NP-MRD: Showing NP-Card for sanguisorbic acid (NP0186565)

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Record Information

Version

2.0

Created at

2022-09-04 02:27:37 UTC

Updated at

2022-09-04 02:27:38 UTC

NP-MRD ID

NP0186565

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sanguisorbic acid

Description

3-(5-Carboxy-2,3-dihydroxyphenoxy)-4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. sanguisorbic acid is found in Epilobium hirsutum. 3-(5-Carboxy-2,3-dihydroxyphenoxy)-4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171523342D          

 36 38  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   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
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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 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
   -3.5724   -5.3625    0.0000 C   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
   -2.8579   -6.6000    0.0000 O   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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6657   -6.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -5.3802   -3.3713    0.0000 O   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 20 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  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 10 36  2  0  0  0  0
  4 36  1  0  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    3.0613    2.5797   -1.7639 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9643    2.3212   -0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0308    3.1945   -0.8388 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8960    1.1465   -0.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9045    0.9087    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8400   -0.2158    1.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8687   -0.4151    2.5353 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7824   -1.0937    1.5763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253   -2.2103    2.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7595   -0.8532    0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7165   -1.7446    0.6104 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6574   -1.5849   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714   -2.1682   -1.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9457   -2.8805   -1.8366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2685   -2.0151   -2.3937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340   -2.5614   -3.6605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4169   -1.2931   -2.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4596   -1.1518   -2.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5282   -0.7201   -0.7891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880    0.0317   -0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002    1.4030   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7152    2.1153   -1.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6810    1.5346   -1.6007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8281    3.4817   -1.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9218    2.0823   -0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539    1.4452    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0694    2.1287    0.8834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8801    0.0705    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9246   -0.5869    1.3007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7726   -0.5883    0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6459   -1.9644    0.4522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4755   -0.8812    0.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5598   -0.2897    1.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0364   -0.8896    2.3821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0937    1.0037    1.5758 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8387    0.2522   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9802    2.8699   -0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7556    1.5611    0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9899   -1.1550    3.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4453   -2.4050    3.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -3.3250   -2.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5609   -3.0798   -3.9576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2729   -0.6301   -2.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1693    4.1288   -0.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568    3.1612   -0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8382    1.6546    1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9846   -1.5652    1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3372   -2.5424    0.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8633    1.2460    1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571    0.4894   -0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 32  2  0
 32 33  1  0
 33 35  1  0
 33 34  2  0
 19 20  1  0
 20 30  2  0
 30 31  1  0
 30 28  1  0
 28 29  1  0
 28 26  2  0
 26 27  1  0
 26 25  1  0
 25 21  2  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 10 36  2  0
 36  4  1  0
 32 12  1  0
 21 20  1  0
  3 37  1  0
  5 38  1  0
  7 39  1  0
  9 40  1  0
 14 41  1  0
 16 42  1  0
 18 43  1  0
 35 49  1  0
 31 48  1  0
 29 47  1  0
 27 46  1  0
 25 45  1  0
 24 44  1  0
 36 50  1  0
M  END


  Mrv1533004171523342D          

 36 38  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 O   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
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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 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
   -3.5724   -5.3625    0.0000 C   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
   -2.8579   -6.6000    0.0000 O   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
   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6657   -6.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -5.3802   -3.3713    0.0000 O   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  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 20  1  0  0  0  0
 20 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  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 10 36  2  0  0  0  0
  4 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0186565

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(O)=C(O)C(OC2=C(O)C(O)=C(O)C(=C2C(O)=O)C2=C(O)C(O)=C(O)C=C2C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H14O15/c22-6-1-4(19(30)31)2-8(12(6)24)36-18-11(21(34)35)10(15(27)16(28)17(18)29)9-5(20(32)33)3-7(23)13(25)14(9)26/h1-3,22-29H,(H,30,31)(H,32,33)(H,34,35)

> <INCHI_KEY>
IGSQOFHPQLBLHF-UHFFFAOYSA-N

> <FORMULA>
C21H14O15

> <MOLECULAR_WEIGHT>
506.328

> <EXACT_MASS>
506.033269751

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
43.37258849970684

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(6-carboxy-2,3,4-trihydroxyphenyl)-6-(5-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoic acid

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
1.6649845116666664

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
3.490580415497403

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.821259019528653

> <JCHEM_PKA_STRONGEST_BASIC>
-6.175402169583799

> <JCHEM_POLAR_SURFACE_AREA>
282.96999999999997

> <JCHEM_REFRACTIVITY>
115.05079999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(6-carboxy-2,3,4-trihydroxyphenyl)-6-(5-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -4.620   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       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.336  -6.930   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      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -8.709 -12.957   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -10.043  -6.293   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   36                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
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   20   24                                                  
CONECT   20   19   12   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   32                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   24   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-(5-Carboxy-2,3-dihydroxyphenoxy)-4,4',5,5',6,6'-hexahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylate	Generator

Chemical Formula

C₂₁H₁₄O₁₅

Average Mass

506.3280 Da

Monoisotopic Mass

506.03327 Da

IUPAC Name

2-(6-carboxy-2,3,4-trihydroxyphenyl)-6-(5-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoic acid

Traditional Name

2-(6-carboxy-2,3,4-trihydroxyphenyl)-6-(5-carboxy-2,3-dihydroxyphenoxy)-3,4,5-trihydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(O)=C(O)C(OC2=C(O)C(O)=C(O)C(=C2C(O)=O)C2=C(O)C(O)=C(O)C=C2C(O)=O)=C1

InChI Identifier

InChI=1S/C21H14O15/c22-6-1-4(19(30)31)2-8(12(6)24)36-18-11(21(34)35)10(15(27)16(28)17(18)29)9-5(20(32)33)3-7(23)13(25)14(9)26/h1-3,22-29H,(H,30,31)(H,32,33)(H,34,35)

InChI Key

IGSQOFHPQLBLHF-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
Epilobium hirsutum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Biphenol
Diphenylether
Biphenyl
Gallic acid or derivatives
Gallic acid
Diaryl ether
Dihydroxybenzoic acid
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzenetriol
Pyrogallol derivative
Benzoyl
Phenoxy compound
Catechol
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Polyol
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	2.79	ALOGPS
logP	1.66	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.82	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	282.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.05 m³·mol⁻¹	ChemAxon
Polarizability	43.37 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	No	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

71308268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for sanguisorbic acid (NP0186565)

MOL for NP0186565 (sanguisorbic acid)

3D MOL for NP0186565 (sanguisorbic acid)

3D SDF for NP0186565 (sanguisorbic acid)

3D-SDF for NP0186565 (sanguisorbic acid)

PDB for NP0186565 (sanguisorbic acid)

3D PDB for NP0186565 (sanguisorbic acid)

SMILES for NP0186565 (sanguisorbic acid)

INCHI for NP0186565 (sanguisorbic acid)

Structure for NP0186565 (sanguisorbic acid)

3D Structure for NP0186565 (sanguisorbic acid)