETATM    7  O1  UNL     1      -2.586   1.358   1.953  1.00  0.00           O  
HETATM    8  C7  UNL     1      -1.453   0.252   0.179  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.700  -0.197  -0.259  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.767  -1.017  -1.424  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.301  -0.090  -0.501  1.00  0.00           C  
HETATM   12  H1  UNL     1       2.279  -2.201  -0.726  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.867  -1.293  -0.605  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.787  -1.319   0.807  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.029  -0.089  -1.906  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.909   0.793  -0.638  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.953   1.481   1.381  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.140   2.114   2.635  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.513   1.945   2.783  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.500  -0.376  -2.295  1.00  0.00           H  
HETATM   21  H10 UNL     1      -2.057  -1.865  -1.339  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.771  -1.455  -1.529  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.368  -0.722  -1.396  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4    4   11
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7    8
CONECT    7   19
CONECT    8    9   11   11
CONECT    9   10
CONECT   10   20   21   22
CONECT   11   23
END
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SMILES for #<Metabolite:0x0000560be06822d8>

CCC1=CC(OC)=C(O)C=C1
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INCHI for #<Metabolite:0x0000560be06822d8>

InChI=1S/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3
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Synonyms
ValueSource
P-EthylguaiacolMetaCyc, HMDB
1-Hydroxy-2-methoxy-4-ethylbenzeneHMDB
2-Methoxy-4-ethylphenolHMDB, MeSH
4-Ethyl guiacolHMDB
4-Ethyl-2-methoxy-phenolHMDB
4-Ethyl-2-methoxyphenol (4-ethylguaiacol)HMDB
4-Ethyl-2-metoxy phenolHMDB
4-Ethyl-guaiacolHMDB
4-EthylguaiacolHMDB, MeSH
4-Hydroxy-3-methoxy ethylbenzeneHMDB
4-Hydroxy-3-methoxyethylbenzeneHMDB
4-Hydroxy-3-methoxyphenylethaneHMDB
Ethylguiacol (4-ethyl-2-methoxyphenol)HMDB
FEMA 2436HMDB
Guaiacol, 4-ethylHMDB
Guaiacyl ethaneHMDB
HomocresolHMDB
P-Ethyl-2-methoxyphenolHMDB
Phenol, 2-methoxy-4-ethylHMDB
Molecular FormulaC9H12O2
Average Mass152.1904
Monoisotopic Mass152.083729628
IUPAC Name4-ethyl-2-methoxyphenol
Traditional Name4-ethylguaiacol
CAS Registry Number2785-89-9
SMILES
CCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C9H12O2/c1-3-7-4-5-8(10)9(6-7)11-2/h4-6,10H,3H2,1-2H3
InChI KeyCHWNEIVBYREQRF-UHFFFAOYSA-N