NP-MRD: Showing NP-Card for 4-O-Digalloyl-3,5-di-O-galloylquinic acid (NP0338481)

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Record Information

Version

2.0

Created at

2024-09-11 15:40:49 UTC

Updated at

2024-09-11 15:40:50 UTC

NP-MRD ID

NP0338481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-O-Digalloyl-3,5-di-O-galloylquinic acid

Description

4-O-Digalloyl-3,5-di-O-galloylquinic acid, also known as 3,5,4,4-tetragqa or 3,5-g-4-digqa, belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). 4-O-Digalloyl-3,5-di-O-galloylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221102D          

 57 61  0  0  1  0            999 V2000
   -0.2033   -9.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5574   -9.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0700   -8.6567    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
    0.0000   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8820   -7.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230   -7.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8922   -7.9906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689   -8.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026   -9.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5390   -9.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726  -10.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417  -10.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5781  -10.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080   -9.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107   -9.7240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716   -8.7432    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
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031   -5.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860   -5.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706   -4.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597   -5.3667    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
    1.4289   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2380   -7.7502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9394   -7.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -6.4995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490   -7.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9783   -8.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7550   -7.8146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309   -8.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4602   -9.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -9.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -9.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -8.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589  -11.1805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224  -12.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662  -12.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866  -12.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748  -15.2806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392  -16.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7562  -15.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961  -11.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  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
 15 17  2  0  0  0  0
  9 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  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
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 46 54  1  0  0  0  0
 42 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 38 57  1  0  0  0  0
M  END


  Mrv0541 02241221102D          

 57 61  0  0  1  0            999 V2000
   -0.2033   -9.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5574   -9.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0700   -8.6567    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
    0.0000   -7.4250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8820   -7.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230   -7.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8922   -7.9906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8689   -8.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026   -9.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5390   -9.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9726  -10.5429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3417  -10.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5781  -10.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9080   -9.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107   -9.7240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6716   -8.7432    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
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3031   -5.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860   -5.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2706   -4.6340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597   -5.3667    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
    1.4289   -7.4250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2380   -7.7502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9394   -7.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -6.4995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490   -7.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9783   -8.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7550   -7.8146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8309   -8.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4602   -9.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -9.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9068   -9.9945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -8.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589  -11.1805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224  -12.3768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7662  -12.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866  -12.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748  -15.2806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6392  -16.1262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7562  -15.2866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961  -11.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145  -10.3125    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  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
 15 17  2  0  0  0  0
  9 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  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
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 46 54  1  0  0  0  0
 42 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  2  0  0  0  0
 38 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1(O)C[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)=C2)[C@@H](C1)OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H28O22/c36-15-1-11(2-16(37)25(15)44)30(47)54-23-9-35(53,34(51)52)10-24(55-31(48)12-3-17(38)26(45)18(39)4-12)29(23)57-33(50)14-7-21(42)28(22(43)8-14)56-32(49)13-5-19(40)27(46)20(41)6-13/h1-8,23-24,29,36-46,53H,9-10H2,(H,51,52)/t23-,24-,29?,35?/m1/s1

> <INCHI_KEY>
IUPQNOUMMBZOED-JHZIIMIVSA-N

> <FORMULA>
C35H28O22

> <MOLECULAR_WEIGHT>
800.5836

> <EXACT_MASS>
800.10722258

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
72.18316113625937

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,5R)-4-[3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-1-hydroxy-3,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
4.412826587666666

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.6398197641124295

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.355508412439931

> <JCHEM_PKA_STRONGEST_BASIC>
-3.607386877635217

> <JCHEM_POLAR_SURFACE_AREA>
385.26000000000005

> <JCHEM_REFRACTIVITY>
182.76399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5R)-4-[3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-1-hydroxy-3,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.379 -16.885   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.040 -17.238   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.997 -16.159   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.646 -13.482   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.030 -14.430   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.665 -14.916   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -3.489 -15.965   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.432 -17.085   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.873 -18.560   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.816 -19.680   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.371 -18.916   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.812 -20.391   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -5.428 -17.796   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.927 -18.151   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.987 -16.321   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.432 -10.401   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.347 -10.235   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.505  -8.650   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.231 -10.018   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.178 -14.467   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.487 -13.628   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.917 -12.132   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.118 -14.111   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.293 -15.107   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.743 -14.587   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.018 -16.622   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.192 -17.618   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.568 -17.141   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.293 -18.656   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.393 -16.145   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000 -18.480   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.910 -20.870   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.000 -21.560   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -0.042 -23.103   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.430 -23.816   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.962 -23.723   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.334 -25.410   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       2.667 -27.720   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.060 -28.524   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       1.334 -28.490   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       1.193 -30.102   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       0.000 -27.720   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -1.412 -28.535   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       0.000 -26.180   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -1.334 -20.790   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -2.793 -21.340   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -1.334 -19.250   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   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9                                                       
CONECT   18    5   19                                                       
CONECT   19   18   20   21   24                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25                                                       
CONECT   25   24    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   57                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   55                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   54                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   46                                                       
CONECT   55   42   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   38                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

View in JSmol

Synonyms

Value	Source
4-O-Digalloyl-3,5-di-O-galloylquinate	Generator
3,5,4,4-Tetragqa	HMDB
3,5-Di-galloyl-4-O-digalloylquinic acid	HMDB
3,5-Di-O-galloyl-4-O-digalloylquinic acid	HMDB
3,5-g-4-DiGQA	HMDB
(3R,5R)-4-[3,5-Dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-1-hydroxy-3,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylate	Generator

Chemical Formula

C₃₅H₂₈O₂₂

Average Mass

800.5836 Da

Monoisotopic Mass

800.10722 Da

IUPAC Name

(3R,5R)-4-[3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-1-hydroxy-3,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

Traditional Name

(3R,5R)-4-[3,5-dihydroxy-4-(3,4,5-trihydroxybenzoyloxy)benzoyloxy]-1-hydroxy-3,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1(O)C[C@@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C2=CC(O)=C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)=C2)[C@@H](C1)OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C35H28O22/c36-15-1-11(2-16(37)25(15)44)30(47)54-23-9-35(53,34(51)52)10-24(55-31(48)12-3-17(38)26(45)18(39)4-12)29(23)57-33(50)14-7-21(42)28(22(43)8-14)56-32(49)13-5-19(40)27(46)20(41)6-13/h1-8,23-24,29,36-46,53H,9-10H2,(H,51,52)/t23-,24-,29?,35?/m1/s1

InChI Key

IUPQNOUMMBZOED-JHZIIMIVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
Pentacarboxylic acid or derivatives
Galloyl ester
Quinic acid
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Phenol ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Phenoxy compound
Benzoyl
Resorcinol
Phenol
1-hydroxy-4-unsubstituted benzenoid
Cyclohexanol
1-hydroxy-2-unsubstituted benzenoid
Alpha-hydroxy acid
Cyclitol or derivatives
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
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	2.64	ALOGPS
logP	4.41	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.36	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	385.26 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	182.76 m³·mol⁻¹	ChemAxon
Polarizability	72.18 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

HMDB0039346

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-O-Digalloyl-3,5-di-O-galloylquinic acid (NP0338481)

MOL for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

3D MOL for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

3D SDF for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

3D-SDF for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

PDB for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

3D PDB for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

SMILES for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

INCHI for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

Structure for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)

3D Structure for NP0338481 (4-O-Digalloyl-3,5-di-O-galloylquinic acid)