NP-MRD: Showing NP-Card for (1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid (NP0225558)

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Record Information

Version

2.0

Created at

2022-09-06 04:18:49 UTC

Updated at

2022-09-06 04:18:49 UTC

NP-MRD ID

NP0225558

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

Description

1,3,4-Tri-O-galloylquinic acid belongs to the class of organic compounds known as o-galloylquinic acids and derivatives. O-galloylquinic acids and derivatives are compounds containing a galloic acid moiety, linked to one hydroxyl group of a quinic acid moiety. (1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid is found in Castanopsis fissa. (1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid was first documented in 1990 (PMID: 1698933). Based on a literature review very few articles have been published on 1,3,4-Tri-O-galloylquinic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206182D          

 46 49  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
    1.4289   -4.9500    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  2  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
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5303   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249   -2.7615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731   -1.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5909   -0.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390    0.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9337   -0.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640    0.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158   -0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0283   -1.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -1.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -1.0678    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
   -0.7145   -3.7125    0.0000 C   0  0  1  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
    0.0000   -4.1250    0.0000 C   0  0  1  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   -5.3625    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   -6.1875    0.0000 C   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
    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
   -0.7145   -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
   -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
   -1.4289   -6.6000    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
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    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
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 10 18  1  0  0  0  0
  6 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 29 37  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
 38 46  1  0  0  0  0
M  END


  Mrv1652309062206182D          

 46 49  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
    1.4289   -4.9500    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  2  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
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5303   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249   -2.7615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8731   -1.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5909   -0.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8390    0.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9337   -0.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4640    0.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2158   -0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0283   -1.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6855   -1.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428   -1.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -1.0678    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
   -0.7145   -3.7125    0.0000 C   0  0  1  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
    0.0000   -4.1250    0.0000 C   0  0  1  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   -5.3625    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   -6.1875    0.0000 C   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
    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
   -0.7145   -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
   -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
   -1.4289   -6.6000    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
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    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
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 10 18  1  0  0  0  0
  6 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 29 37  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  2  0  0  0  0
 38 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225558

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@@](C[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)(OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H24O18/c29-12-1-9(2-13(30)20(12)36)24(39)44-19-8-28(27(42)43,46-26(41)11-5-16(33)22(38)17(34)6-11)7-18(35)23(19)45-25(40)10-3-14(31)21(37)15(32)4-10/h1-6,18-19,23,29-38H,7-8H2,(H,42,43)/t18-,19-,23-,28+/m1/s1

> <INCHI_KEY>
MFFWGSMFANTCDY-LGFATHPOSA-N

> <FORMULA>
C28H24O18

> <MOLECULAR_WEIGHT>
648.482

> <EXACT_MASS>
648.096263933

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.86394388383784

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4R,5R)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

> <JCHEM_LOGP>
2.0585218183333325

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.643784935407705

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4270694831387587

> <JCHEM_PKA_STRONGEST_BASIC>
-5.5489400233592585

> <JCHEM_POLAR_SURFACE_AREA>
318.5

> <JCHEM_REFRACTIVITY>
146.99929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,5R)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic 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       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.990  -3.440   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.506  -3.708   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.033  -5.155   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.496  -2.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.970  -1.081   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.960   0.099   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.433   1.546   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.476  -0.169   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.466   1.011   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.003  -1.616   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.519  -1.883   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.013  -2.795   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.990  -3.440   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.506  -3.708   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.463  -1.993   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.334 -10.010   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 -11.550   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   19   22                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   10                                                       
CONECT   19    6   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    6   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    4   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   29                                                       
CONECT   38    2   39   46                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   38                                                       
MASTER        0    0    0    0    0    0    0    0   46    0   98    0
END

View in JSmol

Synonyms

Value	Source
1,3,4-Tri-O-galloylquinate	Generator

Chemical Formula

C₂₈H₂₄O₁₈

Average Mass

648.4820 Da

Monoisotopic Mass

648.09626 Da

IUPAC Name

(1S,3R,4R,5R)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

Traditional Name

(1S,3R,4R,5R)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@](C[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1)(OC(=O)C1=CC(O)=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C28H24O18/c29-12-1-9(2-13(30)20(12)36)24(39)44-19-8-28(27(42)43,46-26(41)11-5-16(33)22(38)17(34)6-11)7-18(35)23(19)45-25(40)10-3-14(31)21(37)15(32)4-10/h1-6,18-19,23,29-38H,7-8H2,(H,42,43)/t18-,19-,23-,28+/m1/s1

InChI Key

MFFWGSMFANTCDY-LGFATHPOSA-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
Castanopsis fissa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-galloylquinic acids and derivatives. O-galloylquinic acids and derivatives are compounds containing a galloic acid moiety, linked to one hydroxyl group of a quinic acid moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

O-galloylquinic acids and derivatives

Alternative Parents

Substituents

1-o-galloylquinic-acid
Galloyl ester
Tetracarboxylic acid or derivatives
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	2.06	ChemAxon
pKa (Strongest Acidic)	2.43	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	318.5 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	147 m³·mol⁻¹	ChemAxon
Polarizability	57.86 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

398344

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

452237

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nonaka G, Nishioka I, Nishizawa M, Yamagishi T, Kashiwada Y, Dutschman GE, Bodner AJ, Kilkuskie RE, Cheng YC, Lee KH: Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells. J Nat Prod. 1990 May-Jun;53(3):587-95. doi: 10.1021/np50069a008. [PubMed:1698933 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid (NP0225558)

MOL for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D MOL for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D SDF for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D-SDF for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

PDB for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D PDB for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

SMILES for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

INCHI for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

Structure for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D Structure for NP0225558 ((1s,3r,4r,5r)-3-hydroxy-1,4,5-tris(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)