NP-MRD: Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate (NP0216908)

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Record Information

Version

2.0

Created at

2022-09-05 17:03:23 UTC

Updated at

2022-09-05 17:03:23 UTC

NP-MRD ID

NP0216908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

Description

2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate is found in Anemone nemorosa. Based on a literature review very few articles have been published on 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052219032D          

 34 37  0  0  1  0            999 V2000
    0.7145   -2.8875    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
    0.0000   -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
    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
   -0.7145    2.0625    0.0000 O   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
    1.4289    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
    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
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25  2  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    0.9977   -1.7728   -0.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1651   -0.6749   -0.7401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529    0.0669   -1.1289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1980   -0.4750   -0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.0936    0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7186    0.9390    1.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6465    1.7701    1.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4021    2.7285    2.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316    2.8723    3.0975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9633    3.8329    4.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3168    2.0442    3.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778    2.1743    4.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535    1.1063    2.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2007   -0.7220    0.2325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6154   -1.6562   -0.5414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8320   -2.2929   -0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2636   -3.2911   -1.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4793   -3.9311   -1.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4182   -3.6686   -2.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1932   -3.0769   -2.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3568   -3.4532   -3.4681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8003   -2.0703   -1.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745   -1.4940   -1.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -1.8553   -2.7183 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5605   -0.1792   -0.9591 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4719    1.0491   -1.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6487    1.7498   -1.6362 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6472    1.0944   -2.3520 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1844    2.0145   -0.2487 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3059    2.8396   -0.2897 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208    0.6574    0.3570 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9781    0.7796    1.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383   -0.1455    0.3755 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5758   -1.4585    0.7269 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0460    1.7346    0.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4785    3.3564    1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1496    4.4218    3.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9928    2.8666    4.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4205    0.4636    2.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4942   -1.9871    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5615   -4.7553   -0.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6962   -4.4494   -2.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -4.1539   -4.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1064   -0.9266   -1.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4501    2.7066   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4686    1.6735   -2.2587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734    2.4367    0.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0362    2.5278    0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2591    0.1903   -0.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7170    0.1280    1.8268 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5857    0.3054    1.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591   -1.9467   -0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 26  1  0
 26 25  1  0
 25 33  1  0
 33 34  1  0
 33 31  1  0
 31 32  1  0
 31 29  1  0
 29 30  1  0
 25  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 29 27  1  0
 23  4  1  0
 13  6  1  0
 22 15  1  0
 28 46  1  0
 27 45  1  6
 25 44  1  6
 33 51  1  1
 34 52  1  0
 31 49  1  6
 32 50  1  0
 29 47  1  1
 30 48  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 21 43  1  0
  7 35  1  0
  8 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
M  END


  Mrv1652309052219032D          

 34 37  0  0  1  0            999 V2000
    0.7145   -2.8875    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
    0.0000   -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
    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
   -0.7145    2.0625    0.0000 O   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
    1.4289    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
    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
   -0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25  2  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0216908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(=O)OC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21(31)19-15(28)14(27)16(29)20(30)34-19/h1-5,14-16,19-20,22-25,27-30H/t14-,15-,16+,19-,20-/m0/s1

> <INCHI_KEY>
LOJXBHNAFUDMIQ-HGDKKCICSA-N

> <FORMULA>
C21H18O13

> <MOLECULAR_WEIGHT>
478.362

> <EXACT_MASS>
478.07474064

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.43887141762452

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

> <JCHEM_LOGP>
-0.3217932056666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.8620922714718935

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.361202198217491

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6863502780932738

> <JCHEM_POLAR_SURFACE_AREA>
223.66999999999996

> <JCHEM_REFRACTIVITY>
109.16079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  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  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6                                                       
CONECT   14    5   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22    4   24                                                  
CONECT   24   23                                                            
CONECT   25    2   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid	Generator

Chemical Formula

C₂₁H₁₈O₁₃

Average Mass

478.3620 Da

Monoisotopic Mass

478.07474 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

Traditional Name

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(=O)OC1=C(OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21(31)19-15(28)14(27)16(29)20(30)34-19/h1-5,14-16,19-20,22-25,27-30H/t14-,15-,16+,19-,20-/m0/s1

InChI Key

LOJXBHNAFUDMIQ-HGDKKCICSA-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
Anemone nemorosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
7-hydroxyflavonoid
Hydroxyflavonoid
Glucuronic acid or derivatives
Chromone
Benzopyran
1-benzopyran
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Pyranone
Oxane
Monosaccharide
Hydroxy acid
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxygen 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	-0.32	ChemAxon
pKa (Strongest Acidic)	6.36	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.16 m³·mol⁻¹	ChemAxon
Polarizability	43.44 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

15801288

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate (NP0216908)

MOL for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

3D MOL for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

3D SDF for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

3D-SDF for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

PDB for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

3D PDB for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

SMILES for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

INCHI for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

Structure for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)

3D Structure for NP0216908 (2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl (2s,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxane-2-carboxylate)