Showing metabocard for Syringaldehyde (MMDBc0033714)

Plant
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-19 05:00:07 UTC
Update Date2025-10-07 16:04:13 UTC
Metabolite IDMMDBc0033714
Metabolite Identification
Common NameSyringaldehyde
DescriptionSyringaldehyde is a phenylpropanoid compound known for its role as a phytoalexin in plants. Its chemical structure features a methoxy group and an aldehyde functional group attached to a benzene ring, contributing to its reactivity and biological activities. In the context of plant defense, syringaldehyde has been shown to induce immune-related gene expression in eggplant leaves and enhance resistance against pathogens, such as late blight in potatoes, when applied exogenously (PMID:41032367 ). Notably, its protective efficacy is amplified in genetically modified potato plants overexpressing SmTPS28, indicating a synergistic relationship in nonhost resistance mechanisms (PMID:41032367 ). Additionally, syringaldehyde has been utilized in the preparation of Schiff base-type oleogels, demonstrating its versatility in material science (PMID:41030385 ). It also serves as a strong ligand for various plant odorant-binding proteins, highlighting its potential role in plant-insect interactions (PMID:40915826 ). Furthermore, studies on the ozonolysis of phenolic aldehydes, including syringaldehyde, provide insights into its environmental behavior and reactivity under different conditions (PMID:40829472 ). Overall, syringaldehyde exemplifies a compound with significant implications in both plant biology and material applications.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f8af5318cd8>


  Mrv1652309272007432D          

 13 13  0  0  0  0            999 V2000
    2.7241    1.5174    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
   -0.8481    0.2798    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    1.9298    0.0000 O   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
    1.2951    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
   -0.1337    0.6923    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
    0.5806    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -0.5451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 10  5  1  0  0  0  0
  6  2  1  0  0  0  0
  6 11  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
  9  3  1  0  0  0  0
  2  1  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f8af5318cd8>

HMDB0258653
     RDKit          3D
Syringaldehyde
 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.3549   -1.6758   -0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9749   -1.8640   -0.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317   -0.8718   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871    0.4648   -0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236    1.4369   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    2.8281   -0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0382    3.1819   -0.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259    1.0769   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015   -0.2440   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181   -0.6101   -0.0826 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079    0.2558   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.2009   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243   -2.5756   -0.1575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6637   -0.9360   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8086   -1.3986    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8264   -2.6400   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4608    0.6944   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967    3.6313   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270    1.8962   -0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4988   -0.2442    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4881    1.2529    0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    0.4021   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5968   -2.8604   -0.1129 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  2  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  8 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
 13 23  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f8af5318cd8>


  Mrv1652309272007432D          

 13 13  0  0  0  0            999 V2000
    2.7241    1.5174    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
   -0.8481    0.2798    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    1.9298    0.0000 O   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
    1.2951    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
   -0.1337    0.6923    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
    0.5806    1.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806   -0.5451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1338   -0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 10  5  1  0  0  0  0
  6  2  1  0  0  0  0
  6 11  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
  9  3  1  0  0  0  0
  2  1  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033714

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3

> <INCHI_KEY>
KCDXJAYRVLXPFO-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.764642136235814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,5-dimethoxybenzaldehyde

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.0668403076666666

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.243570534496414

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6076316073321335

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
47.5493

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.68e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
syringaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f8af5318cd8>

HMDB0258653
     RDKit          3D
Syringaldehyde
 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.3549   -1.6758   -0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9749   -1.8640   -0.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317   -0.8718   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3871    0.4648   -0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236    1.4369   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8355    2.8281   -0.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0382    3.1819   -0.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259    1.0769   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015   -0.2440   -0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6181   -0.6101   -0.0826 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7079    0.2558   -0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.2009   -0.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6243   -2.5756   -0.1575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6637   -0.9360   -1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8086   -1.3986    0.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8264   -2.6400   -0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4608    0.6944   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967    3.6313   -0.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270    1.8962   -0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4988   -0.2442    0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4881    1.2529    0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    0.4021   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5968   -2.8604   -0.1129 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  2  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  0
  8 19  1  0
 11 20  1  0
 11 21  1  0
 11 22  1  0
 13 23  1  0
M  END
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PDB for #<Metabolite:0x00007f8af5318cd8>

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       5.085   2.832   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.751   3.602   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.583   0.522   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.917   2.832   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.583   3.602   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.418   2.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.418   1.292   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.084   0.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.250   1.292   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.084   3.602   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.084  -1.018   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.250  -1.788   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    6    1                                                       
CONECT    3    9                                                            
CONECT    4    5                                                            
CONECT    5    4   10                                                       
CONECT    6    2   11    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10    3                                                  
CONECT   10    5    9   11                                                  
CONECT   11    6   10                                                       
CONECT   12    8   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x00007f8af5318cd8>

COMPND    HMDB0258653
HETATM    1  C1  UNL     1      -3.355  -1.676  -0.338  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.975  -1.864  -0.276  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.032  -0.872  -0.241  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.387   0.465  -0.266  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.424   1.437  -0.229  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.835   2.828  -0.257  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.038   3.182  -0.312  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.926   1.077  -0.168  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.302  -0.244  -0.143  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.618  -0.610  -0.083  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.708   0.256  -0.040  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.320  -1.201  -0.180  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.624  -2.576  -0.157  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.664  -0.936  -1.129  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.809  -1.399   0.637  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.826  -2.640  -0.637  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.461   0.694  -0.314  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.097   3.631  -0.229  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.627   1.896  -0.142  1.00  0.00           H  
HETATM   20  H7  UNL     1       4.499  -0.244   0.592  1.00  0.00           H  
HETATM   21  H8  UNL     1       3.488   1.253   0.390  1.00  0.00           H  
HETATM   22  H9  UNL     1       4.194   0.402  -1.029  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.597  -2.860  -0.113  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   17
CONECT    5    6    8    8
CONECT    6    7    7   18
CONECT    8    9   19
CONECT    9   10   12   12
CONECT   10   11
CONECT   11   20   21   22
CONECT   12   13
CONECT   13   23
END
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SMILES for #<Metabolite:0x00007f8af5318cd8>

COC1=CC(C=O)=CC(OC)=C1O
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INCHI for #<Metabolite:0x00007f8af5318cd8>

InChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3
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Synonyms
ValueSource
SinapaldehydeChEMBL
SYALMeSH
2,6-Dimethoxy-4-formylphenolMeSH
3,5-Dimethoxy-4-hydroxybenzaldehydeMeSH
4-Hydroxy-3,5-dimethoxybenzaldehydePhytoBank
4-Formyl-2,6-dimethoxyphenolPhytoBank
4-FormylsyringolPhytoBank
Cedar aldehydePhytoBank
Gallaldehyde 3,5-dimethyl etherPhytoBank
Syringic aldehydePhytoBank
3,5-Dimethoxy-4-hydroxy-benzaldehydePhytoBank
Molecular FormulaC9H10O4
Average Mass182.1733
Monoisotopic Mass182.057908808
IUPAC Name4-hydroxy-3,5-dimethoxybenzaldehyde
Traditional Namesyringaldehyde
CAS Registry Number134-96-3
SMILES
COC1=CC(C=O)=CC(OC)=C1O
InChI Identifier
InChI=1S/C9H10O4/c1-12-7-3-6(5-10)4-8(13-2)9(7)11/h3-5,11H,1-2H3
InChI KeyKCDXJAYRVLXPFO-UHFFFAOYSA-N