NP-MRD: Showing NP-Card for 6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0211856)

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Record Information

Version

2.0

Created at

2022-09-05 10:18:33 UTC

Updated at

2022-09-05 10:18:33 UTC

NP-MRD ID

NP0211856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

6-{[2-(3,4-Dihydroxyphenyl)-3,5,6-trihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-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. 6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is found in Tanacetum parthenium. 6-{[2-(3,4-Dihydroxyphenyl)-3,5,6-trihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308201923362D          

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

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -6.2097   -1.8534    1.5601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3535   -0.9286    1.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1573   -0.3922    2.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5698   -0.4251    0.5469 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7178    0.5780    0.9969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8401    0.8521   -0.0692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4047   -0.3337   -0.6402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1184   -0.8300   -0.7405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157   -0.1805   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2733   -0.7020   -0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -0.0301    0.1078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5561   -0.4415    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5867    0.3965    0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1853    1.5920    1.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0886    2.4524    1.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4189    2.1133    1.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125    2.9381    2.3178 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8595    0.9386    1.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1893    0.5818    1.1722 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000    0.0843    0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360   -1.6436   -0.5604 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0129   -2.1799   -0.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6897   -2.4116   -1.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9321   -3.5023   -1.6418 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4078   -1.9307   -1.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3128   -2.6315   -1.5112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -3.8425   -2.1358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9475   -2.0451   -1.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0484   -2.7516   -1.8708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5963    1.7314   -1.0409 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3457    3.0637   -0.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0828    1.5017   -0.9823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6654    2.5018   -0.1737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4752    0.1460   -0.5207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7639    0.1828   -0.0051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8209    0.1810    3.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9709   -1.2869    0.1456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9837    1.4149    0.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144    0.7982    0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1347    1.8931    1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7664    3.3922    2.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1039    3.8127    2.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4613   -0.2772    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2904   -0.8207    0.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2270   -3.0530   -1.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999   -4.3707   -2.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8803   -3.6340   -2.3152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159    1.5160   -2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5471    3.1763   -0.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4895    1.6548   -2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2299    3.1157   -0.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4546   -0.5654   -1.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4307    0.4548   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 32  1  0
 32 30  1  0
 30 31  1  0
 30  6  1  0
  6  7  1  0
  7  8  1  0
  8 28  2  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 25  2  0
 25 10  1  0
 10 11  1  0
 11 12  1  0
 12 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 12 13  1  0
 13 20  2  0
 20 18  1  0
 18 19  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 10  9  2  0
  6  5  1  0
  5  4  1  0
  4 34  1  0
 34 35  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 34 32  1  0
  9  8  1  0
 23 25  1  0
 14 13  1  0
 33 51  1  0
 32 50  1  6
 30 48  1  6
 31 49  1  0
  6 38  1  1
 29 47  1  0
 27 46  1  0
 22 45  1  0
 20 44  1  0
 19 43  1  0
 17 42  1  0
 15 41  1  0
 14 40  1  0
  9 39  1  0
  4 37  1  6
 34 52  1  6
 35 53  1  0
  3 36  1  0
M  END


  Mrv1652308201923362D          

 35 38  0  0  0  0            999 V2000
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    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
    0.7145   -0.4125    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
    0.7145   -1.2375    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
    1.4289   -1.6500    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
    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
   -2.8579    0.0000    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
   -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 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
    5.0013    1.2375    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
   -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 O   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
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
   -2.8579    0.8250    0.0000 O   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
   -3.5724   -2.8875    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
   -1.4289    0.0000    0.0000 O   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
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  2  0  0  0  0
  9  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 14  1  0  0  0  0
 18  5  1  0  0  0  0
 18 15  2  0  0  0  0
 19 16  1  0  0  0  0
 20 19  1  0  0  0  0
 21 17  1  0  0  0  0
 22  6  1  0  0  0  0
 23  7  1  0  0  0  0
 24 11  1  0  0  0  0
 25 12  1  0  0  0  0
 26 13  2  0  0  0  0
 27 14  1  0  0  0  0
 28 15  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  1  0  0  0  0
 31 20  2  0  0  0  0
 32 20  1  0  0  0  0
 33  8  1  0  0  0  0
 33 18  1  0  0  0  0
 34  9  1  0  0  0  0
 34 21  1  0  0  0  0
 35 19  1  0  0  0  0
 35 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C(OC2=C(O)C(O)=C3C(OC(=C(O)C3=O)C3=CC(O)=C(O)C=C3)=C2)OC(C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O14/c22-6-2-1-5(3-7(6)23)18-15(28)13(26)10-8(33-18)4-9(11(24)12(10)25)34-21-17(30)14(27)16(29)19(35-21)20(31)32/h1-4,14,16-17,19,21-25,27-30H,(H,31,32)

> <INCHI_KEY>
PPLHNQARCNPIOF-UHFFFAOYSA-N

> <FORMULA>
C21H18O14

> <MOLECULAR_WEIGHT>
494.361

> <EXACT_MASS>
494.06965526

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.919735421342416

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.16

> <JCHEM_LOGP>
-0.0950594129999997

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.287502421457883

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6005388240895266

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9549070784807823

> <JCHEM_POLAR_SURFACE_AREA>
243.89999999999995

> <JCHEM_REFRACTIVITY>
110.85489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-AUG-19         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -6.668  -5.390   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
HETATM   34  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    5    7                                                       
CONECT    4    8    9                                                       
CONECT    5    1    3   18                                                  
CONECT    6    2    7   22                                                  
CONECT    7    3    6   23                                                  
CONECT    8    4   10   33                                                  
CONECT    9    4   11   34                                                  
CONECT   10    8   12   13                                                  
CONECT   11    9   12   24                                                  
CONECT   12   10   11   25                                                  
CONECT   13   10   15   26                                                  
CONECT   14   16   17   27                                                  
CONECT   15   13   18   28                                                  
CONECT   16   14   19   29                                                  
CONECT   17   14   21   30                                                  
CONECT   18    5   15   33                                                  
CONECT   19   16   20   35                                                  
CONECT   20   19   31   32                                                  
CONECT   21   17   34   35                                                  
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24   11                                                            
CONECT   25   12                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   15                                                            
CONECT   29   16                                                            
CONECT   30   17                                                            
CONECT   31   20                                                            
CONECT   32   20                                                            
CONECT   33    8   18                                                       
CONECT   34    9   21                                                       
CONECT   35   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₁H₁₈O₁₄

Average Mass

494.3610 Da

Monoisotopic Mass

494.06966 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1C(O)C(OC2=C(O)C(O)=C3C(OC(=C(O)C3=O)C3=CC(O)=C(O)C=C3)=C2)OC(C1O)C(O)=O

InChI Identifier

InChI=1S/C21H18O14/c22-6-2-1-5(3-7(6)23)18-15(28)13(26)10-8(33-18)4-9(11(24)12(10)25)34-21-17(30)14(27)16(29)19(35-21)20(31)32/h1-4,14,16-17,19,21-25,27-30H,(H,31,32)

InChI Key

PPLHNQARCNPIOF-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
Tanacetum parthenium	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-hydroxyflavone
Hydroxyflavonoid
Flavone
3'-hydroxyflavonoid
6-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Chromone
O-glycosyl compound
Glycosyl compound
1-benzopyran
Benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
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	1.16	ALOGPS
logP	-0.095	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.6	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	243.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.85 m³·mol⁻¹	ChemAxon
Polarizability	44.92 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0128159

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB087015

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

131834509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (NP0211856)

MOL for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for NP0211856 (6-{[2-(3,4-dihydroxyphenyl)-3,5,6-trihydroxy-4-oxochromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)