NP-MRD: Showing NP-Card for 5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid (NP0225400)

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Record Information

Version

2.0

Created at

2022-09-06 04:06:50 UTC

Updated at

2022-09-06 04:06:50 UTC

NP-MRD ID

NP0225400

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid

Description

Platyacanthin 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. 5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid is found in Rosa platyacantha. Based on a literature review very few articles have been published on Platyacanthin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206062D          

 47 50  0  0  1  0            999 V2000
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  1  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  2  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  1  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   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 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   -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   -2.8875    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
   -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 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
   -3.5724   -1.2375    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
   -3.5724   -2.8875    0.0000 C   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
   -4.2868   -4.1250    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
   -5.7158   -4.1250    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
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    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
   -2.8579   -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  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
  2 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
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 31 41  1  0  0  0  0
 41 42  1  0  0  0  0
 29 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 23 45  1  0  0  0  0
 45 46  1  0  0  0  0
 21 47  2  0  0  0  0
 15 47  1  0  0  0  0
M  END


  Mrv1652309062206062D          

 47 50  0  0  1  0            999 V2000
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  1  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  2  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  1  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   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 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   -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   -2.8875    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
   -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 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
   -3.5724   -1.2375    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
   -3.5724   -2.8875    0.0000 C   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
   -4.2868   -4.1250    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
   -5.7158   -4.1250    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
   -5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    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
   -2.8579   -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  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
  2 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
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 32 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 31 41  1  0  0  0  0
 41 42  1  0  0  0  0
 29 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 23 45  1  0  0  0  0
 45 46  1  0  0  0  0
 21 47  2  0  0  0  0
 15 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225400

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H](OC(=O)C2=CC(O)=C(O)C(OC3=C(C=C(OC4=C(C=C(O)C(O)=C4O)C(O)=O)C(O)=C3O)C(O)=O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O20/c28-5-13-17(34)18(35)21(38)27(46-13)47-26(43)6-1-9(29)14(31)11(2-6)44-23-8(25(41)42)4-12(16(33)20(23)37)45-22-7(24(39)40)3-10(30)15(32)19(22)36/h1-4,13,17-18,21,27-38H,5H2,(H,39,40)(H,41,42)/t13-,17-,18+,21-,27-/m1/s1

> <INCHI_KEY>
WHEUOVJKBVNNMT-RDJJNILTSA-N

> <FORMULA>
C27H24O20

> <MOLECULAR_WEIGHT>
668.469

> <EXACT_MASS>
668.086093173

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
58.007493856916774

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid

> <JCHEM_LOGP>
-0.24645643900000003

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.736854086797643

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1347855489063705

> <JCHEM_PKA_STRONGEST_BASIC>
-5.904176095569196

> <JCHEM_POLAR_SURFACE_AREA>
351.12

> <JCHEM_REFRACTIVITY>
146.60569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -13.337  -4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    4   14                                                  
CONECT   14   13                                                            
CONECT   15    2   16   47                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   47                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   45                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24   29                                                       
CONECT   29   28   30   43                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   41                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   32   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   31   42                                                  
CONECT   42   41                                                            
CONECT   43   29   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   23   46                                                  
CONECT   46   45                                                            
CONECT   47   21   15                                                       
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₄O₂₀

Average Mass

668.4690 Da

Monoisotopic Mass

668.08609 Da

IUPAC Name

5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid

Traditional Name

5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H](OC(=O)C2=CC(O)=C(O)C(OC3=C(C=C(OC4=C(C=C(O)C(O)=C4O)C(O)=O)C(O)=C3O)C(O)=O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H24O20/c28-5-13-17(34)18(35)21(38)27(46-13)47-26(43)6-1-9(29)14(31)11(2-6)44-23-8(25(41)42)4-12(16(33)20(23)37)45-22-7(24(39)40)3-10(30)15(32)19(22)36/h1-4,13,17-18,21,27-38H,5H2,(H,39,40)(H,41,42)/t13-,17-,18+,21-,27-/m1/s1

InChI Key

WHEUOVJKBVNNMT-RDJJNILTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rosa platyacantha	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
Diphenylether
Gallic acid or derivatives
Hexose monosaccharide
Gallic acid
Diaryl ether
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Hydroxybenzoic acid
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Tricarboxylic acid or derivatives
Benzoic acid
Benzoyl
Phenol ether
Catechol
Phenoxy compound
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Carboxylic acid
Ether
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	-0.25	ChemAxon
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	351.12 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	146.61 m³·mol⁻¹	ChemAxon
Polarizability	58.01 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	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

102273823

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid (NP0225400)

MOL for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

3D MOL for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

3D SDF for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

3D-SDF for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

PDB for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

3D PDB for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

SMILES for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

INCHI for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

Structure for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)

3D Structure for NP0225400 (5-(6-carboxy-2,3,4-trihydroxyphenoxy)-2-[2,3-dihydroxy-5-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}carbonyl)phenoxy]-3,4-dihydroxybenzoic acid)