NP-MRD: Showing NP-Card for Luteolin 3'-O-beta-D-glucuronide (NP0052606)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Show more...Show more...

Record Information

Version

2.0

Created at

2022-04-27 23:35:48 UTC

Updated at

2022-04-27 23:35:48 UTC

NP-MRD ID

NP0052606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luteolin 3'-O-beta-D-glucuronide

Description

Luteolin 3'-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. Luteolin 3'-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Luteolin 3'-O-beta-D-glucuronide is found in Conocephalum conicum, Elsholtzia rugulosa Hemsl., Enhalus acoroides, Lunularia cruciata, Salvia officinalis , Rosmarinus officinalis and Thymus vulgaris. A luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 3'-position.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652310111917572D          

 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
    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
    6.4302   -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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  2  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
    7.1447   -1.6500    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
    8.5737    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    7.1447   -0.0000    0.0000 O   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
    7.8592    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    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  4  1  0  0  0  0
 11  6  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14  5  2  0  0  0  0
 15 10  2  0  0  0  0
 15 11  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  8  1  0  0  0  0
 23  9  1  0  0  0  0
 24 10  1  0  0  0  0
 25 11  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 12  1  0  0  0  0
 31 14  1  0  0  0  0
 32 13  1  0  0  0  0
 21 32  1  6  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

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
   -5.5254    0.1778    1.9999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4892    1.0011    1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6818    1.4101    0.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    1.5228    0.5578 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1167    1.0144    1.2145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4817   -0.0679    0.6335 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0724   -1.0365    1.5327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983   -1.4633    1.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3362   -0.9770    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6069   -1.4417    1.5079 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7826   -0.8862    0.8187 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -1.2934    1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1730   -0.7633    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3244   -1.1580    0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9582    0.2121   -0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9871    0.8021   -1.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2749    0.4648   -1.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6491    1.7881   -2.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680    2.1845   -2.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0789    3.1764   -3.3803 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3706    1.5775   -1.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437    0.5866   -0.7484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475    0.0446   -0.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6951   -2.4185    2.4647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -2.9211    3.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7050   -2.4635    2.7869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466   -2.9579    3.4081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3315   -0.7493   -0.4225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5280   -1.7933   -0.9382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5370    0.2612   -1.5310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3048   -0.2669   -2.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1416    1.4832   -0.9366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5442    2.6094   -1.5051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3859    0.7164    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2203    2.6274    0.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6028    0.3426    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2755   -0.2142    0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2613   -2.0579    1.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7327   -0.1530   -0.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4852    2.2328   -2.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121    2.8335   -4.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3309    1.8537   -1.8599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6642   -2.8063    2.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6420   -3.6999    3.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7361   -2.5953    3.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2663   -1.1584   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -1.4414   -1.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5207    0.5184   -1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8995    0.4211   -2.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2177    1.5154   -1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9920    3.4062   -1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
  7  8  1  0
  8 26  2  0
 26 27  1  0
 26 25  1  0
 25 24  2  0
 24 10  1  0
 10  9  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  4 32  1  0
 32 33  1  0
 32 30  1  0
 30 31  1  0
 30 28  1  0
 28 29  1  0
 28  6  1  0
  9  8  1  0
 23 11  1  0
 22 15  1  0
  6 36  1  6
 27 45  1  0
 25 44  1  0
 24 43  1  0
  9 37  1  0
 12 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
  4 35  1  6
  3 34  1  0
 32 50  1  6
 33 51  1  0
 30 48  1  6
 31 49  1  0
 28 46  1  1
 29 47  1  0
M  END

  Mrv1652310111917572D          

 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
    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
    6.4302   -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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  2  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
    7.1447   -1.6500    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
    8.5737    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    7.1447   -0.0000    0.0000 O   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
    7.8592    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    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  4  1  0  0  0  0
 11  6  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14  5  2  0  0  0  0
 15 10  2  0  0  0  0
 15 11  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  8  1  0  0  0  0
 23  9  1  0  0  0  0
 24 10  1  0  0  0  0
 25 11  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 12  1  0  0  0  0
 31 14  1  0  0  0  0
 32 13  1  0  0  0  0
 21 32  1  6  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>
NP0052606

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(OC2=C(O)C=CC(=C2)C2=CC(=O)C3=C(O)C=C(O)C=C3O2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

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

> <FORMULA>
C21H18O12

> <MOLECULAR_WEIGHT>
462.363

> <EXACT_MASS>
462.07982602

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
43.13875076162755

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-6-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
0.4553302566666667

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.576376193671885

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.960277024101365

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686827977168856

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999994

> <JCHEM_REFRACTIVITY>
106.90659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-6-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

> <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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -0.770   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      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.337  -3.080   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      16.004   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      16.004   1.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0      14.670   5.390   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      12.003   5.390   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      14.670   0.770   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      13.337   3.080   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      12.003   0.770   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1    9                                                       
CONECT    3    7   13                                                       
CONECT    4    8   10                                                       
CONECT    5    8   14                                                       
CONECT    6   11   12                                                       
CONECT    7    1    3   12                                                  
CONECT    8    4    5   22                                                  
CONECT    9    2   13   23                                                  
CONECT   10    4   15   24                                                  
CONECT   11    6   15   25                                                  
CONECT   12    6    7   31                                                  
CONECT   13    3    9   32                                                  
CONECT   14    5   15   31                                                  
CONECT   15   10   11   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   32   33   38                                             
CONECT   22    8                                                            
CONECT   23    9                                                            
CONECT   24   10                                                            
CONECT   25   11                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   20                                                            
CONECT   30   20                                                            
CONECT   31   12   14                                                       
CONECT   32   13   21                                                       
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
Luteolin 3'-O-beta-D-glucopyranosiduronic acid	ChEBI
Luteolin 3'-O-beta-D-glucoronopyranoside	ChEBI
Luteolin 3'-O-b-D-glucopyranosiduronate	Generator
Luteolin 3'-O-b-D-glucopyranosiduronic acid	Generator
Luteolin 3'-O-beta-D-glucopyranosiduronate	Generator
Luteolin 3'-O-β-D-glucopyranosiduronate	Generator
Luteolin 3'-O-β-D-glucopyranosiduronic acid	Generator
Luteolin 3'-O-b-D-glucoronopyranoside	Generator
Luteolin 3'-O-β-D-glucoronopyranoside	Generator
Luteolin 3'-O-beta-D-glucuronide	MeSH
Luteolin 3'-glucuronide	ChEBI

Chemical Formula

C₂₁H₁₈O₁₂

Average Mass

462.3630 Da

Monoisotopic Mass

462.07983 Da

IUPAC Name

(2S,3S,4S,5R,6S)-6-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(OC2=C(O)C=CC(=C2)C2=CC(=O)C3=C(O)C=C(O)C=C3O2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

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

JDOFZOKGCYYUER-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
Conocephalum conicum	Plant	KNApSAcK
Elsholtzia rugulosa Hemsl.	Plant	KNApSAcK
Enhalus acoroides	Plant	KNApSAcK
Lunularia cruciata	Plant	KNApSAcK
Salvia officinalis	Plant	KNApSAcK
Salvia rosmarinus	Plant	KNApSAcK
Thymus vulgaris	LOTUS Database	35616633

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-3p-o-glucuronide
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Phenol ether
Phenoxy compound
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Pyran
Hydroxy acid
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous acid
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:75726 )
luteolin O-glucuronoside (CHEBI:75726 )

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)	2.96	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	43.14 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

HMDB0240540

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093734

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10253785

PDB ID

Not Available

ChEBI ID

75726

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Luteolin 3'-O-beta-D-glucuronide (NP0052606)

MOL for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

3D MOL for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

3D SDF for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

3D-SDF for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

PDB for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

3D PDB for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

SMILES for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

INCHI for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

Structure for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)

3D Structure for NP0052606 (Luteolin 3'-O-beta-D-glucuronide)