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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:39:24 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034751

Secondary Accession Numbers

HMDB34751

Metabolite Identification

Common Name

Ligustroside

Description

Ligustroside belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Based on a literature review a small amount of articles have been published on Ligustroside.

Structure

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


  Mrv0541 11261207052D          

 38 40  0  0  0  0            999 V2000
   -6.2898    7.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0043    6.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0043    5.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2898    5.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753    5.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753    6.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8608    7.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1464    6.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319    7.1779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0030    7.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885    6.7654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5740    7.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2885    5.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5740    1.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 14 24  1  1  0  0  0
 17 36  1  0  0  0  0
 23 37  2  0  0  0  0
 11 38  1  1  0  0  0
M  END

HMDB0034751
     RDKit          3D
Ligustroside
 69 71  0  0  0  0  0  0  0  0999 V2000
   -0.7076   -1.2437   -2.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 11261207052D          

 38 40  0  0  0  0            999 V2000
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 28 32  1  1  0  0  0
 27 33  1  6  0  0  0
 26 34  1  1  0  0  0
 34 35  1  0  0  0  0
 14 24  1  1  0  0  0
 17 36  1  0  0  0  0
 23 37  2  0  0  0  0
 11 38  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0034751

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(CC(=O)OCCC2=CC=C(O)C=C2)\C(=C\C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3-/t16-,18+,20+,21-,22+,24-,25-/m0/s1

> <INCHI_KEY>
GMQXOLRKJQWPNB-FAWHCFPASA-N

> <FORMULA>
C25H32O12

> <MOLECULAR_WEIGHT>
524.5144

> <EXACT_MASS>
524.189376488

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
52.48290650790564

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S,3Z,4S)-3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.41484107733333386

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.502892958900583

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.94030926159283

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849052288235

> <JCHEM_POLAR_SURFACE_AREA>
181.44

> <JCHEM_REFRACTIVITY>
126.23729999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ligstroside

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034751
     RDKit          3D
Ligustroside
 69 71  0  0  0  0  0  0  0  0999 V2000
   -0.7076   -1.2437   -2.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010    0.0104   -2.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6287    1.0441   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613    1.0565   -1.3988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7190   -0.1233   -1.3849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345   -0.4382   -0.1806 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6453   -1.5492    0.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -1.5960    1.6861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0198   -2.4720    2.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0222   -3.7753    2.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3732   -2.0982    1.8245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7309   -1.9397    3.1790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3079   -1.2397    1.0176 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5416   -1.8648    0.8100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7642   -0.8635   -0.3396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5817    0.1070   -0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    2.0397   -2.2846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019    3.2735   -2.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529    3.4945   -1.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1849    4.8595   -1.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999    5.8157   -2.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1200    5.1071   -1.5772 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133    6.3892   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802    2.3437   -1.4844 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4801    2.4572   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    1.3616    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8992    0.2542    0.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    1.5272    0.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6741    0.5236    0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5811   -0.7079   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5789   -1.6983    0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8657   -1.7040   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8290   -2.6008    0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5251   -3.5503    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4971   -4.4560    1.6499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   -3.5511    1.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -2.6519    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256   -1.1336   -3.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8236   -1.8935   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180   -1.8426   -3.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642    0.1619   -2.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    1.5518   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705    0.3668    0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9544   -0.5493    2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -2.4348    3.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -1.9844    2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8461   -4.2077    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4790   -3.1592    1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9340   -0.9538    3.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5427   -0.2740    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2740   -1.2060    0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -1.7212   -1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4105    0.2712   -0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466    4.1872   -2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683    6.3888   -2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0286    7.1495   -2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    6.7022   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0229    2.3991   -2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    2.4403    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045    3.4051    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7164    0.9244    0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    0.1751    1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8295   -0.4557   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814   -1.1701   -0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0829   -0.9400   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8347   -2.5644   -0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0984   -4.2263    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0094   -4.2947    2.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -2.6531    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 24  3  1  0
 37 31  1  0
 15  6  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  4 42  1  1
  6 43  1  1
  8 44  1  1
  9 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  6
 12 49  1  0
 13 50  1  1
 14 51  1  0
 15 52  1  6
 16 53  1  0
 18 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  6
 25 59  1  0
 25 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 32 65  1  0
 33 66  1  0
 35 67  1  0
 36 68  1  0
 37 69  1  0
M  END

HEADER    PROTEIN                                 26-NOV-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-NOV-12         0                                  
HETATM    1  C   UNK     0     -11.741  13.399   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.075  12.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.075  11.089   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.741  10.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.407  11.089   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.407  12.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.073  13.399   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.740  12.629   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.406  13.399   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.739  13.399   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.405  12.629   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.071  13.399   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.405  11.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.071  10.319   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.262  11.089   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.262  12.629   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.739  10.319   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.071  14.939   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.262  15.709   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.405  15.709   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.262  17.249   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -14.408  10.319   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.072  12.629   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.071   8.779   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.071   6.111   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.301   4.778   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.239   4.778   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.009   6.111   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.239   7.445   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.301   7.445   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.009   8.779   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.549   6.111   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.009   3.444   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.071   3.444   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.301   2.110   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -3.739   8.779   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -5.072  11.089   0.000  0.00  0.00           O+0
HETATM   38  H   UNK     0      -2.405  14.169   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   23                                                       
CONECT   10   23   11                                                       
CONECT   11   12   13   10   38                                             
CONECT   12   11   16   18                                                  
CONECT   13   11   14   17                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   13   36                                                       
CONECT   18   12   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18                                                            
CONECT   21   19                                                            
CONECT   22    3                                                            
CONECT   23    9   10   37                                                  
CONECT   24   30   14                                                       
CONECT   25   26   30                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28   33                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   24   29   25                                                  
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33   27                                                            
CONECT   34   26   35                                                       
CONECT   35   34                                                            
CONECT   36   17                                                            
CONECT   37   23                                                            
CONECT   38   11                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

