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Showing NP-Card for Acetovanillone (NP0002802)

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Record Information
Version1.0
Created at2020-11-23 19:40:49 UTC
Updated at2024-04-19 10:08:45 UTC
NP-MRD IDNP0002802
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetovanillone
Provided ByBMRBBMRB logo
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 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. Acetovanillone is found in Abies nephrolepis, Abies spectabilis, Aglaia foveolata, Anastatica hierochuntica, Baccharis tola, Basella alba, Boophane disticha , Vincetoxicum hirundinaria, Cynanchum wilfordii, Fabiana imbricata, Hyoscyamus albus, Imperata cylindrica, Iris domestica, Iris germanica, Iris nigricans, Iris pallida, Iris tingitana, Lagochilus leiacanthus, Ligularia stenocephala, Mansonia gagei, Ophiocordyceps sinensis, Paeonia lactiflora, Paeonia rockii, Paeonia suffruticosa ANDREWS , Picea glauca, Picrorhiza kurrooa, Pinus wallichiana, Polygala senega, Populus euphratica, Pyrola americana, Sargentodoxa cuneata, Senecio filaginoides, Spinacia oleracea, Stellaria dichotoma, Thymus broussonetti, Thymus maroccanus, Thymus praecos, Vincetoxicum atratum, Vitis vinifera, Zea mays, Zingiber officinale and Ziziphora clinopodioides. It was first documented in 2008 (PMID: 17984079). Based on a literature review a small amount of articles have been published on Acetovanillone (PMID: 21848266) (PMID: 21954959) (PMID: 24870309) (PMID: 34322910) (PMID: 33969557) (PMID: 33748917).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002802 (Acetovanillone)


     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    3.2318   -1.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -0.0665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3751   -0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0532   -0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641   -1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5924   -0.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -2.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3707    1.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598    2.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1686    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795    2.8655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -1.2151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -1.8500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5493   -2.9986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926   -2.0824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505   -2.1365    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    0.7202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0208   -0.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990    1.7658    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    3.7817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078    2.4074    0.0000 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  1
  1 14  1  0
  1 15  1  0
  4 16  1  0
  7 17  1  1
  7 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
M  END
Download

3D MOL for NP0002802 (Acetovanillone)

NP0002802
     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    2.4695   -1.5701    0.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144   -0.2184    0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    0.4265    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -0.2492    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913    0.4171   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -0.2721   -0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007   -1.7497   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4989    0.3156   -0.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1472    1.7764   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0234    2.4822   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1804    1.7885   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3518    2.5216    0.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1961   -2.1527   -0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9222   -1.9533    1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527   -1.7809    1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.3024    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198   -2.1817   -0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.1700   -0.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838   -2.0106    0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0499    2.2806   -0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554    3.5442   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2103    2.0585    0.3984 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 NP0002802 (Acetovanillone)


     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    3.2318   -1.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -0.0665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4860    0.3915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3751   -0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0532   -0.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641   -1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5924   -0.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -2.6323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3707    1.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2598    2.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1686    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795    2.8655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978   -1.2151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658   -1.8500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5493   -2.9986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6926   -2.0824    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0505   -2.1365    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343    0.7202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0208   -0.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990    1.7658    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    3.7817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7078    2.4074    0.0000 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  1
  1 14  1  0
  1 15  1  0
  4 16  1  0
  7 17  1  1
  7 18  1  0
  7 19  1  0
  9 20  1  0
 10 21  1  0
 12 22  1  0
M  END
> <DATABASE_ID>
NP0002802

> <DATABASE_NAME>
NP-MRD

> <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 NP0002802 (Acetovanillone)

NP0002802
     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
    2.4695   -1.5701    0.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3144   -0.2184    0.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    0.4265    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0384   -0.2492    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913    0.4171   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -0.2721   -0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5007   -1.7497   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4989    0.3156   -0.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1472    1.7764   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0234    2.4822   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1804    1.7885   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3518    2.5216    0.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1961   -2.1527   -0.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9222   -1.9533    1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527   -1.7809    1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.3024    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198   -2.1817   -0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6183   -2.1700   -0.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838   -2.0106    0.7954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0499    2.2806   -0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554    3.5442   -0.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2103    2.0585    0.3984 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 NP0002802 (Acetovanillone)

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 NP0002802 (Acetovanillone)

COMPND    NP0002802
HETATM    1  C1  UNL     1       2.469  -1.570   0.827  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.314  -0.218   0.569  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.167   0.427   0.203  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.038  -0.249   0.041  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.191   0.417  -0.331  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.455  -0.272  -0.504  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.501  -1.750  -0.272  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.499   0.316  -0.838  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.147   1.776  -0.544  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.023   2.482  -0.395  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.180   1.788  -0.018  1.00  0.00           C  
HETATM   12  O3  UNL     1       2.352   2.522   0.127  1.00  0.00           O  
HETATM   13  H1  UNL     1       2.196  -2.153  -0.091  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.922  -1.953   1.702  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.553  -1.781   1.002  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.040  -1.302   0.213  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.420  -2.182  -0.727  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.618  -2.170  -0.766  1.00  0.00           H  
HETATM   19  H7  UNL     1      -2.484  -2.011   0.795  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.050   2.281  -0.832  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.055   3.544  -0.562  1.00  0.00           H  
HETATM   22  H10 UNL     1       3.210   2.058   0.398  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 NP0002802 (Acetovanillone)

COC1=CC(=CC=C1O)C(C)=O
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INCHI for NP0002802 (Acetovanillone)

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
Chemical FormulaC9H10O3
Average Mass166.1739 Da
Monoisotopic Mass166.06299 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-02-02View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, DMSO, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies nephrolepisLOTUS Database
Abies spectabilisLOTUS Database
Aglaia foveolataLOTUS Database
Allium cepaKNApSAcK Database
Amelanchier alnifoliaKNApSAcK Database
Anastatica hierochunticaLOTUS Database
Apocynum androsaemifoliumKNApSAcK Database
Apocynum cannabinumKNApSAcK Database
Baccharis tolaLOTUS Database
Basella albaLOTUS Database
Boophane disticha-
Cynanchum vincetoxicumLOTUS Database
Cynanchum wilfordiiLOTUS Database
Echinocereus engelmanniiKNApSAcK Database
Engelhardia roxburghianaKNApSAcK Database
Fabiana imbricataLOTUS Database
Hyoscyamus albusLOTUS Database
Imperata cylindricaLOTUS Database
Iris domesticaLOTUS Database
Iris germanicaLOTUS Database
Iris germanica L.KNApSAcK Database
Iris nigricansLOTUS Database
Iris pallidaLOTUS Database
Iris spp.KNApSAcK Database
Iris tingitanaLOTUS Database
Lagochilus leiacanthusLOTUS Database
Ligularia stenocephalaLOTUS Database
Mammillaria runyoniiKNApSAcK Database
Mansonia gageiLOTUS Database
Mansonia gagei DRUMM.KNApSAcK Database
Ophiocordyceps sinensisLOTUS Database
Paeonia lactifloraLOTUS Database
Paeonia rockiiLOTUS Database
Paeonia suffruticosaPlant
Paeonia suffruticosa ANDREWSKNApSAcK Database
Photinia davidianaKNApSAcK Database
Picea glaucaLOTUS Database
Picrorhiza kurroaKNApSAcK Database
Picrorhiza kurrooaLOTUS Database
Pinus wallichianaLOTUS Database
Polygala senegaLOTUS Database
Populus euphraticaLOTUS Database
Posidonia oceanicaKNApSAcK Database
Pyrola americanaLOTUS Database
Sargentodoxa cuneataLOTUS Database
Senecio filaginoidesLOTUS Database
Spinacia oleraceaLOTUS Database
Stellaria dichotomaLOTUS Database
Thymus broussonettiPlant
Thymus maroccanusPlant
Thymus praecosPlant
Vincetoxicum atratumLOTUS Database
Viscum coloratumKNApSAcK Database
Vitis viniferaLOTUS Database
Zea maysLOTUS Database
Zea mays L.KNApSAcK Database
Zingiber officinaleLOTUS Database
Ziziphora clinopodioidesLOTUS Database
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point113.00 to 115.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point263.00 to 265.00 °C. @ 17.00 mm HgThe Good Scents Company Information System
Water Solubility5000 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP1.389 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP1.62ALOGPS
logP1.07ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)8.27ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.9 m³·mol⁻¹ChemAxon
Polarizability16.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0247918
DrugBank IDDB12618
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012055
KNApSAcK IDC00002689
Chemspider ID21106900
KEGG Compound IDC11380
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkApocynin
METLIN IDNot Available
PubChem Compound2214
PDB IDNot Available
ChEBI ID2781
Good Scents IDrw1057511
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Yang ML, Kuo PC, Hwang TL, Wu TS: Anti-inflammatory principles from Cordyceps sinensis. J Nat Prod. 2011 Sep 23;74(9):1996-2000. doi: 10.1021/np100902f. Epub 2011 Aug 17. [PubMed:21848266 ]
  3. Mencherini T, Picerno P, Festa M, Russo P, Capasso A, Aquino R: Triterpenoid constituents from the roots of Paeonia rockii ssp. rockii. J Nat Prod. 2011 Oct 28;74(10):2116-21. doi: 10.1021/np200359v. Epub 2011 Sep 28. [PubMed:21954959 ]
  4. Majumdar S, Lukk T, Solbiati JO, Bauer S, Nair SK, Cronan JE, Gerlt JA: Roles of small laccases from Streptomyces in lignin degradation. Biochemistry. 2014 Jun 24;53(24):4047-58. doi: 10.1021/bi500285t. [PubMed:24870309 ]
  5. Di Lella S, La Porta N, Tognetti R, Lombardi F, Nardin T, Larcher R: White rot fungal impact on the evolution of simple phenols during decay of silver fir wood by UHPLC-HQOMS. Phytochem Anal. 2021 Jul 28. doi: 10.1002/pca.3077. [PubMed:34322910 ]
  6. Abd El-Ghafar OAM, Hassanein EHM, Sayed AM, Rashwan EK, Shalkami AS, Mahmoud AM: Acetovanillone prevents cyclophosphamide-induced acute lung injury by modulating PI3K/Akt/mTOR and Nrf2 signaling in rats. Phytother Res. 2021 Aug;35(8):4499-4510. doi: 10.1002/ptr.7153. Epub 2021 May 9. [PubMed:33969557 ]
  7. Slama N, Mankai H, Limam F: Streptomyces tunisiensis DSM 42037 mediated bioconversion of ferulic acid released from barley bran. World J Microbiol Biotechnol. 2021 Mar 22;37(4):70. doi: 10.1007/s11274-021-03031-4. [PubMed:33748917 ]
  8. Hassanein EHM, Abd El-Ghafar OAM, Ahmed MA, Sayed AM, Gad-Elrab WM, Ajarem JS, Allam AA, Mahmoud AM: Edaravone and Acetovanillone Upregulate Nrf2 and PI3K/Akt/mTOR Signaling and Prevent Cyclophosphamide Cardiotoxicity in Rats. Drug Des Devel Ther. 2020 Nov 30;14:5275-5288. doi: 10.2147/DDDT.S281854. eCollection 2020. [PubMed:33299300 ]