NP-MRD: Showing NP-Card for 2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate (NP0218609)

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Record Information

Version

2.0

Created at

2022-09-05 19:19:20 UTC

Updated at

2022-09-05 19:19:20 UTC

NP-MRD ID

NP0218609

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate

Description

2-[3,4-Dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate is found in Geum japonicum. 2-[3,4-Dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251508032D          

 54 58  0  0  0  0            999 V2000
    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  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
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  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
    3.5724   -3.7125    0.0000 C   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
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 15 26  2  0  0  0  0
  9 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 31 39  1  0  0  0  0
 27 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  2  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
 44 52  1  0  0  0  0
 40 53  1  0  0  0  0
  3 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END


  Mrv1533004251508032D          

 54 58  0  0  0  0            999 V2000
    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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  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
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  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
    3.5724   -3.7125    0.0000 C   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
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  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
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 15 26  2  0  0  0  0
  9 26  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 31 39  1  0  0  0  0
 27 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  2  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  2  0  0  0  0
 44 52  1  0  0  0  0
 40 53  1  0  0  0  0
  3 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218609

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(OC(=O)C2=CC(O)=C(O)C(OC3=CC=C(O)C(O)=C3O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H28O21/c34-9-21-27(46)28(52-30(47)10-3-14(36)22(41)15(37)4-10)29(53-31(48)11-5-16(38)23(42)17(39)6-11)33(51-21)54-32(49)12-7-18(40)24(43)20(8-12)50-19-2-1-13(35)25(44)26(19)45/h1-8,21,27-29,33-46H,9H2

> <INCHI_KEY>
RHKFRJASWOWCCU-UHFFFAOYSA-N

> <FORMULA>
C33H28O21

> <MOLECULAR_WEIGHT>
760.566

> <EXACT_MASS>
760.112307922

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
69.54383178467296

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl 3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoate

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.714428972666666

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.816764661978997

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.933679977210318

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548940931350864

> <JCHEM_POLAR_SURFACE_AREA>
360.35

> <JCHEM_REFRACTIVITY>
173.42010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl 3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+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       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   53                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   26                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24                                                            
CONECT   26   15    9                                                       
CONECT   27    5   28   40                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   31                                                       
CONECT   40   27   41   53                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   52                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   44                                                       
CONECT   53   40    3   54                                                  
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  116    0
END

View in JSmol

Synonyms

Value	Source
2-[3,4-Dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₃₃H₂₈O₂₁

Average Mass

760.5660 Da

Monoisotopic Mass

760.11231 Da

IUPAC Name

5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl 3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoate

Traditional Name

5-hydroxy-6-(hydroxymethyl)-3,4-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl 3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(OC(=O)C2=CC(O)=C(O)C(OC3=CC=C(O)C(O)=C3O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C1O

InChI Identifier

InChI=1S/C33H28O21/c34-9-21-27(46)28(52-30(47)10-3-14(36)22(41)15(37)4-10)29(53-31(48)11-5-16(38)23(42)17(39)6-11)33(51-21)54-32(49)12-7-18(40)24(43)20(8-12)50-19-2-1-13(35)25(44)26(19)45/h1-8,21,27-29,33-46H,9H2

InChI Key

RHKFRJASWOWCCU-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
Geum japonicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Galloyl ester
Diphenylether
Gallic acid or derivatives
P-hydroxybenzoic acid ester
Diaryl ether
Dihydroxybenzoic acid
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid alkyl ester
Benzoate ester
5-unsubstituted pyrrogallol
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Tricarboxylic acid or derivatives
Benzoyl
Catechol
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Secondary alcohol
Carboxylic acid ester
Polyol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organic oxide
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.62	ALOGPS
logP	2.71	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	5.93	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	360.35 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	173.42 m³·mol⁻¹	ChemAxon
Polarizability	69.54 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

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

85067422

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-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate (NP0218609)

MOL for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

PDB for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

Structure for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0218609 (2-[3,4-dihydroxy-5-(2,3,4-trihydroxyphenoxy)benzoyloxy]-5-hydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyloxy)oxan-4-yl 3,4,5-trihydroxybenzoate)