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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:13 UTC

Update Date

2022-03-07 02:53:12 UTC

HMDB ID

HMDB0032013

Secondary Accession Numbers

HMDB32013

Metabolite Identification

Common Name

Vanilloloside

Description

Vanilloloside belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review a significant number of articles have been published on Vanilloloside.

Structure

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

HMDB0032013
     RDKit          3D
Vanilloloside
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.1262   -3.1745    0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771   -2.2686    0.5062 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3672   -0.9491    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6733   -0.5251    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312    0.7936   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3599    1.2181   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8855    1.0535   -1.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185    1.6615   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867    1.2186   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2968   -0.0782   -0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346   -0.5761    0.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1615    0.0852   -0.2001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9521    0.1250    0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148    0.7831    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7369    1.5188    1.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0735    0.7039    2.8509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.1827   -0.0247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9863    0.5664   -0.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2582   -1.1002   -0.9029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0199   -2.3496   -0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339   -0.5426   -1.3434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1137    0.3538   -2.3975 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6736   -2.8875    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -3.1147   -0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7438   -4.2160    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4747   -1.2203    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9568    0.6195    0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4486    2.2693    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9518    1.9192   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    2.7016   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967    1.9404   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    1.1466   -0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8371    1.5779   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.0364    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    2.3307    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.2852    3.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5751   -0.7780    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5218    0.8310   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8533   -1.2983   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342   -2.2571    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -1.3910   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.1706   -3.1522 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
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10  3  1  0
 21 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  6
 14 33  1  6
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  1
 18 38  1  0
 19 39  1  6
 20 40  1  0
 21 41  1  6
 22 42  1  0
M  END


  Mrv1652309272007362D          

 22 23  0  0  0  0            999 V2000
   -3.6160    1.8071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3304    1.3946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3304    0.5695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6160    0.1571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9015    0.5695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9015    1.3946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1871    0.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6160    2.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0450    0.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6160   -0.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304    3.0446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0450    1.8071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726    0.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582    0.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0436    0.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0434    1.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7580    1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726    1.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6709    1.8069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3853    1.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7582   -0.6681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437   -1.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  5  6  1  0  0  0  0
  1  8  1  1  0  0  0
  5  7  1  1  0  0  0
  2 12  1  6  0  0  0
  3  9  1  1  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
  7 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 14  2  0  0  0  0
 18 13  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032013

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=CC(CO)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O8/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-4,10-19H,5-6H2,1H3/t10-,11-,12+,13-,14-/m1/s1

> <INCHI_KEY>
SIMPNXWTAVEOTO-RKQHYHRCSA-N

> <FORMULA>
C14H20O8

> <MOLECULAR_WEIGHT>
316.306

> <EXACT_MASS>
316.115817604

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.085661252190707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxane-3,4,5-triol

> <ALOGPS_LOGP>
-1.00

> <JCHEM_LOGP>
-1.5234086319999993

> <ALOGPS_LOGS>
-1.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.189064304159064

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199222468921356

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8257256418131345

> <JCHEM_POLAR_SURFACE_AREA>
128.84

> <JCHEM_REFRACTIVITY>
73.4624

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032013
     RDKit          3D
Vanilloloside
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.1262   -3.1745    0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771   -2.2686    0.5062 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3672   -0.9491    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6733   -0.5251    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312    0.7936   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3599    1.2181   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8855    1.0535   -1.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185    1.6615   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867    1.2186   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2968   -0.0782   -0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346   -0.5761    0.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1615    0.0852   -0.2001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9521    0.1250    0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148    0.7831    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7369    1.5188    1.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0735    0.7039    2.8509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.1827   -0.0247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9863    0.5664   -0.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2582   -1.1002   -0.9029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0199   -2.3496   -0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339   -0.5426   -1.3434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1137    0.3538   -2.3975 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6736   -2.8875    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -3.1147   -0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7438   -4.2160    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4747   -1.2203    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9568    0.6195    0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4486    2.2693    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9518    1.9192   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    2.7016   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967    1.9404   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    1.1466   -0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8371    1.5779   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.0364    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    2.3307    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.2852    3.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5751   -0.7780    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5218    0.8310   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8533   -1.2983   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342   -2.2571    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -1.3910   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.1706   -3.1522 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
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10  3  1  0
 21 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  6
 14 33  1  6
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  1
 18 38  1  0
 19 39  1  6
 20 40  1  0
 21 41  1  6
 22 42  1  0
M  END

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      -6.750   3.373   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.083   2.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.083   1.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.750   0.293   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.416   1.063   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.416   2.603   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -4.083   0.293   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.750   4.913   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.417   0.293   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -6.750  -1.246   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -8.083   5.683   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -9.417   3.373   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.749   1.063   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.415   0.293   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.081   1.063   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.081   2.603   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.415   3.373   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.749   2.603   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.252   3.373   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.586   2.603   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.415  -1.247   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.082  -2.017   0.000  0.00  0.00           C+0
CONECT    1    2    6    8                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5   13                                                       
CONECT    8    1   11                                                       
CONECT    9    3                                                            
CONECT   10    4                                                            
CONECT   11    8                                                            
CONECT   12    2                                                            
CONECT   13    7   14   18                                                  
CONECT   14   15   13   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19   16   20                                                       
CONECT   20   19                                                            
CONECT   21   14   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0032013
HETATM    1  C1  UNL     1       3.126  -3.175   0.769  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.077  -2.269   0.506  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.367  -0.949   0.203  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.673  -0.525   0.160  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.931   0.794  -0.144  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.360   1.218  -0.183  1.00  0.00           C  
HETATM    7  O2  UNL     1       5.886   1.053  -1.467  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.918   1.662  -0.397  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.587   1.219  -0.350  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.297  -0.078  -0.052  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.035  -0.576   0.011  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.162   0.085  -0.200  1.00  0.00           C  
HETATM   13  O4  UNL     1      -1.952   0.125   0.970  1.00  0.00           O  
HETATM   14  C10 UNL     1      -3.115   0.783   0.638  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.737   1.519   1.798  1.00  0.00           C  
HETATM   16  O5  UNL     1      -4.073   0.704   2.851  1.00  0.00           O  
HETATM   17  C12 UNL     1      -4.042  -0.183  -0.025  1.00  0.00           C  
HETATM   18  O6  UNL     1      -4.986   0.566  -0.744  1.00  0.00           O  
HETATM   19  C13 UNL     1      -3.258  -1.100  -0.903  1.00  0.00           C  
HETATM   20  O7  UNL     1      -3.020  -2.350  -0.306  1.00  0.00           O  
HETATM   21  C14 UNL     1      -1.934  -0.543  -1.343  1.00  0.00           C  
HETATM   22  O8  UNL     1      -2.114   0.354  -2.398  1.00  0.00           O  
HETATM   23  H1  UNL     1       3.674  -2.888   1.689  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.849  -3.115  -0.073  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.744  -4.216   0.825  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.475  -1.220   0.361  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.957   0.620   0.539  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.449   2.269   0.104  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.952   1.919  -1.958  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.101   2.702  -0.637  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.797   1.940  -0.557  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.990   1.147  -0.447  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.837   1.578  -0.115  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.646   2.036   1.389  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.037   2.331   2.080  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.224   1.285   3.646  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.575  -0.778   0.741  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.522   0.831  -1.589  1.00  0.00           H  
HETATM   39  H17 UNL     1      -3.853  -1.298  -1.815  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.334  -2.257   0.629  1.00  0.00           H  
HETATM   41  H19 UNL     1      -1.341  -1.391  -1.755  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.501   0.171  -3.152  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   26
CONECT    5    6    8    8
CONECT    6    7   27   28
CONECT    7   29
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11
CONECT   11   12
CONECT   12   13   21   32
CONECT   13   14
CONECT   14   15   17   33
CONECT   15   16   34   35
CONECT   16   36
CONECT   17   18   19   37
CONECT   18   38
CONECT   19   20   21   39
CONECT   20   40
CONECT   21   22   41
CONECT   22   42
END

HMDB0032013
     RDKit          3D
Vanilloloside
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.1262   -3.1745    0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0771   -2.2686    0.5062 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3672   -0.9491    0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6733   -0.5251    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312    0.7936   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3599    1.2181   -0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8855    1.0535   -1.4669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185    1.6615   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5867    1.2186   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2968   -0.0782   -0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0346   -0.5761    0.0110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1615    0.0852   -0.2001 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9521    0.1250    0.9697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1148    0.7831    0.6378 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7369    1.5188    1.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0735    0.7039    2.8509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0425   -0.1827   -0.0247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9863    0.5664   -0.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2582   -1.1002   -0.9029 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0199   -2.3496   -0.3063 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339   -0.5426   -1.3434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1137    0.3538   -2.3975 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6736   -2.8875    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8495   -3.1147   -0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7438   -4.2160    0.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4747   -1.2203    0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9568    0.6195    0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4486    2.2693    0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9518    1.9192   -1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1006    2.7016   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7967    1.9404   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899    1.1466   -0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8371    1.5779   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457    2.0364    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0367    2.3307    2.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239    1.2852    3.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5751   -0.7780    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5218    0.8310   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8533   -1.2983   -1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342   -2.2571    0.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -1.3910   -1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014    0.1706   -3.1522 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
  5  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10  3  1  0
 21 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  6
 14 33  1  6
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  1
 18 38  1  0
 19 39  1  6
 20 40  1  0
 21 41  1  6
 22 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-(Hydroxymethyl)-2-methoxyphenyl beta-D-glucopyranoside	PhytoBank
4-(Hydroxymethyl)-2-methoxyphenyl β-D-glucopyranoside	PhytoBank
Vanillyl alcohol 4-O-beta-D-glucopyranoside	PhytoBank
Vanillyl alcohol 4-O-β-D-glucopyranoside	PhytoBank

Chemical Formula

C₁₄H₂₀O₈

Average Molecular Weight

316.306

Monoisotopic Molecular Weight

316.115817604

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxane-3,4,5-triol

Traditional Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxane-3,4,5-triol

CAS Registry Number

74950-96-2

SMILES

COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=CC(CO)=C1

InChI Identifier

InChI=1S/C14H20O8/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-4,10-19H,5-6H2,1H3/t10-,11-,12+,13-,14-/m1/s1

InChI Key

SIMPNXWTAVEOTO-RKQHYHRCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Phenoxy compound
Anisole
Methoxybenzene
Benzyl alcohol
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Oxacycle
Ether
Organoheterocyclic compound
Acetal
Polyol
Hydrocarbon derivative
Alcohol
Aromatic alcohol
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

glycoside (CHEBI:68967 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032013)
Cytoplasm (HMDB: HMDB0032013)

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	120 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.1 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1.5	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	128.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.46 m³·mol⁻¹	ChemAxon
Polarizability	31.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DeepCCS	[M+H]+	185.742	30932474
DeepCCS	[M-H]-	183.346	30932474
DeepCCS	[M-2H]-	216.741	30932474
DeepCCS	[M+Na]+	191.654	30932474
AllCCS	[M+H]+	174.4	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.3	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	171.3	32859911
AllCCS	[M+Na-2H]-	171.4	32859911
AllCCS	[M+HCOO]-	171.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vanilloloside	COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=CC(CO)=C1	3606.4	Standard polar	33892256
Vanilloloside	COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=CC(CO)=C1	2900.2	Standard non polar	33892256
Vanilloloside	COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=CC(CO)=C1	2822.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vanilloloside,1TMS,isomer #1	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2640.3	Semi standard non polar	33892256
Vanilloloside,1TMS,isomer #2	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2634.0	Semi standard non polar	33892256
Vanilloloside,1TMS,isomer #3	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2638.6	Semi standard non polar	33892256
Vanilloloside,1TMS,isomer #4	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2647.3	Semi standard non polar	33892256
Vanilloloside,1TMS,isomer #5	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	2658.4	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2582.2	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #10	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2601.6	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #2	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2600.3	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #3	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2602.5	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #4	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2599.4	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #5	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2589.8	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #6	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2608.2	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #7	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2611.4	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #8	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2593.3	Semi standard non polar	33892256
Vanilloloside,2TMS,isomer #9	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2606.9	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2548.6	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #10	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2573.2	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #2	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2581.6	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #3	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2560.3	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #4	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2582.2	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #5	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2605.5	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #6	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2587.1	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #7	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2576.5	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #8	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2591.2	Semi standard non polar	33892256
Vanilloloside,3TMS,isomer #9	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2596.7	Semi standard non polar	33892256
Vanilloloside,4TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2588.9	Semi standard non polar	33892256
Vanilloloside,4TMS,isomer #2	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2621.9	Semi standard non polar	33892256
Vanilloloside,4TMS,isomer #3	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2585.2	Semi standard non polar	33892256
Vanilloloside,4TMS,isomer #4	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2629.7	Semi standard non polar	33892256
Vanilloloside,4TMS,isomer #5	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2601.6	Semi standard non polar	33892256
Vanilloloside,5TMS,isomer #1	COC1=CC(CO[Si](C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2640.8	Semi standard non polar	33892256
Vanilloloside,1TBDMS,isomer #1	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2887.2	Semi standard non polar	33892256
Vanilloloside,1TBDMS,isomer #2	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2885.2	Semi standard non polar	33892256
Vanilloloside,1TBDMS,isomer #3	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2887.1	Semi standard non polar	33892256
Vanilloloside,1TBDMS,isomer #4	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2897.6	Semi standard non polar	33892256
Vanilloloside,1TBDMS,isomer #5	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	2893.2	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	3099.1	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #10	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3124.8	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #2	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3108.2	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #3	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3110.8	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #4	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3111.8	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #5	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3115.0	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #6	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3119.6	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #7	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3127.4	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #8	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3120.2	Semi standard non polar	33892256
Vanilloloside,2TBDMS,isomer #9	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3117.7	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3305.0	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #10	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3329.4	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #2	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3310.5	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #3	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3313.6	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #4	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3288.9	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #5	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3326.8	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #6	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3283.7	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #7	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3317.7	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #8	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3328.6	Semi standard non polar	33892256
Vanilloloside,3TBDMS,isomer #9	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3304.3	Semi standard non polar	33892256
Vanilloloside,4TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3482.6	Semi standard non polar	33892256
Vanilloloside,4TBDMS,isomer #2	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3511.8	Semi standard non polar	33892256
Vanilloloside,4TBDMS,isomer #3	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3486.0	Semi standard non polar	33892256
Vanilloloside,4TBDMS,isomer #4	COC1=CC(CO)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3507.3	Semi standard non polar	33892256
Vanilloloside,4TBDMS,isomer #5	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3484.8	Semi standard non polar	33892256
Vanilloloside,5TBDMS,isomer #1	COC1=CC(CO[Si](C)(C)C(C)(C)C)=CC=C1O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3688.2	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 - Vanilloloside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0abj-7490000000-07d362e5ba14ba816a24	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanilloloside 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 - Vanilloloside 10V, Positive-QTOF	splash10-0ap1-0942000000-392ca0b4db0a343bf991	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 20V, Positive-QTOF	splash10-000i-0900000000-3b59a65ccff488eeaddb	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 40V, Positive-QTOF	splash10-000i-2900000000-b9eaf99192ba0f64574e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 10V, Negative-QTOF	splash10-0gb9-0936000000-4a04d18735cfc1b97baf	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 20V, Negative-QTOF	splash10-0udr-1920000000-a81b515fdb147c601a01	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 40V, Negative-QTOF	splash10-0fe0-3900000000-6eec0b42db3a4674e4d4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 10V, Negative-QTOF	splash10-0uy0-0903000000-60c0747052909778a641	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 20V, Negative-QTOF	splash10-05g0-2921000000-5d8f6fd63501bd743d5a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 40V, Negative-QTOF	splash10-0m50-4902000000-c6c30a8b36fd0110fbe5	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 10V, Positive-QTOF	splash10-014j-0789000000-afb48266f5de300f4fd0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 20V, Positive-QTOF	splash10-000i-0910000000-3018083ab01e891395b0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanilloloside 40V, Positive-QTOF	splash10-01wr-3910000000-7d65f52b27cbb5b6ae0e	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB008711

KNApSAcK ID

C00032471

Chemspider ID

24695215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44577222

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Vanilloloside (HMDB0032013)

MOL for HMDB0032013 (Vanilloloside)

3D MOL for HMDB0032013 (Vanilloloside)

3D SDF for HMDB0032013 (Vanilloloside)

3D-SDF for HMDB0032013 (Vanilloloside)

PDB for HMDB0032013 (Vanilloloside)

3D PDB for HMDB0032013 (Vanilloloside)

SMILES for HMDB0032013 (Vanilloloside)

INCHI for HMDB0032013 (Vanilloloside)

Structure for HMDB0032013 (Vanilloloside)

3D Structure for HMDB0032013 (Vanilloloside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra