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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:01 UTC

Update Date

2022-03-07 02:53:05 UTC

HMDB ID

HMDB0031721

Secondary Accession Numbers

HMDB31721

Metabolite Identification

Common Name

Leonuriside A

Description

Leonuriside A 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 very few articles have been published on Leonuriside A.

Structure

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

HMDB0031721
     RDKit          3D
Leonuriside A
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.2361    0.9239    3.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234    0.9057    2.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642    0.3853    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522   -0.1401    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2211   -0.6653    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4914   -1.1696    0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5623   -0.6558   -0.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -0.1501   -1.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.1332   -2.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2904   -0.6663   -3.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6388    0.3790    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780    0.8938   -0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159    0.1202    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285    0.2376   -1.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438   -0.5426   -1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.0811   -2.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7198    1.2624   -2.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -0.5302    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438   -1.8401    0.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9160   -0.1307    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8170    0.6347    2.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6567    0.6823    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236    1.9946    0.9219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4987    1.3087    4.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    1.5894    3.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257   -0.1193    3.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0181   -0.1227    2.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2681   -0.5050    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0933   -1.0671   -1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7812   -1.6246   -3.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -0.8210   -4.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836    0.0688   -3.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -0.8971    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007   -1.5922   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2835   -0.7058   -2.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580   -0.1079   -3.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5662    1.5796   -1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199    0.1036   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082   -2.3142    0.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.0161    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    1.5655    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    0.6608    2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    2.3026    0.0707 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
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  3  1  0
 22 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
M  END


  Mrv0541 05061306052D          

 23 24  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    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
   -0.7145    2.0625    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
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    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
   -0.7145   -0.4125    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
   -2.1434    2.0625    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20  1  1  0  0  0  0
 20  7  1  0  0  0  0
 21  2  1  0  0  0  0
 21  8  1  0  0  0  0
 22  9  1  0  0  0  0
 22 14  1  0  0  0  0
 23 13  1  0  0  0  0
 23 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031721

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O9/c1-20-7-3-6(16)4-8(21-2)13(7)23-14-12(19)11(18)10(17)9(5-15)22-14/h3-4,9-12,14-19H,5H2,1-2H3

> <INCHI_KEY>
NOQYJICHFNSIFZ-UHFFFAOYSA-N

> <FORMULA>
C14H20O9

> <MOLECULAR_WEIGHT>
332.3032

> <EXACT_MASS>
332.110732238

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
31.76327346147599

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-1.2172954520000003

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20153019304542

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.82313719170174

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923662077906

> <JCHEM_POLAR_SURFACE_AREA>
138.07

> <JCHEM_REFRACTIVITY>
75.09060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031721
     RDKit          3D
Leonuriside A
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.2361    0.9239    3.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234    0.9057    2.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642    0.3853    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522   -0.1401    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2211   -0.6653    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4914   -1.1696    0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5623   -0.6558   -0.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -0.1501   -1.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.1332   -2.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2904   -0.6663   -3.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6388    0.3790    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780    0.8938   -0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159    0.1202    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285    0.2376   -1.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438   -0.5426   -1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.0811   -2.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7198    1.2624   -2.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -0.5302    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438   -1.8401    0.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9160   -0.1307    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8170    0.6347    2.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6567    0.6823    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236    1.9946    0.9219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4987    1.3087    4.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    1.5894    3.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257   -0.1193    3.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0181   -0.1227    2.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2681   -0.5050    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0933   -1.0671   -1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7812   -1.6246   -3.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -0.8210   -4.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836    0.0688   -3.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -0.8971    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007   -1.5922   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2835   -0.7058   -2.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580   -0.1079   -3.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5662    1.5796   -1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199    0.1036   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082   -2.3142    0.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.0161    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    1.5655    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    0.6608    2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    2.3026    0.0707 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
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  3  1  0
 22 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   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  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  -0.770   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      -4.001   3.850   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
HETATM   23  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    6    7                                                       
CONECT    4    6    8                                                       
CONECT    5    9   15                                                       
CONECT    6    3    4   16                                                  
CONECT    7    3   13   20                                                  
CONECT    8    4   13   21                                                  
CONECT    9    5   10   22                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   14   19                                                  
CONECT   13    7    8   23                                                  
CONECT   14   12   22   23                                                  
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20    1    7                                                       
CONECT   21    2    8                                                       
CONECT   22    9   14                                                       
CONECT   23   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0031721
HETATM    1  C1  UNL     1      -2.236   0.924   3.606  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.623   0.906   2.348  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.264   0.385   1.234  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.552  -0.140   1.341  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.221  -0.665   0.259  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.491  -1.170   0.426  1.00  0.00           O  
HETATM    7  C5  UNL     1      -3.562  -0.656  -0.963  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.300  -0.150  -1.108  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.631  -0.133  -2.316  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.290  -0.666  -3.452  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.639   0.379   0.006  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.378   0.894  -0.096  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.816   0.120   0.081  1.00  0.00           C  
HETATM   14  O5  UNL     1       1.528   0.238  -1.098  1.00  0.00           O  
HETATM   15  C10 UNL     1       2.644  -0.543  -1.175  1.00  0.00           C  
HETATM   16  C11 UNL     1       3.406  -0.081  -2.414  1.00  0.00           C  
HETATM   17  O6  UNL     1       3.720   1.262  -2.227  1.00  0.00           O  
HETATM   18  C12 UNL     1       3.530  -0.530   0.020  1.00  0.00           C  
HETATM   19  O7  UNL     1       4.044  -1.840   0.171  1.00  0.00           O  
HETATM   20  C13 UNL     1       2.916  -0.131   1.297  1.00  0.00           C  
HETATM   21  O8  UNL     1       3.817   0.635   2.063  1.00  0.00           O  
HETATM   22  C14 UNL     1       1.657   0.682   1.179  1.00  0.00           C  
HETATM   23  O9  UNL     1       2.024   1.995   0.922  1.00  0.00           O  
HETATM   24  H1  UNL     1      -1.499   1.309   4.345  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.100   1.589   3.584  1.00  0.00           H  
HETATM   26  H3  UNL     1      -2.526  -0.119   3.870  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.018  -0.123   2.313  1.00  0.00           H  
HETATM   28  H5  UNL     1      -6.268  -0.505   0.297  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.093  -1.067  -1.796  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.781  -1.625  -3.259  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.576  -0.821  -4.292  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.084   0.069  -3.732  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.489  -0.897   0.303  1.00  0.00           H  
HETATM   34  H11 UNL     1       2.301  -1.592  -1.413  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.284  -0.706  -2.614  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.658  -0.108  -3.246  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.566   1.580  -1.316  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.420   0.104  -0.196  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.408  -2.314   0.735  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.666  -1.016   1.944  1.00  0.00           H  
HETATM   41  H18 UNL     1       3.513   1.566   2.175  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.105   0.661   2.125  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.624   2.303   0.071  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   27
CONECT    5    6    7    7
CONECT    6   28
CONECT    7    8   29
CONECT    8    9   11   11
CONECT    9   10
CONECT   10   30   31   32
CONECT   11   12
CONECT   12   13
CONECT   13   14   22   33
CONECT   14   15
CONECT   15   16   18   34
CONECT   16   17   35   36
CONECT   17   37
CONECT   18   19   20   38
CONECT   19   39
CONECT   20   21   22   40
CONECT   21   41
CONECT   22   23   42
CONECT   23   43
END

HMDB0031721
     RDKit          3D
Leonuriside A
 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.2361    0.9239    3.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6234    0.9057    2.3480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2642    0.3853    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5522   -0.1401    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2211   -0.6653    0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4914   -1.1696    0.4265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5623   -0.6558   -0.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3002   -0.1501   -1.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.1332   -2.3165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2904   -0.6663   -3.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6388    0.3790    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3780    0.8938   -0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8159    0.1202    0.0809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5285    0.2376   -1.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6438   -0.5426   -1.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4057   -0.0811   -2.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7198    1.2624   -2.2271 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -0.5302    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0438   -1.8401    0.1708 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9160   -0.1307    1.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8170    0.6347    2.0626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6567    0.6823    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0236    1.9946    0.9219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4987    1.3087    4.3452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0997    1.5894    3.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5257   -0.1193    3.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0181   -0.1227    2.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2681   -0.5050    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0933   -1.0671   -1.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7812   -1.6246   -3.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762   -0.8210   -4.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0836    0.0688   -3.7317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -0.8971    0.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3007   -1.5922   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2835   -0.7058   -2.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6580   -0.1079   -3.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5662    1.5796   -1.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199    0.1036   -0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082   -2.3142    0.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.0161    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    1.5655    2.1748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048    0.6608    2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6245    2.3026    0.0707 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
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11  3  1  0
 22 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,6-Dimethoxy-p-hydroquinone 1-O-beta-glucopyranoside	HMDB
4-Hydroxy-2,6-dimethoxyphenyl glucoside	HMDB

Chemical Formula

C₁₄H₂₀O₉

Average Molecular Weight

332.3032

Monoisotopic Molecular Weight

332.110732238

IUPAC Name

2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-(4-hydroxy-2,6-dimethoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

121748-12-7

SMILES

COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C14H20O9/c1-20-7-3-6(16)4-8(21-2)13(7)23-14-12(19)11(18)10(17)9(5-15)22-14/h3-4,9-12,14-19H,5H2,1-2H3

InChI Key

NOQYJICHFNSIFZ-UHFFFAOYSA-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
Hexose monosaccharide
O-glycosyl compound
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
4-alkoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Polyol
Hydrocarbon derivative
Alcohol
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031721)
Cytoplasm (HMDB: HMDB0031721)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031721)

Source

Endogenous

Endogenous (HMDB: HMDB0031721)

Plant

Plant (HMDB: HMDB0031721)
Coffea (HMDB: HMDB0031721)

Exogenous

Food

Food (HMDB: HMDB0031721)

Tea

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0031721)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	232 - 234 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	630300 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.1 g/L	ALOGPS
logP	-0.9	ALOGPS
logP	-1.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	9.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	138.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	75.09 m³·mol⁻¹	ChemAxon
Polarizability	31.76 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
DarkChem	[M+H]+	179.625	31661259
DarkChem	[M-H]-	174.914	31661259
DeepCCS	[M+H]+	174.282	30932474
DeepCCS	[M-H]-	171.924	30932474
DeepCCS	[M-2H]-	205.417	30932474
DeepCCS	[M+Na]+	180.644	30932474
AllCCS	[M+H]+	177.3	32859911
AllCCS	[M+H-H2O]+	174.2	32859911
AllCCS	[M+NH4]+	180.2	32859911
AllCCS	[M+Na]+	181.0	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	174.2	32859911
AllCCS	[M+HCOO]-	174.4	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.	2.77 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3122 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.95 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	222.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	958.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	228.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	76.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	281.3 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	287.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	627.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	591.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	80.9 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	852.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	565.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	424.7 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	275.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Leonuriside A	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O	4705.8	Standard polar	33892256
Leonuriside A	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O	2933.5	Standard non polar	33892256
Leonuriside A	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O	2965.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Leonuriside A,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O	2872.8	Semi standard non polar	33892256
Leonuriside A,1TMS,isomer #2	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O	2854.4	Semi standard non polar	33892256
Leonuriside A,1TMS,isomer #3	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O	2842.9	Semi standard non polar	33892256
Leonuriside A,1TMS,isomer #4	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O	2830.7	Semi standard non polar	33892256
Leonuriside A,1TMS,isomer #5	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C	2850.7	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O	2781.1	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #10	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2797.6	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O	2767.4	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O	2785.1	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #4	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C	2775.0	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #5	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O	2813.4	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #6	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O	2797.3	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #7	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C	2811.1	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #8	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2789.7	Semi standard non polar	33892256
Leonuriside A,2TMS,isomer #9	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2783.1	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O	2735.9	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #10	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2791.5	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O	2730.1	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C	2727.7	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #4	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2725.6	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #5	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2725.1	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #6	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2721.9	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #7	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2793.2	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #8	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2818.1	Semi standard non polar	33892256
Leonuriside A,3TMS,isomer #9	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2791.8	Semi standard non polar	33892256
Leonuriside A,4TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2710.3	Semi standard non polar	33892256
Leonuriside A,4TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2727.5	Semi standard non polar	33892256
Leonuriside A,4TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2696.8	Semi standard non polar	33892256
Leonuriside A,4TMS,isomer #4	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2696.8	Semi standard non polar	33892256
Leonuriside A,4TMS,isomer #5	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2823.6	Semi standard non polar	33892256
Leonuriside A,5TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2739.1	Semi standard non polar	33892256
Leonuriside A,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O	3117.7	Semi standard non polar	33892256
Leonuriside A,1TBDMS,isomer #2	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O	3104.9	Semi standard non polar	33892256
Leonuriside A,1TBDMS,isomer #3	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3108.3	Semi standard non polar	33892256
Leonuriside A,1TBDMS,isomer #4	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	3097.5	Semi standard non polar	33892256
Leonuriside A,1TBDMS,isomer #5	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	3116.8	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O	3254.9	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #10	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3279.4	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3300.5	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	3307.3	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #4	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	3292.5	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #5	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3262.2	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #6	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	3254.6	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #7	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	3261.7	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #8	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3272.2	Semi standard non polar	33892256
Leonuriside A,2TBDMS,isomer #9	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3271.2	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3440.4	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #10	COC1=CC(O)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3408.3	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	3442.6	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	3428.3	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #4	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3454.0	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #5	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3457.3	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #6	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3467.1	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #7	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3430.3	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #8	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3463.4	Semi standard non polar	33892256
Leonuriside A,3TBDMS,isomer #9	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3421.2	Semi standard non polar	33892256
Leonuriside A,4TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3627.1	Semi standard non polar	33892256
Leonuriside A,4TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3675.6	Semi standard non polar	33892256
Leonuriside A,4TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3609.6	Semi standard non polar	33892256
Leonuriside A,4TBDMS,isomer #4	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3588.2	Semi standard non polar	33892256
Leonuriside A,4TBDMS,isomer #5	COC1=CC(O)=CC(OC)=C1OC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3645.8	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 - Leonuriside A GC-MS (Non-derivatized) - 70eV, Positive	splash10-074i-9344000000-32d6099835aadc2dccc9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonuriside A GC-MS (5 TMS) - 70eV, Positive	splash10-004i-0011009000-55a92ab3dc1938f0e2d5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonuriside A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Leonuriside A 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 - Leonuriside A 10V, Positive-QTOF	splash10-00e9-0906000000-382d8787777fc63852a3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 20V, Positive-QTOF	splash10-00di-0900000000-7c550dd26ab634779ba3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 40V, Positive-QTOF	splash10-0aba-3900000000-a243e860d7f765d47af4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 10V, Negative-QTOF	splash10-00lr-1719000000-30bbe191ddfa365beaf8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 20V, Negative-QTOF	splash10-0gb9-1901000000-9633925708483c53e99a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 40V, Negative-QTOF	splash10-0uy0-3900000000-8c75d43d441fb473463d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 10V, Negative-QTOF	splash10-001i-0009000000-4bbc563c39a9745488ac	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 20V, Negative-QTOF	splash10-02ar-2934000000-c148537fe9986583ff91	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 40V, Negative-QTOF	splash10-0zg0-5900000000-665fe4dfeae05a52cdf6	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 10V, Positive-QTOF	splash10-00di-0900000000-e40ab4ef318be62863e0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 20V, Positive-QTOF	splash10-0081-1912000000-ad111e58134a17c4e9c4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Leonuriside A 40V, Positive-QTOF	splash10-0ads-8970000000-b4495c6a34a889525161	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)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

FDB008384

KNApSAcK ID

C00036467

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14237625

PDB ID

Not Available

ChEBI ID

169679

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827591

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 Leonuriside A (HMDB0031721)

MOL for HMDB0031721 (Leonuriside A)

3D MOL for HMDB0031721 (Leonuriside A)

3D SDF for HMDB0031721 (Leonuriside A)

3D-SDF for HMDB0031721 (Leonuriside A)

PDB for HMDB0031721 (Leonuriside A)

3D PDB for HMDB0031721 (Leonuriside A)

SMILES for HMDB0031721 (Leonuriside A)

INCHI for HMDB0031721 (Leonuriside A)

Structure for HMDB0031721 (Leonuriside A)

3D Structure for HMDB0031721 (Leonuriside A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra