NP-MRD: Showing NP-Card for 1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid (NP0318832)

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Record Information

Version

2.0

Created at

2022-09-11 19:33:24 UTC

Updated at

2022-09-11 19:33:25 UTC

NP-MRD ID

NP0318832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

1,3-Dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid 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. 1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid is found in Castanopsis fissa, Platycarya strobilacea and Quercus salicina. 1,3-Dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191516382D          

 35 37  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -1.8430    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  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 11 19  1  0  0  0  0
  7 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 24 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    2.0686   -0.9089    1.9756 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0484   -0.1535    0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415   -0.6682   -0.1729 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714   -1.9383   -0.2627 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5594   -2.7533   -1.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096   -4.1272   -1.4713 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5495   -4.9161   -0.4591 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237   -4.6587   -2.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1480   -5.6671   -2.9023 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -4.0312   -3.9829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4893   -4.2048   -1.4272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -3.3212   -0.3970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4844   -3.3916   -0.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5900   -1.8999   -0.6548 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3217   -0.9415    0.0291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0257    0.0073   -0.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9576   -0.0586   -1.9616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8181    1.0476   -0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4834    1.9462   -0.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2662    2.9750   -0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9048    3.8395   -1.1798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3953    3.1201    1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1510    4.1119    1.6426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7101    2.1950    1.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8412    2.3421    3.2267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471    1.1925    1.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304    1.1792    1.0167 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087    1.6048    2.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7755    2.8550    2.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3608    3.2871    3.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689    3.7054    1.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453    4.9545    1.3426 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1856    3.2622    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874    4.1390   -1.0478 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160    2.0074   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9338   -2.5345    0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886   -2.2206   -2.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -2.7969   -1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -4.4101    0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5942   -3.8882   -4.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9316   -3.9503   -2.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7558   -5.2582   -1.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7296   -3.6035    0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8522   -3.6526    0.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6749   -1.7658   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003    1.8570   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4765    4.5923   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6586    4.7960    1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3679    1.7019    3.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4283    0.4912    1.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2513    0.9850    3.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3844    2.7006    4.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7586    5.2448    2.1969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7694    3.8653   -1.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1663    1.7146   -1.0209 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  1
 11 41  1  0
 11 42  1  0
  7 39  1  0
  5 37  1  0
  5 38  1  0
  4 36  1  1
 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


  Mrv1533004191516382D          

 35 37  0  0  0  0            999 V2000
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986   -1.8430    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  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 11 19  1  0  0  0  0
  7 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 24 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC(O)(CC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C1OC(=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)

> <INCHI_KEY>
SKUCQDOSGKINGP-UHFFFAOYSA-N

> <FORMULA>
C21H20O14

> <MOLECULAR_WEIGHT>
496.377

> <EXACT_MASS>
496.085305324

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.718975326477945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
0.4739179346666669

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.803171537194004

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.552303799903953

> <JCHEM_PKA_STRONGEST_BASIC>
-4.024515121247577

> <JCHEM_POLAR_SURFACE_AREA>
251.73999999999995

> <JCHEM_REFRACTIVITY>
111.23459999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.52e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.677  -3.440   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.657  -3.440   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.174  -3.708   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.131  -1.993   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   33                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11                                                       
CONECT   20    7    2   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   24                                                       
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
1,3-Dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylate	Generator

Chemical Formula

C₂₁H₂₀O₁₄

Average Mass

496.3770 Da

Monoisotopic Mass

496.08531 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1CC(O)(CC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C1OC(=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)

InChI Key

SKUCQDOSGKINGP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Castanopsis fissa	LOTUS Database	35616633
Platycarya strobilacea	LOTUS Database	35616633
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	1.11	ALOGPS
logP	0.47	ChemAxon
logS	-2.5	ALOGPS
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	43.72 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

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

13270011

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid (NP0318832)

MOL for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D MOL for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D SDF for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D-SDF for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

PDB for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D PDB for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

SMILES for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

INCHI for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

Structure for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)

3D Structure for NP0318832 (1,3-dihydroxy-4,5-bis(3,4,5-trihydroxybenzoyloxy)cyclohexane-1-carboxylic acid)