Showing metabocard for Acetovanillone (MMDBc0033590)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:54:49 UTC
Update Date2022-08-31 22:36:54 UTC
Metabolite IDMMDBc0033590
Metabolite Identification
Common NameAcetovanillone
DescriptionAcetovanillone, also known as acetoguaiacon or apocynine, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Acetovanillone is a faint, sweet, and vanillin tasting compound. Acetovanillone is found, on average, in the highest concentration within white wine. Acetovanillone has also been detected, but not quantified in, a few different foods, such as asparagus (Asparagus officinalis), corns (Zea mays), and garden onions (Allium cepa). This could make acetovanillone a potential biomarker for the consumption of these foods. Acetovanillone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Acetovanillone.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f1222482048>


  Mrv1652309272007372D          

 12 12  0  0  0  0            999 V2000
 9969.4909 9968.8441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9972.3447 9970.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9973.0569 9970.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.3447 9971.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.6338 9970.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.9193 9970.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.2047 9970.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.2047 9969.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.9191 9968.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.6338 9969.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.9191 9968.0193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.6314 9967.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
  5  2  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f1222482048>

HMDB0247918
     RDKit          3D
Acetovanillone
 22 22  0  0  0  0  0  0  0  0999 V2000
    2.9102   -0.7847    1.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7122   -0.4693    0.2419 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4598   -0.1708   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848   -0.1810    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949    0.1163    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111    0.0977    1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3798    0.4063    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285   -0.1824    2.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102    0.4233   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315    0.4372   -2.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2495    0.1374   -1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468    0.1417   -2.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382   -1.2417    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8256    0.0986    2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -1.5830    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5273   -0.4204    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    1.5152    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082   -0.0388    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867   -0.0056   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0716    0.6630   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    0.6785   -3.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349    0.3626   -3.3914 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  1  0
  6  7  1  0
  6  8  2  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f1222482048>


  Mrv1652309272007372D          

 12 12  0  0  0  0            999 V2000
 9969.4909 9968.8441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9972.3447 9970.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9973.0569 9970.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9972.3447 9971.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.6338 9970.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.9193 9970.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.2047 9970.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.2047 9969.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.9191 9968.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9971.6338 9969.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9970.9191 9968.0193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9971.6314 9967.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
  5  2  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033590

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3

> <INCHI_KEY>
DFYRUELUNQRZTB-UHFFFAOYSA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.1739

> <EXACT_MASS>
166.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.942995750186867

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
1.0696567473333332

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.559514731409475

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.274969994019505

> <JCHEM_PKA_STRONGEST_BASIC>
-4.897013421414668

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
44.90490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apocynin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f1222482048>

HMDB0247918
     RDKit          3D
Acetovanillone
 22 22  0  0  0  0  0  0  0  0999 V2000
    2.9102   -0.7847    1.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7122   -0.4693    0.2419 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4598   -0.1708   -0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848   -0.1810    0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949    0.1163    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0111    0.0977    1.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3798    0.4063    0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8285   -0.1824    2.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102    0.4233   -1.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315    0.4372   -2.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2495    0.1374   -1.5695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3468    0.1417   -2.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9382   -1.2417    1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8256    0.0986    2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -1.5830    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5273   -0.4204    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    1.5152    0.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1082   -0.0388    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5867   -0.0056   -0.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0716    0.6630   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875    0.6785   -3.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349    0.3626   -3.3914 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  1  0
  6  7  1  0
  6  8  2  0
  5  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
M  END
Download

PDB for #<Metabolite:0x00007f1222482048>

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  O   UNK     0    8609.7168608.509   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8615.0448611.582   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8616.3738610.813   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8615.0448613.118   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8613.7168610.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8612.3838611.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8611.0498610.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8611.0498609.275   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8612.3828608.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8613.7168609.275   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8612.3828606.969   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8613.7128606.202   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    3    4    5                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    6   10    2                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    1                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   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:0x00007f1222482048>

COMPND    HMDB0247918
HETATM    1  C1  UNL     1       2.910  -0.785   1.607  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.712  -0.469   0.242  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.460  -0.171  -0.249  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.385  -0.181   0.609  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.895   0.116   0.144  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.011   0.098   1.074  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.380   0.406   0.619  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.829  -0.182   2.284  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.110   0.423  -1.167  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.032   0.437  -2.045  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.250   0.137  -1.570  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.347   0.142  -2.415  1.00  0.00           O  
HETATM   13  H1  UNL     1       3.938  -1.242   1.663  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.826   0.099   2.266  1.00  0.00           H  
HETATM   15  H3  UNL     1       2.185  -1.583   1.897  1.00  0.00           H  
HETATM   16  H4  UNL     1       0.527  -0.420   1.650  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.565   1.515   0.547  1.00  0.00           H  
HETATM   18  H6  UNL     1      -4.108  -0.039   1.320  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.587  -0.006  -0.405  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.072   0.663  -1.594  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.187   0.678  -3.085  1.00  0.00           H  
HETATM   22  H10 UNL     1       2.235   0.363  -3.391  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   16
CONECT    5    6    9    9
CONECT    6    7    8    8
CONECT    7   17   18   19
CONECT    9   10   20
CONECT   10   11   11   21
CONECT   11   12
CONECT   12   22
END
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SMILES for #<Metabolite:0x00007f1222482048>

COC1=CC(=CC=C1O)C(C)=O
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INCHI for #<Metabolite:0x00007f1222482048>

InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
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Synonyms
ValueSource
1-(4-Hydroxy-3-methoxyphenyl)ethanoneChEBI
4'-Hydroxy-3'-methoxyacetophenoneChEBI
4-Acetyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxyphenyl methyl ketoneChEBI
AcetoguaiaconChEBI
AcetoguaiaconeChEBI
4-Hydroxy-3-methoxyacetophenoneHMDB
ApocynineHMDB
ApocyninHMDB
2-Methoxy-4-acetylphenolHMDB
3-Methoxy-4-hydroxyphenylethanoneHMDB
3'-Methoxy-4'-hydroxyacetophenoneHMDB
3’-methoxy-4’-hydroxyacetophenoneHMDB
4-AcetylguaiacolHMDB
4’-hydroxy-3’-methoxyacetophenoneHMDB
AcetoguaiacolHMDB
AcetoguaiconeHMDB
AcetovanilloneChEBI
Molecular FormulaC9H10O3
Average Mass166.1739
Monoisotopic Mass166.062994186
IUPAC Name1-(4-hydroxy-3-methoxyphenyl)ethan-1-one
Traditional Nameapocynin
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC=C1O)C(C)=O
InChI Identifier
InChI=1S/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
InChI KeyDFYRUELUNQRZTB-UHFFFAOYSA-N