Showing metabocard for Acetovanillone (MMDBc0033590)

Plant
Pharmaceutical
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-19 04:54:49 UTC
Update Date2025-10-07 16:04:12 UTC
Metabolite IDMMDBc0033590
Metabolite Identification
Common NameAcetovanillone
DescriptionAcetovanillone is a phenolic compound classified as a vanillin derivative containing an acetyl side chain. Its chemical structure features a methoxy group and a carbonyl group adjacent to a phenolic hydroxyl, making it a key metabolite in the degradation pathways of lignin, a complex plant polymer. The depolymerization of lignin generates various aromatic products, including acetovanillone, which can be utilized in biochemical processes. Interestingly, while the Alphaproteobacterium Novosphingobium aromaticivorans DSM12444 can metabolize several chemically modified aromatics derived from lignin, it does not utilize acetovanillone as a growth substrate (PMID:40840623 ). However, specific genetic modifications in bacterial strains have shown a significant increase in the phosphorylation rate of acetovanillone, indicating potential pathways for its metabolism (PMID:40840623 ). Moreover, acetovanillone is part of a broader network of aromatic compounds that exhibit varying antioxidant activities, which are influenced by their structural characteristics (PMID:40769347 ). The breakdown of lignin into acetovanillone and other phenolic monomers is facilitated by free-radical reactions, highlighting its role in the bioconversion of lignin into valuable chemical feedstocks (PMID:40686944 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9aa8a354e0>


  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:0x00007f9aa8a354e0>

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:0x00007f9aa8a354e0>


  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

$$$$
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3D-SDF for #<Metabolite:0x00007f9aa8a354e0>

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
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PDB for #<Metabolite:0x00007f9aa8a354e0>

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:0x00007f9aa8a354e0>

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:0x00007f9aa8a354e0>

COC1=CC(=CC=C1O)C(C)=O
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INCHI for #<Metabolite:0x00007f9aa8a354e0>

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