NP-MRD: Showing NP-Card for Luteolin 5-glucuronide (NP0052600)

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Record Information

Version

2.0

Created at

2022-04-27 23:35:09 UTC

Updated at

2022-04-27 23:35:09 UTC

NP-MRD ID

NP0052600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luteolin 5-glucuronide

Description

Luteolin 5-O-glucuronide belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid. Thus, luteolin 5-O-glucuronide is considered to be a flavonoid. Luteolin 5-O-glucuronide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Luteolin 5-glucuronide is found in Dumortiera hirsuta and Torilis arvensis . Based on a literature review very few articles have been published on luteolin 5-O-glucuronide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201352D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    3.5724    1.2375    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
    4.2868   -0.0000    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  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
   -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  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  2  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
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  3 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  1  0  0  0
 23 31  1  6  0  0  0
 22 32  1  1  0  0  0
  1 33  1  0  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -5.1389   -1.0340   -2.6808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6638   -0.9213   -1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0157   -1.1715   -1.4152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477   -0.5283   -0.3783 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5281   -0.3362   -0.7738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8641    0.5480    0.0950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5111    0.3422   -0.0967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6483   -0.0128    0.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9255   -0.2316    2.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500   -0.5955    3.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -0.8070    4.4332 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3356   -0.7391    2.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.5327    1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161   -0.6797    0.9872 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3274   -0.5009   -0.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7380   -0.6946   -0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6193   -1.0613    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9570   -1.2534    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4827   -1.0906   -1.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8371   -1.2904   -1.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6376   -0.7283   -2.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1241   -0.5561   -3.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2789   -0.5381   -1.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3918   -0.1419   -1.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.0269   -0.8296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284    0.3544   -1.6997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6906   -0.1761    0.4916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3297    1.9321   -0.3122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7528    2.9219    0.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8266    1.9715   -0.1031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4182    2.3880   -1.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4135    0.6732    0.3336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4065    0.4890    1.7169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5132   -1.0784   -0.5457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8449   -1.3674    0.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474    0.3879    1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9327   -0.1218    2.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -0.1019    5.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276   -1.0240    3.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1982   -1.1874    1.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6339   -1.5424    1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2011   -1.1665   -2.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5146   -0.2907   -4.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6660   -0.2576   -2.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7121    0.0111   -2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    2.1212   -1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9185    3.2288    0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1183    2.7475    0.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2937    3.3610   -1.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5080    0.7031    0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2853   -0.4484    1.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 28  1  0
 28 29  1  0
 28  6  1  0
  6  7  1  0
  7  8  1  0
  8 27  2  0
 27 25  1  0
 25 26  2  0
 25 24  1  0
 24 15  2  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  2  0
  6  5  1  0
  5  4  1  0
  4 32  1  0
 32 33  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 32 30  1  0
  9  8  1  0
 23 16  1  0
 13 27  1  0
 31 49  1  0
 30 48  1  1
 28 46  1  6
 29 47  1  0
  6 36  1  1
 24 45  1  0
 12 39  1  0
 11 38  1  0
  9 37  1  0
 17 40  1  0
 18 41  1  0
 20 42  1  0
 22 43  1  0
 23 44  1  0
  4 35  1  1
 32 50  1  6
 33 51  1  0
  3 34  1  0
M  END


  Mrv1652304282201352D          

 33 36  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    3.5724    1.2375    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
    4.2868   -0.0000    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  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
   -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  2  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  2  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
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    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
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
  3 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  6  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  1  0  0  0
 23 31  1  6  0  0  0
 22 32  1  1  0  0  0
  1 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052600

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O12/c22-8-4-13-15(11(25)6-12(31-13)7-1-2-9(23)10(24)3-7)14(5-8)32-21-18(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>
FPKBUYIIWUFWOS-ZFORQUDYSA-N

> <FORMULA>
C21H18O12

> <MOLECULAR_WEIGHT>
462.363

> <EXACT_MASS>
462.07982602

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.31956811097155

> <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)-7-hydroxy-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
-0.19466974333333334

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.525837535502915

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7596473894920655

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686827061663977

> <JCHEM_POLAR_SURFACE_AREA>
203.44

> <JCHEM_REFRACTIVITY>
106.90659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.52e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   33                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16                                                            
CONECT   19   15                                                            
CONECT   20    3   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   32                                                  
CONECT   23   22   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24                                                            
CONECT   31   23                                                            
CONECT   32   22                                                            
CONECT   33    1                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Luteolin 5-glucuronide	ChEBI
Luteolin 5-O-beta-D-glucopyranosiduronic acid	ChEBI
Luteolin 5-O-beta-D-glucoronopyranoside	ChEBI
Luteolin 5-O-b-D-glucopyranosiduronate	Generator
Luteolin 5-O-b-D-glucopyranosiduronic acid	Generator
Luteolin 5-O-beta-D-glucopyranosiduronate	Generator
Luteolin 5-O-β-D-glucopyranosiduronate	Generator
Luteolin 5-O-β-D-glucopyranosiduronic acid	Generator
Luteolin 5-O-b-D-glucoronopyranoside	Generator
Luteolin 5-O-β-D-glucoronopyranoside	Generator

Chemical Formula

C₂₁H₁₈O₁₂

Average Mass

462.3630 Da

Monoisotopic Mass

462.07983 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H18O12/c22-8-4-13-15(11(25)6-12(31-13)7-1-2-9(23)10(24)3-7)14(5-8)32-21-18(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

FPKBUYIIWUFWOS-ZFORQUDYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dumortiera hirsuta	LOTUS Database	35616633
Torilis arvensis	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glucuronides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:75727 )
luteolin O-glucuronoside (CHEBI:75727 )

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	1.23	ALOGPS
logP	-0.19	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.76	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	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	43.32 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30785679

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72193663

PDB ID

Not Available

ChEBI ID

75727

Good Scents ID

Not Available

References

General References

Showing NP-Card for Luteolin 5-glucuronide (NP0052600)

MOL for NP0052600 (Luteolin 5-glucuronide)

3D MOL for NP0052600 (Luteolin 5-glucuronide)

3D SDF for NP0052600 (Luteolin 5-glucuronide)

3D-SDF for NP0052600 (Luteolin 5-glucuronide)

PDB for NP0052600 (Luteolin 5-glucuronide)

3D PDB for NP0052600 (Luteolin 5-glucuronide)

SMILES for NP0052600 (Luteolin 5-glucuronide)

INCHI for NP0052600 (Luteolin 5-glucuronide)

Structure for NP0052600 (Luteolin 5-glucuronide)

3D Structure for NP0052600 (Luteolin 5-glucuronide)