NP-MRD: Showing NP-Card for (1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid (NP0195417)

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Record Information

Version

2.0

Created at

2022-09-04 13:16:30 UTC

Updated at

2022-09-04 13:16:30 UTC

NP-MRD ID

NP0195417

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

Description

3,4-Di-O-galloylquinic acid, also known as 3,4-dogqa, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1. (1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid is found in Quercus salicina. (1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid was first documented in 2011 (PMID: 21571480). Based on a literature review very few articles have been published on 3,4-Di-O-galloylquinic acid (PMID: 35842178).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215162D          

 35 37  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
    0.0000   -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  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
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8986   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -1.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -1.0678    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
    2.1434   -3.7125    0.0000 C   0  0  1  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
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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   -6.1875    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  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
    1.4289   -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
    1.4289   -6.6000    0.0000 C   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
   -0.7145   -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 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
   -2.8579   -6.6000    0.0000 O   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 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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  6  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 18 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 27 35  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -1.9261   -2.3064   -1.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4688   -1.2637   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5709   -0.3580   -0.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -0.5892   -0.1180 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3275   -0.5048    1.2945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2419    0.7175    1.9186 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7582    1.2309    2.7927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3475    0.2934    2.8225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3908   -0.2038    2.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    0.4228    4.1967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    1.7959    0.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0286    1.8562   -0.3257 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1248    2.7227   -0.2955 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5439    0.5418   -0.8416 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9057    0.4057   -0.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9267    0.1926   -1.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6424    0.1147   -2.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3191    0.0605   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6659    0.1419    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9806    0.0143    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3259    0.0981    2.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9585   -0.1959   -0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2945   -0.3308    0.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6295   -0.2823   -1.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6271   -0.4961   -2.4430 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3117   -0.1517   -1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9013   -1.0454   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7436   -1.9633   -1.3630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1345   -1.7715   -1.4236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9440   -2.7214   -2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6900   -0.6392   -0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0578   -0.3781   -0.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8416    0.2923   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4123    1.4439    0.2259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802    0.0826   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0429   -1.5644   -0.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -1.4095    1.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4507   -0.4044    1.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402    2.2010    2.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712    1.2090    4.7008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7519    1.7374    0.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4809    2.7846    1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6515    2.2614   -1.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0578    3.4625   -0.9206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4686    0.4492   -1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785    0.3078    1.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6279    0.2537    2.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5668   -0.2721    1.1743 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3680   -0.5557   -3.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0315   -0.2162   -2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3719   -2.8903   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9405   -2.6249   -2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7579   -0.9716   -1.3088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8194    2.1210    0.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8755    0.8530    0.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11  6  1  0
  6  7  1  1
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 33 35  2  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
  6  8  1  0
  8 10  1  0
  8  9  2  0
 14 12  1  0
 26 18  1  0
 35 27  1  0
 13 44  1  0
 12 43  1  6
 11 41  1  0
 11 42  1  0
  7 39  1  0
  5 37  1  0
  5 38  1  0
  4 36  1  6
 28 51  1  0
 30 52  1  0
 32 53  1  0
 34 54  1  0
 35 55  1  0
 14 45  1  6
 19 46  1  0
 21 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
 10 40  1  0
M  END


  Mrv1652309042215162D          

 35 37  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
    0.0000   -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  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
    1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8986   -1.8430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -1.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -1.0678    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
    2.1434   -3.7125    0.0000 C   0  0  1  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
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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   -6.1875    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  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
    1.4289   -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
    1.4289   -6.6000    0.0000 C   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
   -0.7145   -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 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
   -2.8579   -6.6000    0.0000 O   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 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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  6  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 18 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 27 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195417

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@](O)(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)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O14/c22-9-1-7(2-10(23)15(9)27)18(29)34-14-6-21(33,20(31)32)5-13(26)17(14)35-19(30)8-3-11(24)16(28)12(25)4-8/h1-4,13-14,17,22-28,33H,5-6H2,(H,31,32)/t13-,14-,17-,21+/m1/s1

> <INCHI_KEY>
SKUCQDOSGKINGP-YQMRLJPGSA-N

> <FORMULA>
C21H20O14

> <MOLECULAR_WEIGHT>
496.377

> <EXACT_MASS>
496.085305324

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.941994644686275

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
0.4739179346666669

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.803171537194004

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5523037999039566

> <JCHEM_PKA_STRONGEST_BASIC>
-4.024515121247577

> <JCHEM_POLAR_SURFACE_AREA>
251.73999999999995

> <JCHEM_REFRACTIVITY>
111.23459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,5R)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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       0.000  -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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.677  -3.440   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.657  -3.440   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.174  -3.708   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.131  -1.993   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   11                                             
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    4   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   18                                                       
CONECT   27    2   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   27                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
3,4-Di-O-galloylquinate	Generator
3,4-DOGQA	MeSH
3,4-Di-O-galloylquinic acid, 1R-(1alpha,2alpha,3beta,5alpha)-isomer	MeSH

Chemical Formula

C₂₁H₂₀O₁₄

Average Mass

496.3770 Da

Monoisotopic Mass

496.08531 Da

IUPAC Name

(1S,3R,4R,5R)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

Traditional Name

(1S,3R,4R,5R)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@](O)(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)C(O)=O

InChI Identifier

InChI=1S/C21H20O14/c22-9-1-7(2-10(23)15(9)27)18(29)34-14-6-21(33,20(31)32)5-13(26)17(14)35-19(30)8-3-11(24)16(28)12(25)4-8/h1-4,13-14,17,22-28,33H,5-6H2,(H,31,32)/t13-,14-,17-,21+/m1/s1

InChI Key

SKUCQDOSGKINGP-YQMRLJPGSA-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
Quercus salicina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Galloyl ester
Quinic acid
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Pyrogallol derivative
Benzenetriol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Phenol
Alpha-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	0.47	ChemAxon
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	251.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	111.23 m³·mol⁻¹	ChemAxon
Polarizability	43.94 Å³	ChemAxon
Number of Rings	3	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

405509

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

460895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sannomiya M, Rodrigues CM, Oliveira GCA, Carvalho JCS, da Costa LS, Spadari CC, Ferreira MJP, Vilegas W, Ishida K: Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity. J Ethnopharmacol. 2022 Oct 28;297:115534. doi: 10.1016/j.jep.2022.115534. Epub 2022 Jul 14. [PubMed:35842178 ]
Maldini M, Montoro P, Pizza C: Phenolic compounds from Byrsonima crassifolia L. bark: phytochemical investigation and quantitative analysis by LC-ESI MS/MS. J Pharm Biomed Anal. 2011 Aug 25;56(1):1-6. doi: 10.1016/j.jpba.2011.03.032. Epub 2011 Mar 29. [PubMed:21571480 ]
LOTUS database [Link]

Showing NP-Card for (1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid (NP0195417)

MOL for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D MOL for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D SDF for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D-SDF for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

PDB for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D PDB for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

SMILES for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

INCHI for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

Structure for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D Structure for NP0195417 ((1s,3r,4r,5r)-1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)