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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:56:49 UTC

Update Date

2021-09-26 22:52:48 UTC

HMDB ID

HMDB0244815

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,3,6-Tri-O-galloyl-beta-D-glucose

Description

[3,5-dihydroxy-4,6-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). Based on a literature review very few articles have been published on [3,5-dihydroxy-4,6-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,3,6-tri-o-galloyl-beta-d-glucose is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,3,6-Tri-O-galloyl-beta-D-glucose is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1533004241500522D          

 45 48  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 O   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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    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
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    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
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    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
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 22 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
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 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 37 45  1  0  0  0  0
M  END

HMDB0244815
     RDKit          3D
1,3,6-Tri-O-galloyl-beta-D-glucose
 69 72  0  0  0  0  0  0  0  0999 V2000
    2.8626    0.4658   -3.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    0.4916   -1.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    0.9364   -0.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    1.3894   -1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.3787   -1.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104    0.9426   -2.0998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    1.1772   -1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7306    2.4364   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722    3.4322   -0.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7435    3.1934   -1.1425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650    4.7637    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883    5.1073    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    6.3628    1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0730    7.3215    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573    8.5679    1.6827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2539    6.9830    0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0590    0.0671   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2366    0.3219    1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4711   -1.1759   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2435   -3.3834   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033   -3.4699   -1.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0666   -5.6694    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2499   -6.7628    1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9111   -7.9097    0.6340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7656   -6.7153    2.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6060   -5.4658    4.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402   -4.4858    1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -0.8335   -0.9486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6182   -1.9009   -1.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4833    0.0290   -1.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -0.4227   -2.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6244   -0.8562   -1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5335   -1.3124   -2.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9563   -0.8340   -0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1966   -1.2680   -0.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4226   -0.3697    1.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5116    1.9121   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2516   -7.9069   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7240   -6.2504    4.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296   -3.5748    2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4930   -0.6351    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038   -2.2432   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1240   -0.4407   -3.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2877   -1.3254   -3.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8495   -1.5962   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -0.0321    2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    0.4075    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
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  9 10  2  0
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 13 15  2  0
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  7 20  1  0
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 35  5  1  0
 45 37  1  0
 19 11  1  0
 34 26  1  0
  4 46  1  0
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  5 48  1  0
  7 49  1  0
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 35 63  1  0
 36 64  1  0
 38 65  1  0
 40 66  1  0
 42 67  1  0
 44 68  1  0
 45 69  1  0
M  END


  Mrv1533004241500522D          

 45 48  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 O   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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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
   -0.7145   -3.7125    0.0000 O   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
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    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
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 22 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  2  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 37 45  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244815

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)23(44-25(40)9-3-13(30)19(35)14(31)4-9)22(38)27(43-17)45-26(41)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-38H,7H2

> <INCHI_KEY>
RNKMOGIPOMVCHO-UHFFFAOYSA-N

> <FORMULA>
C27H24O18

> <MOLECULAR_WEIGHT>
636.471

> <EXACT_MASS>
636.096263933

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
59.07878496798944

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3,5-dihydroxy-4,6-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.821272432999999

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.105931898288329

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.628542426447977

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548902248577655

> <JCHEM_POLAR_SURFACE_AREA>
310.66

> <JCHEM_REFRACTIVITY>
143.2175

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tannic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244815
     RDKit          3D
1,3,6-Tri-O-galloyl-beta-D-glucose
 69 72  0  0  0  0  0  0  0  0999 V2000
    2.8626    0.4658   -3.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    0.4916   -1.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    0.9364   -0.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    1.3894   -1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.3787   -1.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104    0.9426   -2.0998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    1.1772   -1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7306    2.4364   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722    3.4322   -0.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7435    3.1934   -1.1425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650    4.7637    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883    5.1073    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    6.3628    1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049    6.6978    1.8694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0730    7.3215    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573    8.5679    1.6827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2539    6.9830    0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355    7.9659    0.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4315    5.7308   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    0.0671   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2366    0.3219    1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4711   -1.1759   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968   -2.2225    0.1810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -3.3834   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033   -3.4699   -1.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204   -4.5242    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0666   -5.6694    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2499   -6.7628    1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9111   -7.9097    0.6340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7656   -6.7153    2.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9248   -7.7901    3.2391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -5.5690    2.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060   -5.4658    4.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402   -4.4858    1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -0.8335   -0.9486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6182   -1.9009   -1.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4833    0.0290   -1.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -0.4227   -2.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6244   -0.8562   -1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5335   -1.3124   -2.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9563   -0.8340   -0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1966   -1.2680   -0.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567   -0.3808    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4226   -0.3697    1.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8252    0.0461   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5116    1.9121   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331    2.2186   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139    0.0741   -2.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    1.2446   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157    4.3536    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    5.9855    1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148    9.2546    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1041    7.7269   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3591    5.5074   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1067   -0.1300    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123   -0.3065    1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281   -1.4328   -1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4418   -5.6852   -0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2516   -7.9069   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039   -8.6123    2.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -6.2504    4.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296   -3.5748    2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4930   -0.6351    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038   -2.2432   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1240   -0.4407   -3.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2877   -1.3254   -3.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8495   -1.5962   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -0.0321    2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    0.4075    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
  7 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  2  0
 22 35  1  0
 35 36  1  0
  2 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43 45  2  0
 35  5  1  0
 45 37  1  0
 19 11  1  0
 34 26  1  0
  4 46  1  0
  4 47  1  0
  5 48  1  0
  7 49  1  0
 12 50  1  0
 14 51  1  0
 16 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 21 56  1  0
 22 57  1  0
 27 58  1  0
 29 59  1  0
 31 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
 36 64  1  0
 38 65  1  0
 40 66  1  0
 42 67  1  0
 44 68  1  0
 45 69  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
CONECT   17    3   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   22                                                       
CONECT   31   18   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    2   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   45                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   37                                                       
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

COMPND    HMDB0244815
HETATM    1  O1  UNL     1       2.863   0.466  -3.064  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.150   0.492  -1.844  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.276   0.936  -0.879  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.000   1.389  -1.196  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.101   0.379  -1.849  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.110   0.943  -2.100  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.981   1.177  -1.098  1.00  0.00           C  
HETATM    8  O4  UNL     1      -1.731   2.436  -0.522  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.672   3.432  -0.575  1.00  0.00           C  
HETATM   10  O5  UNL     1      -3.743   3.193  -1.142  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.465   4.764   0.009  1.00  0.00           C  
HETATM   12  C7  UNL     1      -1.288   5.107   0.661  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.090   6.363   1.212  1.00  0.00           C  
HETATM   14  O6  UNL     1       0.105   6.698   1.869  1.00  0.00           O  
HETATM   15  C9  UNL     1      -2.073   7.321   1.127  1.00  0.00           C  
HETATM   16  O7  UNL     1      -1.857   8.568   1.683  1.00  0.00           O  
HETATM   17  C10 UNL     1      -3.254   6.983   0.475  1.00  0.00           C  
HETATM   18  O8  UNL     1      -4.236   7.966   0.399  1.00  0.00           O  
HETATM   19  C11 UNL     1      -3.431   5.731  -0.066  1.00  0.00           C  
HETATM   20  C12 UNL     1      -2.059   0.067  -0.119  1.00  0.00           C  
HETATM   21  O9  UNL     1      -1.237   0.322   1.013  1.00  0.00           O  
HETATM   22  C13 UNL     1      -1.471  -1.176  -0.740  1.00  0.00           C  
HETATM   23  O10 UNL     1      -1.597  -2.223   0.181  1.00  0.00           O  
HETATM   24  C14 UNL     1      -2.244  -3.383  -0.213  1.00  0.00           C  
HETATM   25  O11 UNL     1      -2.703  -3.470  -1.390  1.00  0.00           O  
HETATM   26  C15 UNL     1      -2.420  -4.524   0.679  1.00  0.00           C  
HETATM   27  C16 UNL     1      -3.067  -5.669   0.268  1.00  0.00           C  
HETATM   28  C17 UNL     1      -3.250  -6.763   1.085  1.00  0.00           C  
HETATM   29  O12 UNL     1      -3.911  -7.910   0.634  1.00  0.00           O  
HETATM   30  C18 UNL     1      -2.766  -6.715   2.378  1.00  0.00           C  
HETATM   31  O13 UNL     1      -2.925  -7.790   3.239  1.00  0.00           O  
HETATM   32  C19 UNL     1      -2.110  -5.569   2.813  1.00  0.00           C  
HETATM   33  O14 UNL     1      -1.606  -5.466   4.094  1.00  0.00           O  
HETATM   34  C20 UNL     1      -1.940  -4.486   1.972  1.00  0.00           C  
HETATM   35  C21 UNL     1       0.005  -0.834  -0.949  1.00  0.00           C  
HETATM   36  O15 UNL     1       0.618  -1.901  -1.578  1.00  0.00           O  
HETATM   37  C22 UNL     1       4.483   0.029  -1.392  1.00  0.00           C  
HETATM   38  C23 UNL     1       5.386  -0.423  -2.326  1.00  0.00           C  
HETATM   39  C24 UNL     1       6.624  -0.856  -1.942  1.00  0.00           C  
HETATM   40  O16 UNL     1       7.533  -1.312  -2.894  1.00  0.00           O  
HETATM   41  C25 UNL     1       6.956  -0.834  -0.599  1.00  0.00           C  
HETATM   42  O17 UNL     1       8.197  -1.268  -0.212  1.00  0.00           O  
HETATM   43  C26 UNL     1       6.057  -0.381   0.359  1.00  0.00           C  
HETATM   44  O18 UNL     1       6.423  -0.370   1.720  1.00  0.00           O  
HETATM   45  C27 UNL     1       4.825   0.046  -0.061  1.00  0.00           C  
HETATM   46  H1  UNL     1       0.512   1.912  -0.331  1.00  0.00           H  
HETATM   47  H2  UNL     1       1.133   2.219  -1.949  1.00  0.00           H  
HETATM   48  H3  UNL     1       0.614   0.074  -2.805  1.00  0.00           H  
HETATM   49  H4  UNL     1      -3.037   1.245  -1.547  1.00  0.00           H  
HETATM   50  H5  UNL     1      -0.516   4.354   0.728  1.00  0.00           H  
HETATM   51  H6  UNL     1       0.817   5.986   1.925  1.00  0.00           H  
HETATM   52  H7  UNL     1      -2.615   9.255   1.598  1.00  0.00           H  
HETATM   53  H8  UNL     1      -5.104   7.727  -0.077  1.00  0.00           H  
HETATM   54  H9  UNL     1      -4.359   5.507  -0.563  1.00  0.00           H  
HETATM   55  H10 UNL     1      -3.107  -0.130   0.231  1.00  0.00           H  
HETATM   56  H11 UNL     1      -1.512  -0.307   1.724  1.00  0.00           H  
HETATM   57  H12 UNL     1      -1.928  -1.433  -1.703  1.00  0.00           H  
HETATM   58  H13 UNL     1      -3.442  -5.685  -0.759  1.00  0.00           H  
HETATM   59  H14 UNL     1      -4.252  -7.907  -0.319  1.00  0.00           H  
HETATM   60  H15 UNL     1      -3.404  -8.612   2.902  1.00  0.00           H  
HETATM   61  H16 UNL     1      -1.724  -6.250   4.718  1.00  0.00           H  
HETATM   62  H17 UNL     1      -1.430  -3.575   2.289  1.00  0.00           H  
HETATM   63  H18 UNL     1       0.493  -0.635   0.005  1.00  0.00           H  
HETATM   64  H19 UNL     1       1.404  -2.243  -1.088  1.00  0.00           H  
HETATM   65  H20 UNL     1       5.124  -0.441  -3.389  1.00  0.00           H  
HETATM   66  H21 UNL     1       7.288  -1.325  -3.858  1.00  0.00           H  
HETATM   67  H22 UNL     1       8.850  -1.596  -0.900  1.00  0.00           H  
HETATM   68  H23 UNL     1       5.736  -0.032   2.375  1.00  0.00           H  
HETATM   69  H24 UNL     1       4.094   0.407   0.654  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   37
CONECT    3    4
CONECT    4    5   46   47
CONECT    5    6   35   48
CONECT    6    7
CONECT    7    8   20   49
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   19
CONECT   12   13   50
CONECT   13   14   15   15
CONECT   14   51
CONECT   15   16   17
CONECT   16   52
CONECT   17   18   19   19
CONECT   18   53
CONECT   19   54
CONECT   20   21   22   55
CONECT   21   56
CONECT   22   23   35   57
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   27   27   34
CONECT   27   28   58
CONECT   28   29   30   30
CONECT   29   59
CONECT   30   31   32
CONECT   31   60
CONECT   32   33   34   34
CONECT   33   61
CONECT   34   62
CONECT   35   36   63
CONECT   36   64
CONECT   37   38   38   45
CONECT   38   39   65
CONECT   39   40   41   41
CONECT   40   66
CONECT   41   42   43
CONECT   42   67
CONECT   43   44   45   45
CONECT   44   68
CONECT   45   69
END

HMDB0244815
     RDKit          3D
1,3,6-Tri-O-galloyl-beta-D-glucose
 69 72  0  0  0  0  0  0  0  0999 V2000
    2.8626    0.4658   -3.0635 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    0.4916   -1.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2758    0.9364   -0.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    1.3894   -1.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.3787   -1.8487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104    0.9426   -2.0998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    1.1772   -1.0985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7306    2.4364   -0.5216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722    3.4322   -0.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7435    3.1934   -1.1425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650    4.7637    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883    5.1073    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0899    6.3628    1.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049    6.6978    1.8694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0730    7.3215    1.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573    8.5679    1.6827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2539    6.9830    0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355    7.9659    0.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4315    5.7308   -0.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    0.0671   -0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2366    0.3219    1.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4711   -1.1759   -0.7399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5968   -2.2225    0.1810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -3.3834   -0.2128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033   -3.4699   -1.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4204   -4.5242    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0666   -5.6694    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2499   -6.7628    1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9111   -7.9097    0.6340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7656   -6.7153    2.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9248   -7.7901    3.2391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1102   -5.5690    2.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6060   -5.4658    4.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9402   -4.4858    1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -0.8335   -0.9486 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6182   -1.9009   -1.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4833    0.0290   -1.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -0.4227   -2.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6244   -0.8562   -1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5335   -1.3124   -2.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9563   -0.8340   -0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1966   -1.2680   -0.2122 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0567   -0.3808    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4226   -0.3697    1.7196 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8252    0.0461   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5116    1.9121   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331    2.2186   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6139    0.0741   -2.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    1.2446   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157    4.3536    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    5.9855    1.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6148    9.2546    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1041    7.7269   -0.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3591    5.5074   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1067   -0.1300    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123   -0.3065    1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281   -1.4328   -1.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4418   -5.6852   -0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2516   -7.9069   -0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4039   -8.6123    2.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -6.2504    4.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296   -3.5748    2.2895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4930   -0.6351    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4038   -2.2432   -1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1240   -0.4407   -3.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2877   -1.3254   -3.8576 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8495   -1.5962   -0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356   -0.0321    2.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0937    0.4075    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
  7 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  2  0
 22 35  1  0
 35 36  1  0
  2 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  1  0
 43 45  2  0
 35  5  1  0
 45 37  1  0
 19 11  1  0
 34 26  1  0
  4 46  1  0
  4 47  1  0
  5 48  1  0
  7 49  1  0
 12 50  1  0
 14 51  1  0
 16 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 21 56  1  0
 22 57  1  0
 27 58  1  0
 29 59  1  0
 31 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  0
 36 64  1  0
 38 65  1  0
 40 66  1  0
 42 67  1  0
 44 68  1  0
 45 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[3,5-Dihydroxy-4,6-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₇H₂₄O₁₈

Average Molecular Weight

636.471

Monoisotopic Molecular Weight

636.096263933

IUPAC Name

[3,5-dihydroxy-4,6-bis(3,4,5-trihydroxybenzoyloxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Traditional Name

tannic acid

CAS Registry Number

Not Available

SMILES

OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H24O18/c28-11-1-8(2-12(29)18(11)34)24(39)42-7-17-21(37)23(44-25(40)9-3-13(30)19(35)14(31)4-9)22(38)27(43-17)45-26(41)10-5-15(32)20(36)16(33)6-10/h1-6,17,21-23,27-38H,7H2

InChI Key

RNKMOGIPOMVCHO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Not Available

Direct Parent

Tannins

Alternative Parents

Substituents

Tannin
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Oxane
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.94	ALOGPS
logP	1.82	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	310.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	143.22 m³·mol⁻¹	ChemAxon
Polarizability	59.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	239.142	30932474
DeepCCS	[M-H]-	237.317	30932474
DeepCCS	[M-2H]-	270.559	30932474
DeepCCS	[M+Na]+	244.748	30932474
AllCCS	[M+H]+	231.2	32859911
AllCCS	[M+H-H2O]+	230.2	32859911
AllCCS	[M+NH4]+	232.1	32859911
AllCCS	[M+Na]+	232.4	32859911
AllCCS	[M-H]-	226.0	32859911
AllCCS	[M+Na-2H]-	227.6	32859911
AllCCS	[M+HCOO]-	229.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	12.9748 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.46 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1571.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	164.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	112.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	591.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	477.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	923.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	734.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	212.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1582.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	281.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	513.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	294.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	724.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,3,6-Tri-O-galloyl-beta-D-glucose	OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1	8033.9	Standard polar	33892256
1,3,6-Tri-O-galloyl-beta-D-glucose	OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1	5220.5	Standard non polar	33892256
1,3,6-Tri-O-galloyl-beta-D-glucose	OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1	5944.9	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

219294

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

250395

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 1,3,6-Tri-O-galloyl-beta-D-glucose (HMDB0244815)

MOL for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

3D MOL for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

3D SDF for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

3D-SDF for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

PDB for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

3D PDB for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

SMILES for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

INCHI for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

Structure for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

3D Structure for HMDB0244815 (1,3,6-Tri-O-galloyl-beta-D-glucose)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized