NP-MRD: Showing NP-Card for Luteolin 7-glucuronide (NP0049129)

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Record Information

Version

2.0

Created at

2022-03-17 21:07:35 UTC

Updated at

2022-03-17 21:07:35 UTC

NP-MRD ID

NP0049129

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luteolin 7-glucuronide

Description

Luteolin 7-glucuronide belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Luteolin 7-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Luteolin 7-glucuronide is found, on average, in the highest concentration within globe artichokes and lettuces. Luteolin 7-glucuronide has also been detected, but not quantified in, several different foods, such as common sages, common oregano, chicories, wild carrots, and common thymes. This could make luteolin 7-glucuronide a potential biomarker for the consumption of these foods. Luteolin 7-glucuronide is found in Acanthus ebracteatus, Achillea collina, Agrimonia eupatoria, Antirrhinum majus , Apis cerana, Chaenomeles sinensis, Chaerophyllum aureum, Chrysanthemum indicum, Chrysanthemum morifolium, Cynara cardunculus, Dumortiera hirsuta, Fuchsia excorticata , Fuchsia procumbens, Hebe parviflora, Lactuca indica , Lapsana communis, Lippia alba , Lycopus europaeus, Lycopus exaltatus, Marchantia berteroana, Marchantia polymorpha, Marrubium vulgare, Medicago arabica, Medicago polymorpha , Medicago radiata, Medicago sativa, Medicago truncatula, Meehania fargesii, Meehania urticifolia, Monarda punctata, Pedicularis longiflora var. tubiformis, Perilla frutescens, Phagnalon rupestre, Picria fel-terrae , Plantago asiatica, Plantago major , Potentilla anserina, Rhizomnium pseudopunctatum, Riccia fluitans, Riccia fluitans L, Rubus ulmifolius, Salvia fruticosa, Salvia palaestina, Salvia pratensis , Salvia triloba , Santolina chamaecyperissus, Leontodon autumnalis, Sonchus mauritanicus, Sonchus schweinfurthii, Sphaerocarpos texanus, Stachys alopecuros (L.) Benth., Stachys officinalis (L.) Trev. , Tanacetum parthenium, Tanacetum parthenium (L.) Schulz Bip. , Torilis tenella, Trifolium pannonicum, Tripora divaricata, Gymnanthemum amygdalinum, Veronica parviflora, Vitex trifolia and Youngia japonica. Luteolin 7-glucuronide was first documented in 1992 (PMID: 1620743). A luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position (PMID: 12088434) (PMID: 7766058).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310111917592D          

 38 41  0  0  1  0            999 V2000
    5.0013   -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
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -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
    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
    4.2868    0.0000    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  5  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25 12  2  0  0  0  0
 16 26  1  6  0  0  0
 17 27  1  1  0  0  0
 18 28  1  1  0  0  0
 29 20  2  0  0  0  0
 30 20  1  0  0  0  0
 31  8  1  0  0  0  0
 21 31  1  6  0  0  0
 32 13  1  0  0  0  0
 32 14  1  0  0  0  0
 33 19  1  0  0  0  0
 33 21  1  0  0  0  0
 16 34  1  1  0  0  0
 17 35  1  6  0  0  0
 18 36  1  6  0  0  0
 19 37  1  1  0  0  0
 21 38  1  1  0  0  0
M  END


  Mrv1652310111917592D          

 38 41  0  0  1  0            999 V2000
    5.0013   -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
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -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
    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
    4.2868    0.0000    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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
    7.1447   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 14  5  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 10  1  0  0  0  0
 24 11  1  0  0  0  0
 25 12  2  0  0  0  0
 16 26  1  6  0  0  0
 17 27  1  1  0  0  0
 18 28  1  1  0  0  0
 29 20  2  0  0  0  0
 30 20  1  0  0  0  0
 31  8  1  0  0  0  0
 21 31  1  6  0  0  0
 32 13  1  0  0  0  0
 32 14  1  0  0  0  0
 33 19  1  0  0  0  0
 33 21  1  0  0  0  0
 16 34  1  1  0  0  0
 17 35  1  6  0  0  0
 18 36  1  6  0  0  0
 19 37  1  1  0  0  0
 21 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0049129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=C(O)C=C2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

> <INCHI_KEY>
VSUOKLTVXQRUSG-ZFORQUDYSA-N

> <FORMULA>
C21H18O12

> <MOLECULAR_WEIGHT>
462.3604

> <EXACT_MASS>
462.07982604

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
42.87309712388788

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
0.4553302566666667

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.296838373138155

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7391979384789353

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686826778068572

> <JCHEM_POLAR_SURFACE_AREA>
203.44

> <JCHEM_REFRACTIVITY>
106.90659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luteolin 7-O-glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-OCT-19         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0       0.000  -6.160   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.667  -6.160   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   11                                                       
CONECT    5    8   14                                                       
CONECT    6   12   13                                                       
CONECT    7    1    3   13                                                  
CONECT    8    4    5   31                                                  
CONECT    9    2   10   22                                                  
CONECT   10    3    9   23                                                  
CONECT   11    4   15   24                                                  
CONECT   12    6   15   25                                                  
CONECT   13    6    7   32                                                  
CONECT   14    5   15   32                                                  
CONECT   15   11   12   14                                                  
CONECT   16   17   18   26   34                                             
CONECT   17   16   19   27   35                                             
CONECT   18   16   21   28   36                                             
CONECT   19   17   20   33   37                                             
CONECT   20   19   29   30                                                  
CONECT   21   18   31   33   38                                             
CONECT   22    9                                                            
CONECT   23   10                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   20                                                            
CONECT   30   20                                                            
CONECT   31    8   21                                                       
CONECT   32   13   14                                                       
CONECT   33   19   21                                                       
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   19                                                            
CONECT   38   21                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Cyanidenon-7-O-beta-D-glucuronic acid	ChEBI
Luteolin 7-O-beta-D-glucuronopyranoside	ChEBI
Luteolin 7-O-glucuronide	ChEBI
Luteolin 7-O-beta-D-glucuronide	Kegg
Cyanidenon-7-O-b-D-glucuronate	Generator
Cyanidenon-7-O-b-D-glucuronic acid	Generator
Cyanidenon-7-O-beta-D-glucuronate	Generator
Cyanidenon-7-O-β-D-glucuronate	Generator
Cyanidenon-7-O-β-D-glucuronic acid	Generator
Luteolin 7-O-b-D-glucuronopyranoside	Generator
Luteolin 7-O-β-D-glucuronopyranoside	Generator
Luteolin 7-O-b-D-glucuronide	Generator
Luteolin 7-O-β-D-glucuronide	Generator
Luteolin-7-glucuronide	MeSH
Luteolin 7-glucuronide	ChEBI

Chemical Formula

C₂₁H₁₈O₁₂

Average Mass

462.3604 Da

Monoisotopic Mass

462.07983 Da

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

luteolin 7-O-glucuronide

CAS Registry Number

29741-10-4

SMILES

[H][C@@]1(OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC(O)=C(O)C=C2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

InChI Key

VSUOKLTVXQRUSG-ZFORQUDYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthus ebracteatus	Plant	KNApSAcK
Achillea collina	LOTUS Database	35616633
Agrimonia eupatoria	LOTUS Database	35616633
Antirrhinum majus	Plant	KNApSAcK
Apis cerana	LOTUS Database	35616633
Chaenomeles sinensis	LOTUS Database	35616633
Chaerophyllum aureum	LOTUS Database	35616633
Chrysanthemum indicum	LOTUS Database	35616633
Chrysanthemum morifolium	LOTUS Database	35616633
Cichorium endivia	FooDB	PHENOL EXPLORER
Cichorium intybus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cynara cardunculus	LOTUS Database	35616633
Cynara scolymus	FooDB	PHENOL EXPLORER
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Dumortiera hirsuta	LOTUS Database	35616633
Fuchsia excorticata	Plant	KNApSAcK
Fuchsia procumbens	Plant	KNApSAcK
Hebe parviflora	Plant	KNApSAcK
Lactuca indica	Plant	KNApSAcK
Lactuca sativa	FooDB	PHENOL EXPLORER
Lapsana communis L.	LOTUS Database	35616633
Lippia alba	Plant	KNApSAcK
Lycopus europaeus	LOTUS Database	35616633
Lycopus exaltatus	LOTUS Database	35616633
Marchantia berteroana	Plant	KNApSAcK
Marchantia polymorpha	Plant	KNApSAcK
Marrubium vulgare	LOTUS Database	35616633
Medicago arabica	Plant	KNApSAcK
Medicago polymorpha	Plant	KNApSAcK
Medicago radiata	Plant	KNApSAcK
Medicago sativa	LOTUS Database	35616633
Medicago truncatula	LOTUS Database	35616633
Meehania fargesii	LOTUS Database	35616633
Meehania urticifolia	LOTUS Database	35616633
Monarda punctata	LOTUS Database	35616633
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pedicularis longiflora var. tubiformis	Plant	KNApSAcK
Perilla frutescens	LOTUS Database	35616633
Phagnalon rupestre	LOTUS Database	35616633
Picria fel-terrae	Plant	KNApSAcK
Plantago asiatica	LOTUS Database	35616633
Plantago major	Plant	KNApSAcK
Potentilla anserina	LOTUS Database	35616633
Rhizomnium pseudopunctatum	LOTUS Database	35616633
Riccia fluitans	LOTUS Database	35616633
Riccia fluitans L	Plant	KNApSAcK
Rubus ulmifolius	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia palaestina	Plant	KNApSAcK
Salvia pratensis	Plant	KNApSAcK
Salvia triloba	Plant	KNApSAcK
Santolina chamaecyperissus	Plant	KNApSAcK
Scorzoneroides autumnalis	Plant	KNApSAcK
Sonchus mauritanicus	LOTUS Database	35616633
Sonchus schweinfurthii	LOTUS Database	35616633
Sphaerocarpos texanus	-	KNApSAcK
Stachys alopecuros	Plant	KNApSAcK
Stachys officinalis (L.) Trev.	Plant	KNApSAcK
Tanacetum parthenium	LOTUS Database	35616633
Tanacetum parthenium (L.) Schulz Bip.	Plant	KNApSAcK
Thymus vulgaris	FooDB	KNAPSACK
Torilis tenella	LOTUS Database	35616633
Trifolium pannonicum	LOTUS Database	35616633
Tripora divaricata	Plant	KNApSAcK
Vernonia amygdalina	LOTUS Database	35616633
Veronica parviflora	LOTUS Database	35616633
Vitex trifolia	LOTUS Database	35616633
Youngia japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
Beta-hydroxy acid
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:18128 )
glycosyloxyflavone (CHEBI:18128 )
trihydroxyflavone (CHEBI:18128 )
luteolin O-glucuronoside (CHEBI:18128 )
flavones (C03515 )
Flavones and Flavonols (C03515 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.22	ALOGPS
logP	0.46	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.74	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.91 m³·mol⁻¹	ChemAxon
Polarizability	42.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0240541

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017828

KNApSAcK ID

C00004268

Chemspider ID

Not Available

KEGG Compound ID

C03515

BioCyc ID

LUTEOLIN-7-O-BETA-D-GLUCURONIDE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280601

PDB ID

Not Available

ChEBI ID

18128

Good Scents ID

Not Available

References

General References

Dapkevicius A, van Beek TA, Lelyveld GP, van Veldhuizen A, de Groot A, Linssen JP, Venskutonis R: Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves. J Nat Prod. 2002 Jun;65(6):892-6. doi: 10.1021/np010636j. [PubMed:12088434 ]
Gumbinger HG, Winterhoff H, Wylde R, Sosa A: On the influence of the sugar moiety on the antigonadotropic activity of luteoline glycosides. Planta Med. 1992 Feb;58(1):49-50. doi: 10.1055/s-2006-961388. [PubMed:1620743 ]
Williams CA, Hoult JR, Harborne JB, Greenham J, Eagles J: A biologically active lipophilic flavonol from Tanacetum parthenium. Phytochemistry. 1995 Jan;38(1):267-70. doi: 10.1016/0031-9422(94)00609-w. [PubMed:7766058 ]

Showing NP-Card for Luteolin 7-glucuronide (NP0049129)

MOL for NP0049129 (Luteolin 7-glucuronide)

3D MOL for NP0049129 (Luteolin 7-glucuronide)

3D SDF for NP0049129 (Luteolin 7-glucuronide)

3D-SDF for NP0049129 (Luteolin 7-glucuronide)

PDB for NP0049129 (Luteolin 7-glucuronide)

3D PDB for NP0049129 (Luteolin 7-glucuronide)

SMILES for NP0049129 (Luteolin 7-glucuronide)

INCHI for NP0049129 (Luteolin 7-glucuronide)

Structure for NP0049129 (Luteolin 7-glucuronide)

3D Structure for NP0049129 (Luteolin 7-glucuronide)