COMPND    HMDB0034751
HETATM    1  C1  UNL     1      -0.708  -1.244  -2.554  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.001   0.010  -2.279  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.629   1.044  -1.755  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.061   1.056  -1.399  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.719  -0.123  -1.385  1.00  0.00           O  
HETATM    6  C5  UNL     1      -3.335  -0.438  -0.181  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.645  -1.549   0.332  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.962  -1.596   1.686  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.020  -2.472   2.481  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.022  -3.775   2.043  1.00  0.00           O  
HETATM   11  C8  UNL     1      -4.373  -2.098   1.824  1.00  0.00           C  
HETATM   12  O4  UNL     1      -4.731  -1.940   3.179  1.00  0.00           O  
HETATM   13  C9  UNL     1      -5.308  -1.240   1.018  1.00  0.00           C  
HETATM   14  O5  UNL     1      -6.542  -1.865   0.810  1.00  0.00           O  
HETATM   15  C10 UNL     1      -4.764  -0.863  -0.340  1.00  0.00           C  
HETATM   16  O6  UNL     1      -5.582   0.107  -0.863  1.00  0.00           O  
HETATM   17  O7  UNL     1      -2.636   2.040  -2.285  1.00  0.00           O  
HETATM   18  C11 UNL     1      -2.002   3.273  -2.275  1.00  0.00           C  
HETATM   19  C12 UNL     1      -0.753   3.495  -1.918  1.00  0.00           C  
HETATM   20  C13 UNL     1      -0.185   4.860  -1.949  1.00  0.00           C  
HETATM   21  O8  UNL     1      -0.900   5.816  -2.320  1.00  0.00           O  
HETATM   22  O9  UNL     1       1.120   5.107  -1.577  1.00  0.00           O  
HETATM   23  C14 UNL     1       1.713   6.389  -1.587  1.00  0.00           C  
HETATM   24  C15 UNL     1       0.080   2.344  -1.484  1.00  0.00           C  
HETATM   25  C16 UNL     1       0.480   2.457  -0.038  1.00  0.00           C  
HETATM   26  C17 UNL     1       1.394   1.362   0.367  1.00  0.00           C  
HETATM   27  O10 UNL     1       0.899   0.254   0.688  1.00  0.00           O  
HETATM   28  O11 UNL     1       2.768   1.527   0.400  1.00  0.00           O  
HETATM   29  C18 UNL     1       3.674   0.524   0.776  1.00  0.00           C  
HETATM   30  C19 UNL     1       3.581  -0.708  -0.118  1.00  0.00           C  
HETATM   31  C20 UNL     1       4.579  -1.698   0.363  1.00  0.00           C  
HETATM   32  C21 UNL     1       5.866  -1.704  -0.139  1.00  0.00           C  
HETATM   33  C22 UNL     1       6.829  -2.601   0.273  1.00  0.00           C  
HETATM   34  C23 UNL     1       6.525  -3.550   1.232  1.00  0.00           C  
HETATM   35  O12 UNL     1       7.497  -4.456   1.650  1.00  0.00           O  
HETATM   36  C24 UNL     1       5.245  -3.551   1.738  1.00  0.00           C  
HETATM   37  C25 UNL     1       4.281  -2.652   1.324  1.00  0.00           C  
HETATM   38  H1  UNL     1      -1.626  -1.134  -3.167  1.00  0.00           H  
HETATM   39  H2  UNL     1      -0.824  -1.894  -1.668  1.00  0.00           H  
HETATM   40  H3  UNL     1      -0.018  -1.843  -3.228  1.00  0.00           H  
HETATM   41  H4  UNL     1       1.064   0.162  -2.485  1.00  0.00           H  
HETATM   42  H5  UNL     1      -2.122   1.552  -0.382  1.00  0.00           H  
HETATM   43  H6  UNL     1      -3.171   0.367   0.557  1.00  0.00           H  
HETATM   44  H7  UNL     1      -2.954  -0.549   2.049  1.00  0.00           H  
HETATM   45  H8  UNL     1      -2.379  -2.435   3.538  1.00  0.00           H  
HETATM   46  H9  UNL     1      -1.021  -1.984   2.432  1.00  0.00           H  
HETATM   47  H10 UNL     1      -2.846  -4.208   2.414  1.00  0.00           H  
HETATM   48  H11 UNL     1      -4.479  -3.159   1.534  1.00  0.00           H  
HETATM   49  H12 UNL     1      -4.934  -0.954   3.271  1.00  0.00           H  
HETATM   50  H13 UNL     1      -5.543  -0.274   1.544  1.00  0.00           H  
HETATM   51  H14 UNL     1      -7.274  -1.206   0.746  1.00  0.00           H  
HETATM   52  H15 UNL     1      -4.768  -1.721  -1.042  1.00  0.00           H  
HETATM   53  H16 UNL     1      -6.410   0.271  -0.359  1.00  0.00           H  
HETATM   54  H17 UNL     1      -2.547   4.187  -2.586  1.00  0.00           H  
HETATM   55  H18 UNL     1       2.668   6.389  -2.179  1.00  0.00           H  
HETATM   56  H19 UNL     1       1.029   7.149  -2.020  1.00  0.00           H  
HETATM   57  H20 UNL     1       1.890   6.702  -0.531  1.00  0.00           H  
HETATM   58  H21 UNL     1       1.023   2.399  -2.078  1.00  0.00           H  
HETATM   59  H22 UNL     1      -0.398   2.440   0.646  1.00  0.00           H  
HETATM   60  H23 UNL     1       1.004   3.405   0.152  1.00  0.00           H  
HETATM   61  H24 UNL     1       4.716   0.924   0.612  1.00  0.00           H  
HETATM   62  H25 UNL     1       3.560   0.175   1.819  1.00  0.00           H  
HETATM   63  H26 UNL     1       3.830  -0.456  -1.173  1.00  0.00           H  
HETATM   64  H27 UNL     1       2.581  -1.170  -0.090  1.00  0.00           H  
HETATM   65  H28 UNL     1       6.083  -0.940  -0.902  1.00  0.00           H  
HETATM   66  H29 UNL     1       7.835  -2.564  -0.155  1.00  0.00           H  
HETATM   67  H30 UNL     1       8.098  -4.226   2.433  1.00  0.00           H  
HETATM   68  H31 UNL     1       5.009  -4.295   2.488  1.00  0.00           H  
HETATM   69  H32 UNL     1       3.267  -2.653   1.725  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3    3   41
CONECT    3    4   24
CONECT    4    5   17   42
CONECT    5    6
CONECT    6    7   15   43
CONECT    7    8
CONECT    8    9   11   44
CONECT    9   10   45   46
CONECT   10   47
CONECT   11   12   13   48
CONECT   12   49
CONECT   13   14   15   50
CONECT   14   51
CONECT   15   16   52
CONECT   16   53
CONECT   17   18
CONECT   18   19   19   54
CONECT   19   20   24
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   55   56   57
CONECT   24   25   58
CONECT   25   26   59   60
CONECT   26   27   27   28
CONECT   28   29
CONECT   29   30   61   62
CONECT   30   31   63   64
CONECT   31   32   32   37
CONECT   32   33   65
CONECT   33   34   34   66
CONECT   34   35   36
CONECT   35   67
CONECT   36   37   37   68
CONECT   37   69
END

HMDB0034751
     RDKit          3D
Ligustroside
 69 71  0  0  0  0  0  0  0  0999 V2000
   -0.7076   -1.2437   -2.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0010    0.0104   -2.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6287    1.0441   -1.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0613    1.0565   -1.3988 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7190   -0.1233   -1.3849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345   -0.4382   -0.1806 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6453   -1.5492    0.3324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -1.5960    1.6861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0198   -2.4720    2.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0222   -3.7753    2.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3732   -2.0982    1.8245 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7309   -1.9397    3.1790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3079   -1.2397    1.0176 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5416   -1.8648    0.8100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7642   -0.8635   -0.3396 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5817    0.1070   -0.8627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6361    2.0397   -2.2846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019    3.2735   -2.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529    3.4945   -1.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1849    4.8595   -1.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999    5.8157   -2.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1200    5.1071   -1.5772 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7133    6.3892   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802    2.3437   -1.4844 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4801    2.4572   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943    1.3616    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8992    0.2542    0.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    1.5272    0.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6741    0.5236    0.7759 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5811   -0.7079   -0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5789   -1.6983    0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8657   -1.7040   -0.1394 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8290   -2.6008    0.2733 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5251   -3.5503    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4971   -4.4560    1.6499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2454   -3.5511    1.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -2.6519    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6256   -1.1336   -3.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8236   -1.8935   -1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0180   -1.8426   -3.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642    0.1619   -2.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    1.5518   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1705    0.3668    0.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9544   -0.5493    2.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3793   -2.4348    3.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206   -1.9844    2.4319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8461   -4.2077    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4790   -3.1592    1.5339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9340   -0.9538    3.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5427   -0.2740    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2740   -1.2060    0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7685   -1.7212   -1.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4105    0.2712   -0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466    4.1872   -2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6683    6.3888   -2.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0286    7.1495   -2.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8902    6.7022   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0229    2.3991   -2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    2.4403    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045    3.4051    0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7164    0.9244    0.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    0.1751    1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8295   -0.4557   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814   -1.1701   -0.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0829   -0.9400   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8347   -2.5644   -0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0984   -4.2263    2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0094   -4.2947    2.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668   -2.6531    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34 36  1  0
 36 37  2  0
 24  3  1  0
 37 31  1  0
 15  6  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  0
  4 42  1  1
  6 43  1  1
  8 44  1  1
  9 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  6
 12 49  1  0
 13 50  1  1
 14 51  1  0
 15 52  1  6
 16 53  1  0
 18 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  6
 25 59  1  0
 25 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 32 65  1  0
 33 66  1  0
 35 67  1  0
 36 68  1  0
 37 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ligstroside	HMDB
Methyl (2S,4S)-3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator
Ligustroside	MeSH

Chemical Formula

C₂₅H₃₂O₁₂

Average Molecular Weight

524.5144

Monoisotopic Molecular Weight

524.189376488

IUPAC Name

methyl (2S,3Z,4S)-3-ethylidene-4-{2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl}-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

ligstroside

CAS Registry Number

35897-92-8

SMILES

[H][C@]1(CC(=O)OCCC2=CC=C(O)C=C2)\C(=C\C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC

InChI Identifier

InChI=1S/C25H32O12/c1-3-15-16(10-19(28)34-9-8-13-4-6-14(27)7-5-13)17(23(32)33-2)12-35-24(15)37-25-22(31)21(30)20(29)18(11-26)36-25/h3-7,12,16,18,20-22,24-27,29-31H,8-11H2,1-2H3/b15-3-/t16-,18+,20+,21-,22+,24-,25-/m0/s1

InChI Key

GMQXOLRKJQWPNB-FAWHCFPASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Tyrosol derivative
1-hydroxy-2-unsubstituted benzenoid
Phenol
Sugar acid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Benzenoid
Methyl ester
Enoate ester
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Organic oxide
Carbonyl group
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034751)

Cellular substructure

Extracellular (HMDB: HMDB0034751)
Cytoplasm (HMDB: HMDB0034751)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034751)

Source

Endogenous

Endogenous (HMDB: HMDB0034751)

Plant

Plant (HMDB: HMDB0034751)

Animal

Animal (HMDB: HMDB0034751)

Exogenous

Food

Food (HMDB: HMDB0034751)

Vegetable

Root vegetable

Rape (FooDB: FOOD00029)

Fruit vegetable

Olive (FooDB: FOOD00121)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034751)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034751)

Cellular process

Cell signaling (HMDB: HMDB0034751)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034751)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034751)

Nutrient

Nutrient (HMDB: HMDB0034751)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	856 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	0.72 g/L	ALOGPS
logP	0.77	ALOGPS
logP	0.41	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	126.24 m³·mol⁻¹	ChemAxon
Polarizability	52.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	220.103	30932474
DeepCCS	[M-H]-	218.207	30932474
DeepCCS	[M-2H]-	251.72	30932474
DeepCCS	[M+Na]+	225.718	30932474
AllCCS	[M+H]+	220.8	32859911
AllCCS	[M+H-H2O]+	219.2	32859911
AllCCS	[M+NH4]+	222.2	32859911
AllCCS	[M+Na]+	222.6	32859911
AllCCS	[M-H]-	210.3	32859911
AllCCS	[M+Na-2H]-	212.0	32859911
AllCCS	[M+HCOO]-	213.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ligustroside	[H][C@]1(CC(=O)OCCC2=CC=C(O)C=C2)\C(=C\C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC	4722.3	Standard polar	33892256
Ligustroside	[H][C@]1(CC(=O)OCCC2=CC=C(O)C=C2)\C(=C\C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC	3819.8	Standard non polar	33892256
Ligustroside	[H][C@]1(CC(=O)OCCC2=CC=C(O)C=C2)\C(=C\C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC	4136.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ligustroside,1TMS,isomer #1	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3863.0	Semi standard non polar	33892256
Ligustroside,1TMS,isomer #2	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3825.9	Semi standard non polar	33892256
Ligustroside,1TMS,isomer #3	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3831.5	Semi standard non polar	33892256
Ligustroside,1TMS,isomer #4	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3827.6	Semi standard non polar	33892256
Ligustroside,1TMS,isomer #5	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3829.3	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #1	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3804.4	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #10	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3776.4	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #2	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3814.5	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #3	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3816.3	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #4	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3817.5	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #5	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3795.2	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #6	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3780.6	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #7	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3769.6	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #8	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3782.8	Semi standard non polar	33892256
Ligustroside,2TMS,isomer #9	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3770.6	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #1	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3777.2	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #10	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3742.4	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #2	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3780.5	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #3	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3768.7	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #4	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3791.6	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #5	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3776.0	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #6	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3790.6	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #7	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3762.4	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #8	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3738.6	Semi standard non polar	33892256
Ligustroside,3TMS,isomer #9	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3735.6	Semi standard non polar	33892256
Ligustroside,4TMS,isomer #1	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3764.7	Semi standard non polar	33892256
Ligustroside,4TMS,isomer #2	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3749.4	Semi standard non polar	33892256
Ligustroside,4TMS,isomer #3	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3750.2	Semi standard non polar	33892256
Ligustroside,4TMS,isomer #4	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3762.1	Semi standard non polar	33892256
Ligustroside,4TMS,isomer #5	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	3707.5	Semi standard non polar	33892256
Ligustroside,5TMS,isomer #1	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C)C=C1	3728.2	Semi standard non polar	33892256
Ligustroside,1TBDMS,isomer #1	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4094.2	Semi standard non polar	33892256
Ligustroside,1TBDMS,isomer #2	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4048.0	Semi standard non polar	33892256
Ligustroside,1TBDMS,isomer #3	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4041.3	Semi standard non polar	33892256
Ligustroside,1TBDMS,isomer #4	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4030.8	Semi standard non polar	33892256
Ligustroside,1TBDMS,isomer #5	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4034.7	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #1	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4262.6	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #10	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4186.3	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #2	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4256.2	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #3	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4248.3	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #4	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4259.6	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #5	C/C=C1\[C@H](O[C@@H]2O[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]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4214.0	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #6	C/C=C1\[C@H](O[C@@H]2O[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]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4195.1	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #7	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4203.2	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #8	C/C=C1\[C@H](O[C@@H]2O[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]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4184.2	Semi standard non polar	33892256
Ligustroside,2TBDMS,isomer #9	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4177.3	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #1	C/C=C1\[C@H](O[C@@H]2O[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]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4412.1	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #10	C/C=C1\[C@H](O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4304.3	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #2	C/C=C1\[C@H](O[C@@H]2O[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]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4402.5	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #3	C/C=C1\[C@H](O[C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4415.1	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #4	C/C=C1\[C@H](O[C@@H]2O[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]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4395.1	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #5	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4390.8	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #6	C/C=C1\[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	4399.7	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #7	C/C=C1\[C@H](O[C@@H]2O[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]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4337.5	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #8	C/C=C1\[C@H](O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4328.9	Semi standard non polar	33892256
Ligustroside,3TBDMS,isomer #9	C/C=C1\[C@H](O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)OC=C(C(=O)OC)[C@H]1CC(=O)OCCC1=CC=C(O)C=C1	4325.2	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 - Ligustroside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-9807820000-f5c2ec35cb8d0ba79054	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ligustroside GC-MS (2 TMS) - 70eV, Positive	splash10-0udl-4920706000-ea2ce40b8fe272ce689e	2017-10-06	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 - Ligustroside 10V, Positive-QTOF	splash10-03fr-0957140000-7dd3b932ee1351a235c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 20V, Positive-QTOF	splash10-0229-0924000000-5c9631d4b3e47adee3bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 40V, Positive-QTOF	splash10-05fr-3911000000-e16ee238bf0594457610	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 10V, Negative-QTOF	splash10-022i-1529150000-8c6ec59bfafa46670e32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 20V, Negative-QTOF	splash10-03k9-2739110000-ae768efce6b4b2743e98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 40V, Negative-QTOF	splash10-08i3-8975000000-56ce10608df9014e5907	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 10V, Negative-QTOF	splash10-00di-0336390000-cc4f6766122ee0c72ffb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 20V, Negative-QTOF	splash10-0avi-4928630000-2272e006764d06b206cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 40V, Negative-QTOF	splash10-060r-4951040000-de6f37d62db332f572d9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 10V, Positive-QTOF	splash10-0201-0769050000-1ce2df57d86f73742d68	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 20V, Positive-QTOF	splash10-003s-1902000000-60b0548cac18ffb0dc9c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ligustroside 40V, Positive-QTOF	splash10-0100-3920100000-402b050b26ec5d371630	2021-09-23	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

FDB013297

KNApSAcK ID

C00010785

Chemspider ID

8567505

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10392063

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1845521

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Ligustroside (HMDB0034751)

MOL for HMDB0034751 (Ligustroside)

3D MOL for HMDB0034751 (Ligustroside)

3D SDF for HMDB0034751 (Ligustroside)

3D-SDF for HMDB0034751 (Ligustroside)

PDB for HMDB0034751 (Ligustroside)

3D PDB for HMDB0034751 (Ligustroside)

SMILES for HMDB0034751 (Ligustroside)

INCHI for HMDB0034751 (Ligustroside)

Structure for HMDB0034751 (Ligustroside)

3D Structure for HMDB0034751 (Ligustroside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra