Showing metabocard for Coniferyl aldehyde (MMDBc0001587)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-05-14 19:49:04 UTC
Update Date2025-01-16 23:20:58 UTC
Metabolite IDMMDBc0001587
Metabolite Identification
Common NameConiferyl aldehyde
DescriptionConiferaldehyde (CAS: 458-36-6), also known as 4-hydroxy-3-methoxycinnamaldehyde or ferulaldehyde, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, coniferaldehyde is found, on average, in the highest concentration within sherries. Coniferaldehyde has also been detected, but not quantified in, several different foods, such as highbush blueberries, lima beans, Chinese cabbages, loquats, and greenthread tea. This could make coniferaldehyde a potential biomarker for the consumption of these foods. BioTransformer predicts that coniferaldehyde is a product of caffeic aldehyde metabolism via a catechol-O-methylation-pattern2 reaction catalyzed by the enzyme catechol O-methyltransferase (PMID: 30612223 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fca0f319710>


  Mrv1652309272007382D          

 13 13  0  0  0  0            999 V2000
10000.694810000.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.409910000.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.127110000.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.842310000.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.828110000.8120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.107610000.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8281 9999.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.975610000.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.261110000.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.546610000.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5465 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2610 9999.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9756 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
 11  7  1  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fca0f319710>

HMDB0141782
     RDKit          3D
Coniferaldehyde
 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.4270    1.9703    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6803    0.6683    0.2239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207   -0.1787   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    0.2274    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426   -0.6149   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462   -0.2262   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    0.9392    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0027    1.2398    0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252    2.3710    0.9353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4092   -1.8757   -0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990   -2.2679   -0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498   -1.4304   -0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2770   -1.8057   -0.7117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0048    2.6474   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3651    2.4458    1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    1.9569    1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1199    1.2242    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9415   -0.9424   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    1.6697    0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7776    0.5495    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -2.5680   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1600   -3.2603   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511   -2.7393   -1.0642 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
  7  8  1  0
  8  9  2  0
  5 10  2  0
 10 11  1  0
 11 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
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fca0f319710>


  Mrv1652309272007382D          

 13 13  0  0  0  0            999 V2000
10000.694810000.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.409910000.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.127110000.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.842310000.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.828110000.8120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.107610000.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8281 9999.1579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.975610000.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.261110000.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.546610000.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5465 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2610 9999.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9756 9999.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  6  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
 11  7  1  0  0  0  0
 10  5  1  0  0  0  0
  1  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001587

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C=CC(\C=C\C=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+

> <INCHI_KEY>
DKZBBWMURDFHNE-NSCUHMNNSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.379866786522083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.5162334203333336

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.515601076850212

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2891797272383405

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
50.57860000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coniferaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fca0f319710>

HMDB0141782
     RDKit          3D
Coniferaldehyde
 23 23  0  0  0  0  0  0  0  0999 V2000
   -2.4270    1.9703    0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6803    0.6683    0.2239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6207   -0.1787   -0.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2983    0.2274    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426   -0.6149   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1462   -0.2262   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    0.9392    0.3794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0027    1.2398    0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3252    2.3710    0.9353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4092   -1.8757   -0.7002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8990   -2.2679   -0.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498   -1.4304   -0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2770   -1.8057   -0.7117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0048    2.6474   -0.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3651    2.4458    1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    1.9569    1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1199    1.2242    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9415   -0.9424   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    1.6697    0.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7776    0.5495    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -2.5680   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1600   -3.2603   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511   -2.7393   -1.0642 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
  7  8  1  0
  8  9  2  0
  5 10  2  0
 10 11  1  0
 11 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
  7 19  1  0
  8 20  1  0
 10 21  1  0
 11 22  1  0
 13 23  1  0
M  END
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PDB for #<Metabolite:0x00007fca0f319710>

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  C   UNK     0    8667.9648668.182   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.2988667.415   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.6378668.182   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8671.9728667.415   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8662.6128668.182   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8661.2688667.411   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8662.6128665.095   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8666.6218667.411   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.2878668.181   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.9548667.411   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.9538665.871   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.2878665.101   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.6218665.871   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6   10                                                       
CONECT    6    5                                                            
CONECT    7   11                                                            
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    5                                                  
CONECT   11   10   12    7                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x00007fca0f319710>

COMPND    HMDB0141782
HETATM    1  C1  UNL     1      -2.427   1.970   0.716  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.680   0.668   0.224  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.621  -0.179  -0.083  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.298   0.227   0.083  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.743  -0.615  -0.223  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.146  -0.226  -0.063  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.562   0.939   0.379  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.003   1.240   0.507  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.325   2.371   0.935  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.409  -1.876  -0.700  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.899  -2.268  -0.861  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.950  -1.430  -0.557  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.277  -1.806  -0.712  1.00  0.00           O  
HETATM   14  H1  UNL     1      -2.005   2.647  -0.056  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.365   2.446   1.070  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.674   1.957   1.557  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.120   1.224   0.459  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.941  -0.942  -0.324  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.817   1.670   0.646  1.00  0.00           H  
HETATM   20  H7  UNL     1       4.778   0.550   0.256  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.203  -2.568  -0.952  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.160  -3.260  -1.236  1.00  0.00           H  
HETATM   23  H10 UNL     1      -3.451  -2.739  -1.064  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   10   10
CONECT    6    7    7   18
CONECT    7    8   19
CONECT    8    9    9   20
CONECT   10   11   21
CONECT   11   12   12   22
CONECT   12   13
CONECT   13   23
END
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SMILES for #<Metabolite:0x00007fca0f319710>

COC1=C(O)C=CC(\C=C\C=O)=C1
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INCHI for #<Metabolite:0x00007fca0f319710>

InChI=1S/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+
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Synonyms
ValueSource
(e)-ConiferaldehydeChEBI
4-Hydroxy-3-methoxycinnamaldehydeChEBI
FerulaldehydeChEBI
ConiferylaldehydeHMDB
trans-Coniferyl aldehydeHMDB
Coniferyl aldehydeHMDB
Coniferaldehyde, (e)-isomerHMDB
4-HM-CAHMDB
(2E)-3-(4-Hydroxy-3-methoxyphenyl)-2-propenalHMDB
(2E)-4-Hydroxy-3-methoxycinnamaldehydeHMDB
(e)-3-(4-Hydroxy-3-methoxyphenyl)acrylaldehydeHMDB
(e)-3-(4-Hydroxy-m-methoxyphenyl)prop-2-enalHMDB
(e)-Coniferyl aldehydeHMDB
(e)-FerulaldehydeHMDB
2-Methoxy-4-(3-oxo-1-propenyl)phenolHMDB
3-(4-Hydroxy-3-methoxyphenyl)-2-propenalHMDB
3-(4-Hydroxy-3-methoxyphenyl)acroleinHMDB
3-(4-Hydroxy-3-methoxyphenyl)propenalHMDB
3-Methoxy-4-hydroxycinnamaldehydeHMDB
4-Hydroxy-3-methoxy-trans-cinnamaldehydeHMDB
4-Hydroxy-3-methoxyzimtaldehydeHMDB
e-Coniferyl aldehydeHMDB
Ferulic aldehydeHMDB
Ferulyl aldehydeHMDB
p-ConiferaldehydeHMDB
trans-ConiferaldehydeHMDB
trans-FerulaldehydeHMDB
ConiferaldehydeChEBI
Molecular FormulaC10H10O3
Average Mass178.1846
Monoisotopic Mass178.062994186
IUPAC Name(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enal
Traditional Nameconiferaldehyde
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(\C=C\C=O)=C1
InChI Identifier
InChI=1S/C10H10O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h2-7,12H,1H3/b3-2+
InChI KeyDKZBBWMURDFHNE-NSCUHMNNSA-N