Showing metabocard for Vanillin (MMDBc0033726)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 05:00:37 UTC
Update Date2024-04-30 20:15:56 UTC
Metabolite IDMMDBc0033726
Metabolite Identification
Common NameVanillin
DescriptionVanillin, also known as vanillaldehyde or 5-bromovanillin, 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. Vanillin exists in all living species, ranging from bacteria to plants to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns (Zea mays), ryes (Secale cereale), and sherry and in a lower concentration in spirit, cocoa powder, and highbush blueberries (Vaccinium corymbosum). Vanillin has also been detected, but not quantified in, several different foods, such as nutmegs (Myristica fragrans), rowanberries (Sorbus aucuparia), domestic pigs (Sus scrofa domestica), narrowleaf cattails (Typha angustifolia), and scarlet beans (Phaseolus coccineus). This could make vanillin a potential biomarker for the consumption of these foods. Vanillin 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 significant number of articles have been published on Vanillin.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fe29ed7a338>


  Mrv1652309272007342D          

 11 11  0  0  0  0            999 V2000
 9980.8636 9979.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1527 9978.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4383 9979.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7236 9978.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7236 9977.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4381 9977.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1527 9977.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.0107 9977.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.5766 9978.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4380 9976.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1508 9976.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  2  1  0  0  0  0
  2  1  1  0  0  0  0
  5  8  1  0  0  0  0
  1  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fe29ed7a338>

HMDB0012308
     RDKit          3D
Vanillin
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.2700   -0.9415   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.2379   -0.9871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7213    0.3403   -0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -0.7169   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3592   -0.6118    0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.7283    0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368   -1.5760    1.2647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201    0.6029    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    1.6543    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393    1.5374    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425    2.6147    0.2447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -0.9236   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822   -1.0640   -2.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0312   -1.8666   -1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340   -1.6652   -0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310   -2.6473    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480    0.6815    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740    2.5791    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    3.4932    0.7007 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  2  0
 10 11  1  0
 10  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fe29ed7a338>


  Mrv1652309272007342D          

 11 11  0  0  0  0            999 V2000
 9980.8636 9979.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1527 9978.6010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4383 9979.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7236 9978.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.7236 9977.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4381 9977.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1527 9977.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9978.0107 9977.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9981.5766 9978.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.4380 9976.5401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9980.1508 9976.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  2  1  0  0  0  0
  2  1  1  0  0  0  0
  5  8  1  0  0  0  0
  1  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033726

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3

> <INCHI_KEY>
MWOOGOJBHIARFG-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.81738516647897

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3-methoxybenzaldehyde

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
1.224511573333333

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.807246236597697

> <JCHEM_PKA_STRONGEST_BASIC>
-4.895506955382694

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
41.0861

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vanillin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fe29ed7a338>

HMDB0012308
     RDKit          3D
Vanillin
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.2700   -0.9415   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9031    0.2379   -0.9871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7213    0.3403   -0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -0.7169   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3592   -0.6118    0.5226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.7283    0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368   -1.5760    1.2647 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201    0.6029    1.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    1.6543    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393    1.5374    0.3381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425    2.6147    0.2447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -0.9236   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7822   -1.0640   -2.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0312   -1.8666   -1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0340   -1.6652   -0.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310   -2.6473    0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480    0.6815    1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9740    2.5791    1.5355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    3.4932    0.7007 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  2  0
 10 11  1  0
 10  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  6 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
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PDB for #<Metabolite:0x00007fe29ed7a338>

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    8630.9458627.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8629.6188626.722   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8628.2858627.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8626.9518626.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8626.9518625.181   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8628.2848624.411   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8629.6188625.181   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8625.6208624.413   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8632.2768626.720   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8628.2848622.875   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8629.6158622.106   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    3    7    1                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    2                                                       
CONECT    8    5                                                            
CONECT    9    1                                                            
CONECT   10    6   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007fe29ed7a338>

COMPND    HMDB0012308
HETATM    1  C1  UNL     1      -2.270  -0.941  -1.648  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.903   0.238  -0.987  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.721   0.340  -0.282  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.169  -0.717  -0.188  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.359  -0.612   0.523  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.282  -1.728   0.612  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.337  -1.576   1.265  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.620   0.603   1.138  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.731   1.654   1.042  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.439   1.537   0.338  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.342   2.615   0.245  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.393  -0.924  -1.739  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.782  -1.064  -2.641  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.031  -1.867  -1.051  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.034  -1.665  -0.668  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.031  -2.647   0.117  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.548   0.682   1.691  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.974   2.579   1.535  1.00  0.00           H  
HETATM   19  H8  UNL     1      -1.134   3.493   0.701  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   15
CONECT    5    6    8    8
CONECT    6    7    7   16
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   19
END
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SMILES for #<Metabolite:0x00007fe29ed7a338>

COC1=CC(C=O)=CC=C1O
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INCHI for #<Metabolite:0x00007fe29ed7a338>

InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
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Synonyms
ValueSource
3-Methoxy-4-hydroxybenzaldehydeChEBI
4-Formyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxy-benzaldehydeChEBI
4-Hydroxy-3-methoxybenzaldehydeChEBI
4-Hydroxy-m-anisaldehydeChEBI
Methylprotocatechuic aldehydeChEBI
p-Hydroxy-m-methoxybenzaldehydeChEBI
p-VanillinChEBI
VanilineChEBI
VanillaldehydeChEBI
Vanillic aldehydeChEBI
5-BromovanillinMeSH
5-ChlorovanillinMeSH
Vanillin, sodium saltMeSH
2-Methoxy-4-formylphenolHMDB
4-Hydroxy 3-methoxybenzaldehydeHMDB
4-Hydroxy-3-methoxy-benzaldehyde-5-chlorovanillinHMDB
4-Hydroxy-3-methoxybenzaldehyde (acd/name 4.0)HMDB
4-Hydroxy-5-methoxybenzaldehydeHMDB
LioxinHMDB
m-Methoxy-p-hydroxybenzaldehydeHMDB
Methyl-protocatechualdehydeHMDB
Methylprotcatechuic aldehydeHMDB
oleo-Resins vanillaHMDB
oleo-Resins vanilla-beanHMDB
Oleoresin vanillaHMDB
PropenylguaetholHMDB
Protocatechualdehyde 3-methyl etherHMDB
trans-2-Ethoxy-5-(1-propenyl)phenolHMDB
VanilinHMDB
VanillaHMDB
Vanilla oleoresinHMDB
Vanillin (3-methoxy-4-hydroxy- benzaldehyde)HMDB
Vanillin (natural)HMDB
Vanillin (NF)HMDB
Vanillin sodium saltHMDB
VanillineHMDB
ZimcoHMDB
4-Hydroxy-3-methoxy-benzyldehydePhytoBank
VanillumPhytoBank
VanillinHMDB
Molecular FormulaC8H8O3
Average Mass152.1473
Monoisotopic Mass152.047344122
IUPAC Name4-hydroxy-3-methoxybenzaldehyde
Traditional Namevanillin
CAS Registry Number121-33-5
SMILES
COC1=CC(C=O)=CC=C1O
InChI Identifier
InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3
InChI KeyMWOOGOJBHIARFG-UHFFFAOYSA-N