NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid (NP0311079)

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Record Information

Version

2.0

Created at

2022-09-11 06:50:20 UTC

Updated at

2022-09-11 06:50:20 UTC

NP-MRD ID

NP0311079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

Description

3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid 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. 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid is found in Centaurea jacea. 3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261503252D          

 34 37  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   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
    2.8579   -1.6500    0.0000 C   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   -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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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 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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
  4 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    5.2652   -2.2066   -2.3253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8550   -2.2860   -0.9486 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7434   -1.5365   -0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7860   -0.2696   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0409    0.4807    0.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9073    1.8520    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0255    2.5964    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2929    2.0590    0.6375 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4193    2.8389    0.9030 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3862    0.7086    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2733   -0.0968    0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6374    0.3457    0.1571 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -0.1810    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2993    0.4930    0.3169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9738   -0.0527    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0823    0.6629    0.4877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4088    0.2751    0.4014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0316    1.1650   -0.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3380    0.8500   -0.7433 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1754    2.0485   -0.6692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6456    3.1566   -0.3959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5485    2.0490   -0.8847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8685   -0.2926    0.0916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2422   -0.3527   -0.1239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5077   -0.1946    1.5370 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4535    0.4865    2.3019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1434    0.3964    1.7289 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2625    1.7553    2.0038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0743   -1.3327   -0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0820   -2.0582   -0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088   -3.3585   -1.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122   -1.4687   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4754   -2.1343   -0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004   -3.3125   -1.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6630   -2.9074   -2.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1029   -1.1794   -2.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3653   -2.4066   -2.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9117    2.3248    0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9296    3.6677    0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6811    2.9280    1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3472    0.2335    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4198   -1.1621   -0.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532    1.5189    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4823   -0.7551    0.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3810    0.4890   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2171    1.9747   -0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4405   -1.2311   -0.3171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5866   -1.2531   -0.2415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4869   -1.2462    1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1251   -0.1389    2.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6282   -0.1150    2.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5151    1.9108    2.9498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890   -1.8805   -0.4759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8352   -3.8575   -1.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 15 29  2  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 32 33  1  0
 33 34  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 33  3  1  0
 11  5  1  0
 32 13  1  0
 27 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
 14 43  1  0
 17 44  1  6
 19 45  1  6
 23 47  1  6
 24 48  1  0
 25 49  1  1
 26 50  1  0
 27 51  1  1
 28 52  1  0
 22 46  1  0
 29 53  1  0
 31 54  1  0
  6 38  1  0
  7 39  1  0
  9 40  1  0
 10 41  1  0
 11 42  1  0
M  END


  Mrv1533004261503252D          

 34 37  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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 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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    7.1447   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 O   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
    2.8579   -1.6500    0.0000 C   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   -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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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 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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
  4 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2=CC(OC3OC(C(O)C(O)C3O)C(O)=O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O12/c1-31-19-14(25)13-11(24)6-10(7-12(13)33-18(19)8-2-4-9(23)5-3-8)32-22-17(28)15(26)16(27)20(34-22)21(29)30/h2-7,15-17,20,22-24,26-28H,1H3,(H,29,30)

> <INCHI_KEY>
DKWQRYDJKSHULB-UHFFFAOYSA-N

> <FORMULA>
C22H20O12

> <MOLECULAR_WEIGHT>
476.39

> <EXACT_MASS>
476.095476084

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
45.119681737156704

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
0.6248986196666674

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.088879716527909

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.719942395115593

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686826778068572

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
111.64429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18                                                  
CONECT   18   17                                                            
CONECT   19   12   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    8   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    6   26                                                  
CONECT   26   25    3   27                                                  
CONECT   27   26                                                            
CONECT   28    4   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₂₂H₂₀O₁₂

Average Mass

476.3900 Da

Monoisotopic Mass

476.09548 Da

IUPAC Name

3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=C(OC2=CC(OC3OC(C(O)C(O)C3O)C(O)=O)=CC(O)=C2C1=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C22H20O12/c1-31-19-14(25)13-11(24)6-10(7-12(13)33-18(19)8-2-4-9(23)5-3-8)32-22-17(28)15(26)16(27)20(34-22)21(29)30/h2-7,15-17,20,22-24,26-28H,1H3,(H,29,30)

InChI Key

DKWQRYDJKSHULB-UHFFFAOYSA-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
Centaurea jacea	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-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
3-methoxychromone
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Beta-hydroxy acid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Pyranone
Oxane
Monosaccharide
Pyran
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Polyol
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Ether
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
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	1.1	ALOGPS
logP	0.62	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.64 m³·mol⁻¹	ChemAxon
Polarizability	45.12 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

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

74978412

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid (NP0311079)

MOL for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D MOL for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D SDF for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

PDB for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D PDB for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

SMILES for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

INCHI for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

Structure for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D Structure for NP0311079 (3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-3-methoxy-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)