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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:14 UTC

Update Date

2022-03-07 02:52:42 UTC

HMDB ID

HMDB0030821

Secondary Accession Numbers

HMDB30821

Metabolite Identification

Common Name

Cichoriin

Description

Cichoriin belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Cichoriin is found, on average, in the highest concentration within chicories (Cichorium intybus). Cichoriin has also been detected, but not quantified in, green vegetables. This could make cichoriin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cichoriin.

Structure

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

HMDB0030821
     RDKit          3D
Cichoriin
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.4167   -1.3915    2.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6952   -0.7608    1.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163    0.1304    0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848    0.7950   -0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1132    0.5795   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844    1.2478   -0.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9057    1.0334   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025    1.7202   -1.8777 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    0.1276   -0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558   -0.1745   -0.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832    0.2203   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8781    0.8775    0.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2179    0.6175    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9173    1.4593    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2944    1.2614    1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3974   -0.8340    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715   -1.0073    1.7780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -1.6633   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8043   -2.2369   -1.2150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009   -0.9174   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -0.4489   -2.4361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.5444    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -0.3341    0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4030   -0.9510    1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3902    0.2807    0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882    1.5027   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844    1.9590   -1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    2.3909   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    0.9727   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6651    0.8390   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6373    2.5162    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4558    1.1907    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570    0.8133    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4495   -1.0841    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8518   -1.9337    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2572   -2.5241    0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283   -1.7402   -2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230   -1.6017   -1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    0.4068   -2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881   -1.2517    1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 20 11  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END


  Mrv0541 05061305322D          

 24 26  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  1  0  0  0  0
 11  2  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  5  1  0  0  0  0
 17  7  1  0  0  0  0
 18 11  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  8  1  0  0  0  0
 22 11  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 10  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030821

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(OC2=C(O)C=C3C=CC(=O)OC3=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-4-8-6(3-7(9)17)1-2-11(18)22-8/h1-4,10,12-17,19-21H,5H2

> <INCHI_KEY>
WNBCMONIPIJTSB-UHFFFAOYSA-N

> <FORMULA>
C15H16O9

> <MOLECULAR_WEIGHT>
340.2821

> <EXACT_MASS>
340.07943211

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
31.62181628231513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-1.0918391213333336

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.201394765626482

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.689078631960554

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354940242

> <JCHEM_POLAR_SURFACE_AREA>
145.91

> <JCHEM_REFRACTIVITY>
77.65480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030821
     RDKit          3D
Cichoriin
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.4167   -1.3915    2.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6952   -0.7608    1.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163    0.1304    0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848    0.7950   -0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1132    0.5795   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844    1.2478   -0.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9057    1.0334   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025    1.7202   -1.8777 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    0.1276   -0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558   -0.1745   -0.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832    0.2203   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8781    0.8775    0.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2179    0.6175    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9173    1.4593    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2944    1.2614    1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3974   -0.8340    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715   -1.0073    1.7780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -1.6633   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8043   -2.2369   -1.2150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009   -0.9174   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -0.4489   -2.4361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.5444    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -0.3341    0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4030   -0.9510    1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3902    0.2807    0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882    1.5027   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844    1.9590   -1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    2.3909   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    0.9727   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6651    0.8390   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6373    2.5162    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4558    1.1907    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570    0.8133    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4495   -1.0841    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8518   -1.9337    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2572   -2.5241    0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283   -1.7402   -2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230   -1.6017   -1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    0.4068   -2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881   -1.2517    1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 20 11  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1   11                                                       
CONECT    3    6    7                                                       
CONECT    4    8    9                                                       
CONECT    5   10   16                                                       
CONECT    6    1    3    8                                                  
CONECT    7    3    9   17                                                  
CONECT    8    4    6   22                                                  
CONECT    9    4    7   23                                                  
CONECT   10    5   12   24                                                  
CONECT   11    2   18   22                                                  
CONECT   12   10   13   19                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   23   24                                                  
CONECT   16    5                                                            
CONECT   17    7                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22    8   11                                                       
CONECT   23    9   15                                                       
CONECT   24   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0030821
HETATM    1  O1  UNL     1       6.417  -1.392   2.463  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.695  -0.761   1.648  1.00  0.00           C  
HETATM    3  C2  UNL     1       6.316   0.130   0.797  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.485   0.795  -0.075  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.113   0.580  -0.092  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.284   1.248  -0.967  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.906   1.033  -0.987  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.102   1.720  -1.878  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.378   0.128  -0.103  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.056  -0.174  -0.017  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.083   0.220  -0.653  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.878   0.878   0.284  1.00  0.00           O  
HETATM   13  C9  UNL     1      -3.218   0.618   0.200  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.917   1.459   1.246  1.00  0.00           C  
HETATM   15  O5  UNL     1      -5.294   1.261   1.237  1.00  0.00           O  
HETATM   16  C11 UNL     1      -3.397  -0.834   0.601  1.00  0.00           C  
HETATM   17  O6  UNL     1      -2.672  -1.007   1.778  1.00  0.00           O  
HETATM   18  C12 UNL     1      -2.752  -1.663  -0.461  1.00  0.00           C  
HETATM   19  O7  UNL     1      -3.804  -2.237  -1.215  1.00  0.00           O  
HETATM   20  C13 UNL     1      -1.801  -0.917  -1.332  1.00  0.00           C  
HETATM   21  O8  UNL     1      -2.516  -0.449  -2.436  1.00  0.00           O  
HETATM   22  C14 UNL     1       2.241  -0.544   0.783  1.00  0.00           C  
HETATM   23  C15 UNL     1       3.574  -0.334   0.799  1.00  0.00           C  
HETATM   24  O9  UNL     1       4.403  -0.951   1.618  1.00  0.00           O  
HETATM   25  H1  UNL     1       7.390   0.281   0.830  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.888   1.503  -0.768  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.684   1.959  -1.664  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.446   2.391  -2.541  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.877   0.973  -1.430  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.665   0.839  -0.787  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.637   2.516   1.039  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.456   1.191   2.225  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.557   0.813   2.078  1.00  0.00           H  
HETATM   34  H10 UNL     1      -4.449  -1.084   0.746  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.852  -1.934   2.078  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.257  -2.524   0.033  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.928  -1.740  -2.064  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.023  -1.602  -1.732  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.133   0.407  -2.749  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.788  -1.252   1.466  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   24
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   23
CONECT    6    7   27
CONECT    7    8    9    9
CONECT    8   28
CONECT    9   10   22
CONECT   10   11
CONECT   11   12   20   29
CONECT   12   13
CONECT   13   14   16   30
CONECT   14   15   31   32
CONECT   15   33
CONECT   16   17   18   34
CONECT   17   35
CONECT   18   19   20   36
CONECT   19   37
CONECT   20   21   38
CONECT   21   39
CONECT   22   23   23   40
CONECT   23   24
END

HMDB0030821
     RDKit          3D
Cichoriin
 40 42  0  0  0  0  0  0  0  0999 V2000
    6.4167   -1.3915    2.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6952   -0.7608    1.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3163    0.1304    0.7969 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848    0.7950   -0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1132    0.5795   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2844    1.2478   -0.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9057    1.0334   -0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025    1.7202   -1.8777 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3782    0.1276   -0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558   -0.1745   -0.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0832    0.2203   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8781    0.8775    0.2838 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2179    0.6175    0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9173    1.4593    1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2944    1.2614    1.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3974   -0.8340    0.6008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6715   -1.0073    1.7780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -1.6633   -0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8043   -2.2369   -1.2150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8009   -0.9174   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5160   -0.4489   -2.4361 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -0.5444    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5738   -0.3341    0.7987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4030   -0.9510    1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3902    0.2807    0.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8882    1.5027   -0.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844    1.9590   -1.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459    2.3909   -2.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    0.9727   -1.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6651    0.8390   -0.7875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6373    2.5162    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4558    1.1907    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5570    0.8133    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4495   -1.0841    0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8518   -1.9337    2.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2572   -2.5241    0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283   -1.7402   -2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0230   -1.6017   -1.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331    0.4068   -2.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881   -1.2517    1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
  9 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 20 11  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
6-Hydroxyskimmin	HMDB
Cichorioside	HMDB

Chemical Formula

C₁₅H₁₆O₉

Average Molecular Weight

340.2821

Monoisotopic Molecular Weight

340.07943211

IUPAC Name

6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one

Traditional Name

6-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-2-one

CAS Registry Number

531-58-8

SMILES

OCC1OC(OC2=C(O)C=C3C=CC(=O)OC3=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-4-8-6(3-7(9)17)1-2-11(18)22-8/h1-4,10,12-17,19-21H,5H2

InChI Key

WNBCMONIPIJTSB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin o-glycoside
Coumarin-7-o-glycoside
Phenolic glycoside
Hydroxycoumarin
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Benzenoid
Pyran
Oxane
Heteroaromatic compound
Secondary alcohol
Lactone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	213 - 214 °C	Not Available
Boiling Point	697.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	206000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-2.450 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.8 g/L	ALOGPS
logP	-0.54	ALOGPS
logP	-1.1	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.69	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	145.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.65 m³·mol⁻¹	ChemAxon
Polarizability	31.62 Å³	ChemAxon
Number of Rings	3	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]+	177.75	31661259
DarkChem	[M-H]-	177.096	31661259
DeepCCS	[M+H]+	177.422	30932474
DeepCCS	[M-H]-	175.064	30932474
DeepCCS	[M-2H]-	209.111	30932474
DeepCCS	[M+Na]+	184.338	30932474
AllCCS	[M+H]+	177.4	32859911
AllCCS	[M+H-H2O]+	174.3	32859911
AllCCS	[M+NH4]+	180.3	32859911
AllCCS	[M+Na]+	181.2	32859911
AllCCS	[M-H]-	174.4	32859911
AllCCS	[M+Na-2H]-	174.1	32859911
AllCCS	[M+HCOO]-	173.9	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.	2.71 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9912 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.6 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	184.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1036.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	82.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	53.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	297.2 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	293.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	496.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	599.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	144.2 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	975.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	209.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	554.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	440.3 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	289.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cichoriin	OCC1OC(OC2=C(O)C=C3C=CC(=O)OC3=C2)C(O)C(O)C1O	4326.6	Standard polar	33892256
Cichoriin	OCC1OC(OC2=C(O)C=C3C=CC(=O)OC3=C2)C(O)C(O)C1O	3236.0	Standard non polar	33892256
Cichoriin	OCC1OC(OC2=C(O)C=C3C=CC(=O)OC3=C2)C(O)C(O)C1O	3381.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cichoriin,1TMS,isomer #1	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C(O)C1O	3286.2	Semi standard non polar	33892256
Cichoriin,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O)C(O)C1O)OC(=O)C=C2	3352.6	Semi standard non polar	33892256
Cichoriin,1TMS,isomer #3	C[Si](C)(C)OC1C(OC2=CC3=C(C=CC(=O)O3)C=C2O)OC(CO)C(O)C1O	3297.5	Semi standard non polar	33892256
Cichoriin,1TMS,isomer #4	C[Si](C)(C)OC1C(O)C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C1O	3283.9	Semi standard non polar	33892256
Cichoriin,1TMS,isomer #5	C[Si](C)(C)OC1C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C1O	3296.0	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #1	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C)C(O)C(O)C1O	3207.2	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #10	C[Si](C)(C)OC1C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C1O[Si](C)(C)C	3170.8	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #2	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C)C(O)C1O	3201.7	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #3	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C(O[Si](C)(C)C)C1O	3225.9	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #4	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C(O)C1O[Si](C)(C)C	3199.5	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O)OC(=O)C=C2	3203.2	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #6	C[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O)OC(=O)C=C2	3220.9	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #7	C[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C)OC(=O)C=C2	3194.6	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #8	C[Si](C)(C)OC1C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C)C1O	3180.0	Semi standard non polar	33892256
Cichoriin,2TMS,isomer #9	C[Si](C)(C)OC1C(OC2=CC3=C(C=CC(=O)O3)C=C2O)OC(CO)C(O)C1O[Si](C)(C)C	3186.4	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #1	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O	3123.3	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #10	C[Si](C)(C)OC1C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3130.0	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #2	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O	3151.8	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #3	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C	3133.9	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #4	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	3142.8	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #5	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	3168.8	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #6	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3147.2	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #7	C[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)OC(=O)C=C2	3140.0	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #8	C[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)OC(=O)C=C2	3140.0	Semi standard non polar	33892256
Cichoriin,3TMS,isomer #9	C[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)OC(=O)C=C2	3140.5	Semi standard non polar	33892256
Cichoriin,4TMS,isomer #1	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	3106.4	Semi standard non polar	33892256
Cichoriin,4TMS,isomer #2	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	3136.4	Semi standard non polar	33892256
Cichoriin,4TMS,isomer #3	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3103.3	Semi standard non polar	33892256
Cichoriin,4TMS,isomer #4	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3140.4	Semi standard non polar	33892256
Cichoriin,4TMS,isomer #5	C[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)OC(=O)C=C2	3121.4	Semi standard non polar	33892256
Cichoriin,5TMS,isomer #1	C[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	3147.7	Semi standard non polar	33892256
Cichoriin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C(O)C1O	3563.5	Semi standard non polar	33892256
Cichoriin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O)C(O)C1O)OC(=O)C=C2	3587.4	Semi standard non polar	33892256
Cichoriin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C(OC2=CC3=C(C=CC(=O)O3)C=C2O)OC(CO)C(O)C1O	3581.6	Semi standard non polar	33892256
Cichoriin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C(O)C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C1O	3575.9	Semi standard non polar	33892256
Cichoriin,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C1O	3574.0	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C(C)(C)C)C(O)C(O)C1O	3741.2	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C1O[Si](C)(C)C(C)(C)C	3739.3	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3740.6	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	3765.5	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	3748.9	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)OC(=O)C=C2	3760.8	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)OC(=O)C=C2	3783.9	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)OC(=O)C=C2	3750.8	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C(C)(C)C)C1O	3741.6	Semi standard non polar	33892256
Cichoriin,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1C(OC2=CC3=C(C=CC(=O)O3)C=C2O)OC(CO)C(O)C1O[Si](C)(C)C(C)(C)C	3752.6	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3891.8	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3915.4	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	3933.9	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	3913.0	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3909.7	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3936.6	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3932.0	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O)OC(=O)C=C2	3926.0	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)OC(=O)C=C2	3928.7	Semi standard non polar	33892256
Cichoriin,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1OC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)OC(=O)C=C2	3937.5	Semi standard non polar	33892256
Cichoriin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[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	4057.2	Semi standard non polar	33892256
Cichoriin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[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	4091.4	Semi standard non polar	33892256
Cichoriin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O[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	4067.4	Semi standard non polar	33892256
Cichoriin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC3=C(C=CC(=O)O3)C=C2O)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	4102.7	Semi standard non polar	33892256
Cichoriin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=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)OC(=O)C=C2	4053.9	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 - Cichoriin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6936000000-3189ea8a0aabc709aeeb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cichoriin GC-MS (4 TMS) - 70eV, Positive	splash10-03di-2353029000-f90429c99944a173ba08	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cichoriin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cichoriin 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 - Cichoriin 10V, Positive-QTOF	splash10-004l-0906000000-f762a68df017c1e2cf1b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 20V, Positive-QTOF	splash10-004i-0900000000-fb12040f73f72a76812c	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 40V, Positive-QTOF	splash10-03g0-1900000000-2fbb8c50f201999f6a46	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 10V, Negative-QTOF	splash10-002r-1729000000-89269076594cc9193b20	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 20V, Negative-QTOF	splash10-004i-1911000000-f1a95af0387b6dde5f7c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 40V, Negative-QTOF	splash10-003r-2900000000-d654c6d1bd26299bd5e4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 10V, Positive-QTOF	splash10-002f-0309000000-7684d5d21391172250be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 20V, Positive-QTOF	splash10-004i-1933000000-ec0486672b0ede4e7374	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 40V, Positive-QTOF	splash10-004i-6940000000-c10070d68baed2c2b567	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 10V, Negative-QTOF	splash10-000i-0109000000-3d14bcc6eb929d321836	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 20V, Negative-QTOF	splash10-004i-2924000000-9461161dbf9999532996	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoriin 40V, Negative-QTOF	splash10-00fs-1900000000-3c148183cdf12f6071e2	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

FDB002777

KNApSAcK ID

C00002458

Chemspider ID

4265025

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5088914

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1588631

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Cichoriin → 3,4,5-trihydroxy-6-[(2-oxo-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-6-yl)oxy]oxane-2-carboxylic acid	details

Showing metabocard for Cichoriin (HMDB0030821)

MOL for HMDB0030821 (Cichoriin)

3D MOL for HMDB0030821 (Cichoriin)

3D SDF for HMDB0030821 (Cichoriin)

3D-SDF for HMDB0030821 (Cichoriin)

PDB for HMDB0030821 (Cichoriin)

3D PDB for HMDB0030821 (Cichoriin)

SMILES for HMDB0030821 (Cichoriin)

INCHI for HMDB0030821 (Cichoriin)

Structure for HMDB0030821 (Cichoriin)

3D Structure for HMDB0030821 (Cichoriin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions