Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:42 UTC

Update Date

2022-03-07 02:53:17 UTC

HMDB ID

HMDB0032245

Secondary Accession Numbers

HMDB32245

Metabolite Identification

Common Name

Divanillin

Description

Divanillin, also known as 5,5'-bivanillin or dehydrodivanillin, belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond. Based on a literature review very few articles have been published on Divanillin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0032245
     RDKit          3D
Divanillin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -4.9099    0.3008   -2.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657    0.7212   -1.5882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837    0.0278   -1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856   -1.0507   -2.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755   -1.7323   -2.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587   -2.8775   -2.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172   -3.4904   -2.8410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712   -1.3151   -1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6586   -0.2203   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3624    0.1325    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    0.2601    1.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016    0.5678    2.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606    0.7124    4.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384    0.9861    5.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013    0.7311    2.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794    0.6058    1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9708    0.7624    0.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1043    1.0633    1.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685    0.2994    0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420    0.1707   -1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463    0.4287   -0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1488    1.5337    0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4235    0.3520   -3.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8289    0.9201   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2178   -0.7517   -2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874   -1.3869   -3.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6728   -3.1859   -3.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5957   -1.8405   -1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850    0.1346    2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    0.5891    4.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    0.9752    3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0263    0.9187    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4901    2.0935    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9347    0.3752    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.2864   -1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    1.9025    0.9528 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
  9 21  2  0
 21 22  1  0
 21  3  1  0
 19 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 22 36  1  0
M  END


  Mrv0541 05061306252D          

 22 23  0  0  0  0            999 V2000
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  3  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  2  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  2  0  0  0  0
 14  6  2  0  0  0  0
 15 11  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17  7  2  0  0  0  0
 18  8  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032245

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C=O)=CC(=C1O)C1=C(O)C(OC)=CC(C=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-13-5-9(7-17)3-11(15(13)19)12-4-10(8-18)6-14(22-2)16(12)20/h3-8,19-20H,1-2H3

> <INCHI_KEY>
NSTQUZVZBUTVPY-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.98864108955582

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.1230026926666667

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.894318824912844

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.044778251057476

> <JCHEM_PKA_STRONGEST_BASIC>
-4.59837195427544

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
81.25039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032245
     RDKit          3D
Divanillin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -4.9099    0.3008   -2.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657    0.7212   -1.5882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837    0.0278   -1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856   -1.0507   -2.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755   -1.7323   -2.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587   -2.8775   -2.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172   -3.4904   -2.8410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712   -1.3151   -1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6586   -0.2203   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3624    0.1325    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    0.2601    1.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016    0.5678    2.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606    0.7124    4.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384    0.9861    5.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013    0.7311    2.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794    0.6058    1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9708    0.7624    0.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1043    1.0633    1.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685    0.2994    0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420    0.1707   -1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463    0.4287   -0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1488    1.5337    0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4235    0.3520   -3.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8289    0.9201   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2178   -0.7517   -2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874   -1.3869   -3.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6728   -3.1859   -3.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5957   -1.8405   -1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850    0.1346    2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    0.5891    4.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    0.9752    3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0263    0.9187    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4901    2.0935    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9347    0.3752    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.2864   -1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    1.9025    0.9528 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
  9 21  2  0
 21 22  1  0
 21  3  1  0
 19 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    9   11                                                       
CONECT    4   10   12                                                       
CONECT    5    9   13                                                       
CONECT    6   10   14                                                       
CONECT    7    9   17                                                       
CONECT    8   10   18                                                       
CONECT    9    3    5    7                                                  
CONECT   10    4    6    8                                                  
CONECT   11    3   12   15                                                  
CONECT   12    4   11   16                                                  
CONECT   13    5   15   21                                                  
CONECT   14    6   16   22                                                  
CONECT   15   11   13   19                                                  
CONECT   16   12   14   20                                                  
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    1   13                                                       
CONECT   22    2   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0032245
HETATM    1  C1  UNL     1      -4.910   0.301  -2.559  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.966   0.721  -1.588  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.784   0.028  -1.478  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.486  -1.051  -2.266  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.276  -1.732  -2.128  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.959  -2.877  -2.970  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.117  -3.490  -2.841  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.371  -1.315  -1.188  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.659  -0.220  -0.379  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.362   0.133   0.621  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.004   0.260   1.933  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.002   0.568   2.864  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.661   0.712   4.274  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.538   0.986   5.109  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.301   0.731   2.439  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.679   0.606   1.123  1.00  0.00           C  
HETATM   17  O4  UNL     1       3.971   0.762   0.667  1.00  0.00           O  
HETATM   18  C14 UNL     1       5.104   1.063   1.403  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.669   0.299   0.214  1.00  0.00           C  
HETATM   20  O5  UNL     1       2.042   0.171  -1.120  1.00  0.00           O  
HETATM   21  C16 UNL     1      -1.846   0.429  -0.534  1.00  0.00           C  
HETATM   22  O6  UNL     1      -2.149   1.534   0.270  1.00  0.00           O  
HETATM   23  H1  UNL     1      -4.423   0.352  -3.568  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.829   0.920  -2.549  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.218  -0.752  -2.406  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.187  -1.387  -3.006  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.673  -3.186  -3.709  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.596  -1.841  -1.058  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.985   0.135   2.346  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.343   0.589   4.636  1.00  0.00           H  
HETATM   31  H9  UNL     1       3.111   0.975   3.146  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.026   0.919   2.490  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.490   2.094   1.230  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.935   0.375   1.062  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.974   0.286  -1.433  1.00  0.00           H  
HETATM   36  H14 UNL     1      -1.520   1.903   0.953  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6    8    8
CONECT    6    7    7   27
CONECT    8    9   28
CONECT    9   10   21   21
CONECT   10   11   11   19
CONECT   11   12   29
CONECT   12   13   15   15
CONECT   13   14   14   30
CONECT   15   16   31
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   32   33   34
CONECT   19   20
CONECT   20   35
CONECT   21   22
CONECT   22   36
END

HMDB0032245
     RDKit          3D
Divanillin
 36 37  0  0  0  0  0  0  0  0999 V2000
   -4.9099    0.3008   -2.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657    0.7212   -1.5882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7837    0.0278   -1.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856   -1.0507   -2.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755   -1.7323   -2.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587   -2.8775   -2.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1172   -3.4904   -2.8410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712   -1.3151   -1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6586   -0.2203   -0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3624    0.1325    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    0.2601    1.9333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0016    0.5678    2.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6606    0.7124    4.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384    0.9861    5.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3013    0.7311    2.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6794    0.6058    1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9708    0.7624    0.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1043    1.0633    1.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6685    0.2994    0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420    0.1707   -1.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8463    0.4287   -0.5335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1488    1.5337    0.2697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4235    0.3520   -3.5680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8289    0.9201   -2.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2178   -0.7517   -2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874   -1.3869   -3.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6728   -3.1859   -3.7085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5957   -1.8405   -1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850    0.1346    2.3456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3430    0.5891    4.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113    0.9752    3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0263    0.9187    2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4901    2.0935    1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9347    0.3752    1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9739    0.2864   -1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    1.9025    0.9528 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  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
  9 21  2  0
 21 22  1  0
 21  3  1  0
 19 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 15 31  1  0
 18 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
55-Bisvanillin	HMDB
5,5'-Bivanillin	HMDB
6,6'-Dihydroxy-5,5'-dimethoxy-biphenyl-3,3'-dicarbaldehyde	HMDB
Dehydrodivanillin	HMDB

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

302.07903818

IUPAC Name

3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde

Traditional Name

3-(5-formyl-2-hydroxy-3-methoxyphenyl)-4-hydroxy-5-methoxybenzaldehyde

CAS Registry Number

2092-49-1

SMILES

COC1=CC(C=O)=CC(=C1O)C1=C(O)C(OC)=CC(C=O)=C1

InChI Identifier

InChI=1S/C16H14O6/c1-21-13-5-9(7-17)3-11(15(13)19)12-4-10(8-18)6-14(22-2)16(12)20/h3-8,19-20H,1-2H3

InChI Key

NSTQUZVZBUTVPY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Biphenyls and derivatives

Direct Parent

Biphenyls and derivatives

Alternative Parents

Substituents

Biphenyl
Methoxyphenol
Hydroxybenzaldehyde
Anisole
Benzaldehyde
Benzoyl
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
Phenol
Aryl-aldehyde
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Aldehyde
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

biphenyls (CHEBI:86604 )

Ontology

Cellular substructure

Membrane (HMDB: HMDB0032245)
Cell membrane (HMDB: HMDB0032245)

Source

Endogenous

Endogenous (HMDB: HMDB0032245)

Exogenous

Food

Food (HMDB: HMDB0032245)

Exogenous (HMDB: HMDB0032245)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	315.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	486.00 to 487.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	294.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.567 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	2.7	ALOGPS
logP	2.12	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.04	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.25 m³·mol⁻¹	ChemAxon
Polarizability	29.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.88	31661259
DarkChem	[M-H]-	172.122	31661259
DeepCCS	[M+H]+	172.296	30932474
DeepCCS	[M-H]-	169.938	30932474
DeepCCS	[M-2H]-	203.085	30932474
DeepCCS	[M+Na]+	178.389	30932474
AllCCS	[M+H]+	168.6	32859911
AllCCS	[M+H-H2O]+	165.1	32859911
AllCCS	[M+NH4]+	171.8	32859911
AllCCS	[M+Na]+	172.8	32859911
AllCCS	[M-H]-	169.5	32859911
AllCCS	[M+Na-2H]-	169.1	32859911
AllCCS	[M+HCOO]-	168.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.73 minutes	32390414
Predicted by Siyang on May 30, 2022	13.4909 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.18 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1748.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	311.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	138.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	184.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	626.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	702.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	147.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1050.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	438.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1464.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	539.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	476.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	380.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	140.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Divanillin	COC1=CC(C=O)=CC(=C1O)C1=C(O)C(OC)=CC(C=O)=C1	4571.3	Standard polar	33892256
Divanillin	COC1=CC(C=O)=CC(=C1O)C1=C(O)C(OC)=CC(C=O)=C1	2704.9	Standard non polar	33892256
Divanillin	COC1=CC(C=O)=CC(=C1O)C1=C(O)C(OC)=CC(C=O)=C1	2785.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Divanillin,1TMS,isomer #1	COC1=CC(C=O)=CC(C2=CC(C=O)=CC(OC)=C2O[Si](C)(C)C)=C1O	2642.6	Semi standard non polar	33892256
Divanillin,2TMS,isomer #1	COC1=CC(C=O)=CC(C2=CC(C=O)=CC(OC)=C2O[Si](C)(C)C)=C1O[Si](C)(C)C	2630.7	Semi standard non polar	33892256
Divanillin,1TBDMS,isomer #1	COC1=CC(C=O)=CC(C2=CC(C=O)=CC(OC)=C2O[Si](C)(C)C(C)(C)C)=C1O	2862.4	Semi standard non polar	33892256
Divanillin,2TBDMS,isomer #1	COC1=CC(C=O)=CC(C2=CC(C=O)=CC(OC)=C2O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3070.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Divanillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-0193000000-f933ec0826077351450e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Divanillin GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-4004900000-664b45dc8301e05eec30	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Divanillin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 10V, Positive-QTOF	splash10-0udi-0029000000-2dffc642fbf88a9ebaf9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 20V, Positive-QTOF	splash10-0udi-0489000000-cb10ec00b3f7eacb98d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 40V, Positive-QTOF	splash10-056r-1590000000-3e973ba2379937f48484	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 10V, Negative-QTOF	splash10-0udi-0009000000-f33aca81f233e703ecdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 20V, Negative-QTOF	splash10-0udi-0759000000-283df744ad5b582a449b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 40V, Negative-QTOF	splash10-000i-4950000000-171c0191a07e59f1b30e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 10V, Negative-QTOF	splash10-0udi-0009000000-249366f987125f746469	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 20V, Negative-QTOF	splash10-0a4i-0090000000-5c9e12708f3a8f9cbe03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 40V, Negative-QTOF	splash10-014i-1490000000-316cbd339bd0fed1bf66	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 10V, Positive-QTOF	splash10-002b-0091000000-e3fd70238ba4a64f23ea	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 20V, Positive-QTOF	splash10-004j-0091000000-4b983aa0137c30e4a544	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Divanillin 40V, Positive-QTOF	splash10-0a4l-0791000000-7d9e033dceb9f331aadd	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009334

KNApSAcK ID

Not Available

Chemspider ID

85801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95086

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1407621

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for Divanillin (HMDB0032245)

MOL for HMDB0032245 (Divanillin)

3D MOL for HMDB0032245 (Divanillin)

3D SDF for HMDB0032245 (Divanillin)

3D-SDF for HMDB0032245 (Divanillin)

PDB for HMDB0032245 (Divanillin)

3D PDB for HMDB0032245 (Divanillin)

SMILES for HMDB0032245 (Divanillin)

INCHI for HMDB0032245 (Divanillin)

Structure for HMDB0032245 (Divanillin)

3D Structure for HMDB0032245 (Divanillin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra