NP-MRD: Showing NP-Card for (2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid (NP0159809)

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Record Information

Version

2.0

Created at

2022-09-02 17:37:36 UTC

Updated at

2022-09-02 17:37:36 UTC

NP-MRD ID

NP0159809

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

Description

Luteolin 3'-methyl ether 7-glucuronosyl-(1->2)-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. Thus, luteolin 3'-methyl ether 7-glucuronosyl-(1->2)-glucuronide is considered to be a flavonoid. (2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid is found in Artemisia judaica, Medicago sativa and Medicago truncatula. Based on a literature review very few articles have been published on Luteolin 3'-methyl ether 7-glucuronosyl-(1->2)-glucuronide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219372D          

 46 50  0  0  1  0            999 V2000
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   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
   -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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   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   -1.2375    0.0000 C   0  0  2  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
    5.7158   -0.0000    0.0000 C   0  0  2  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
    5.0013    1.2375    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
    6.4302   -0.4125    0.0000 C   0  0  1  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 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
    5.7158   -1.6500    0.0000 C   0  0  1  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
    6.4302   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
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 17 18  1  0  0  0  0
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  1  1  0  0  0
 14 40  1  0  0  0  0
 40 41  2  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  0  0  0  0
  6 42  1  0  0  0  0
  5 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
  3 45  1  0  0  0  0
 45 46  1  0  0  0  0
M  END

     RDKit          3D

 74 78  0  0  0  0  0  0  0  0999 V2000
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    4.5103    1.9336   -4.2627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243    0.7948   -3.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406    0.1968   -2.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9761   -0.9353   -1.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3291   -1.5459   -0.8490 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8564   -2.6662   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2395   -3.2416    0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0843    1.3990    5.6515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6296   -0.3584    4.2445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5830   -0.3862    5.2755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2988   -0.5941    2.9313 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4603   -1.9930    2.7987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5124   -0.1123    1.7698 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0106    0.9936    1.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045    0.8320   -0.2269 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4501    1.7674   -0.9632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6586    1.6620   -2.3086 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9274    2.9872   -2.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1501    3.0944   -4.1455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9328    4.0971   -2.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9986    0.8117   -1.8933 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.5068    0.6711    0.4406 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5869   -1.5176    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2074   -1.0128   -0.3590 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1137   -1.4620   -2.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7223   -0.8623   -3.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1623    0.2616   -4.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7836    0.8314   -5.2714 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2843    3.5897   -4.1987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3205    2.6539   -2.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5394    0.6346   -2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7740   -3.1651   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4882   -4.7305    3.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 43  2  0
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 33 64  1  0
 21 56  1  0
 40 71  1  0
M  END


  Mrv1652309022219372D          

 46 50  0  0  1  0            999 V2000
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   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
   -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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   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   -1.2375    0.0000 C   0  0  2  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
    5.7158   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302   -0.4125    0.0000 C   0  0  1  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 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
    5.7158   -1.6500    0.0000 C   0  0  1  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
    6.4302   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   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
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  1  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 28 38  1  0  0  0  0
 38 39  1  1  0  0  0
 14 40  1  0  0  0  0
 40 41  2  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  0  0  0  0
  6 42  1  0  0  0  0
  5 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
  3 45  1  0  0  0  0
 45 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159809

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C(O)=O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O18/c1-41-14-4-8(2-3-10(14)29)13-7-12(31)16-11(30)5-9(6-15(16)43-13)42-28-24(20(35)19(34)23(45-28)26(39)40)46-27-21(36)17(32)18(33)22(44-27)25(37)38/h2-7,17-24,27-30,32-36H,1H3,(H,37,38)(H,39,40)/t17-,18-,19-,20-,21+,22-,23-,24+,27-,28+/m0/s1

> <INCHI_KEY>
MEUYKMSNZLTEBE-BBKSNKDASA-N

> <FORMULA>
C28H28O18

> <MOLECULAR_WEIGHT>
652.514

> <EXACT_MASS>
652.127564062

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
61.28454812618757

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
-0.8493367949999999

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.2212364444098505

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.599566553799945

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7322955043211996

> <JCHEM_POLAR_SURFACE_AREA>
288.65999999999997

> <JCHEM_REFRACTIVITY>
143.6696

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -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  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -0.770   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.004  -3.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.004  -7.700   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   45                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   43                                                  
CONECT    6    5    7   42                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   41                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   40                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   16   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   38                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   30   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   28   39                                                  
CONECT   39   38                                                            
CONECT   40   14   41                                                       
CONECT   41   40   10   42                                                  
CONECT   42   41    6                                                       
CONECT   43    5   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44    3   46                                                  
CONECT   46   45                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₈O₁₈

Average Mass

652.5140 Da

Monoisotopic Mass

652.12756 Da

IUPAC Name

(2S,3S,4S,5R,6S)-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-5-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C(O)=O)C=C2O1

InChI Identifier

InChI=1S/C28H28O18/c1-41-14-4-8(2-3-10(14)29)13-7-12(31)16-11(30)5-9(6-15(16)43-13)42-28-24(20(35)19(34)23(45-28)26(39)40)46-27-21(36)17(32)18(33)22(44-27)25(37)38/h2-7,17-24,27-30,32-36H,1H3,(H,37,38)(H,39,40)/t17-,18-,19-,20-,21+,22-,23-,24+,27-,28+/m0/s1

InChI Key

MEUYKMSNZLTEBE-BBKSNKDASA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Artemisia judaica	LOTUS Database	35616633
Medicago sativa	LOTUS Database	35616633
Medicago truncatula	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
3p-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Oxane
Hydroxy acid
Pyran
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Organoheterocyclic compound
Ether
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Oxacycle
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.86	ALOGPS
logP	-0.85	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	2.6	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	288.66 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	143.67 m³·mol⁻¹	ChemAxon
Polarizability	61.28 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00004346

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

102470743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

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References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid (NP0159809)

MOL for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D MOL for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D SDF for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

PDB for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D PDB for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

SMILES for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

INCHI for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

Structure for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D Structure for NP0159809 ((2s,3s,4s,5r,6s)-5-{[(2r,3r,4s,5s,6s)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3,4-dihydroxy-6-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)