NP-MRD: Showing NP-Card for Gallotannin (NP0137394)

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Record Information

Version

2.0

Created at

2022-05-30 16:51:12 UTC

Updated at

2022-05-30 16:51:13 UTC

NP-MRD ID

NP0137394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gallotannin

Description

Tannin 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) that 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. Tannin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, tannin is found, on average, in the highest concentration in a few different foods, such as nances, tea, and black walnuts and in a lower concentration in potato, common thymes, and papaya. Tannin has also been detected, but not quantified in, several different foods, such as coconuts, dandelions, roman camomiles, german camomiles, and figs. This could make tannin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220292D          

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M  END

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  Mrv0541 02231220292D          

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   17.3823  -10.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8092  -10.8836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8092  -12.5340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3823  -13.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  6 13  1  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  0  0  0  0
 12 16  1  0  0  0  0
 11 17  1  0  0  0  0
 10 18  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  8 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 26 20  1  6  0  0  0
 30 24  1  1  0  0  0
 25 31  1  6  0  0  0
 29 32  1  6  0  0  0
 28 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
 40 42  1  0  0  0  0
 39 43  1  0  0  0  0
 38 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)O[C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]1[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C26H20O18/c27-8-1-5(2-9(28)14(8)31)22(38)42-25-19(36)21-20(37)26(44-25)43-24(40)7-4-11(30)16(33)18(35)13(7)12-6(23(39)41-21)3-10(29)15(32)17(12)34/h1-4,19-21,25-37H/t19-,20-,21-,25+,26-/m0/s1

> <INCHI_KEY>
VXMKYRQZQXVKGB-CWWHNZPOSA-N

> <FORMULA>
C26H20O18

> <MOLECULAR_WEIGHT>
620.4262

> <EXACT_MASS>
620.064963836

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
52.55005627305799

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,18R,20S,21S,22S)-6,7,8,11,12,13,21,22-octahydroxy-3,16-dioxo-2,17,19-trioxatetracyclo[16.3.1.0⁴,⁹.0¹⁰,¹⁵]docosa-4(9),5,7,10,12,14-hexaen-20-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.3613629793333335

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.915566997602659

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3996401939191125

> <JCHEM_PKA_STRONGEST_BASIC>
-5.549137792101363

> <JCHEM_POLAR_SURFACE_AREA>
310.65999999999997

> <JCHEM_REFRACTIVITY>
137.36309999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,18R,20S,21S,22S)-6,7,8,11,12,13,21,22-octahydroxy-3,16-dioxo-2,17,19-trioxatetracyclo[16.3.1.0⁴,⁹.0¹⁰,¹⁵]docosa-4(9),5,7,10,12,14-hexaen-20-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      18.070 -17.653   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.145 -19.187   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.514 -19.894   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.808 -19.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.733 -17.524   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.364 -16.818   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.503 -16.192   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.873 -15.486   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.948 -13.946   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.653 -13.111   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.284 -13.817   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.209 -15.358   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      17.770 -15.673   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      16.701 -16.946   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      16.845 -20.022   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      18.321 -14.454   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      18.984 -12.988   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      21.723 -11.576   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      21.701 -20.316   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      23.129 -20.888   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      20.749 -21.530   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      24.408 -15.631   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      24.980 -14.203   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      25.617 -16.583   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      25.745 -19.524   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.659 -20.610   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      25.788 -20.781   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      26.708 -20.086   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.847 -18.936   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.125 -18.038   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      23.750 -18.391   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      28.329 -18.514   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      28.441 -21.086   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      29.778 -20.316   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      31.110 -21.086   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      29.778 -19.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      31.110 -22.627   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      32.447 -23.397   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      33.779 -22.627   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      33.779 -21.086   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      32.447 -20.316   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      35.111 -20.316   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      35.111 -23.397   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      32.447 -24.937   0.000  0.00  0.00           O+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1   13                                                  
CONECT    7    5    8   12                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11    7   16                                                  
CONECT   13    6                                                            
CONECT   14    1                                                            
CONECT   15    2                                                            
CONECT   16   12                                                            
CONECT   17   11                                                            
CONECT   18   10                                                            
CONECT   19    4   20   21                                                  
CONECT   20   19   26                                                       
CONECT   21   19                                                            
CONECT   22    8   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   30                                                       
CONECT   25   26   30   31                                                  
CONECT   26   25   27   20                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   25   24                                                  
CONECT   31   25                                                            
CONECT   32   29                                                            
CONECT   33   28   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34   37   41                                                  
CONECT   36   34                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   44                                                  
CONECT   39   38   40   43                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40   35                                                       
CONECT   42   40                                                            
CONECT   43   39                                                            
CONECT   44   38                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
Corilagin	HMDB
Gallotannic acid	HMDB
Gallotannin	HMDB
Quebracho	HMDB
Tannin (tannic acid)	HMDB
(1S,18R,20S,21S,22S)-6,7,8,11,12,13,21,22-Octahydroxy-3,16-dioxo-2,17,19-trioxatetracyclo[16.3.1.0⁴,⁹.0¹⁰,¹⁵]docosa-4,6,8,10,12,14-hexaen-20-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₆H₂₀O₁₈

Average Mass

620.4262 Da

Monoisotopic Mass

620.06496 Da

IUPAC Name

(1S,18R,20S,21S,22S)-6,7,8,11,12,13,21,22-octahydroxy-3,16-dioxo-2,17,19-trioxatetracyclo[16.3.1.0⁴,⁹.0¹⁰,¹⁵]docosa-4(9),5,7,10,12,14-hexaen-20-yl 3,4,5-trihydroxybenzoate

Traditional Name

(1S,18R,20S,21S,22S)-6,7,8,11,12,13,21,22-octahydroxy-3,16-dioxo-2,17,19-trioxatetracyclo[16.3.1.0⁴,⁹.0¹⁰,¹⁵]docosa-4(9),5,7,10,12,14-hexaen-20-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)O[C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(C=C(O)C(O)=C3O)C(=O)O[C@@H]1[C@@H]2O

InChI Identifier

InChI=1S/C26H20O18/c27-8-1-5(2-9(28)14(8)31)22(38)42-25-19(36)21-20(37)26(44-25)43-24(40)7-4-11(30)16(33)18(35)13(7)12-6(23(39)41-21)3-10(29)15(32)17(12)34/h1-4,19-21,25-37H/t19-,20-,21-,25+,26-/m0/s1

InChI Key

VXMKYRQZQXVKGB-CWWHNZPOSA-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

Not Available

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) that 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
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
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Lactone
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.89	ALOGPS
logP	1.36	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.4	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	3	ChemAxon
Refractivity	137.36 m³·mol⁻¹	ChemAxon
Polarizability	52.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0005790

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001111

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tannin

METLIN ID

Not Available

PubChem Compound

22833652

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gallotannin (NP0137394)

MOL for NP0137394 (Gallotannin)

3D MOL for NP0137394 (Gallotannin)

3D SDF for NP0137394 (Gallotannin)

3D-SDF for NP0137394 (Gallotannin)

PDB for NP0137394 (Gallotannin)

3D PDB for NP0137394 (Gallotannin)

SMILES for NP0137394 (Gallotannin)

INCHI for NP0137394 (Gallotannin)

Structure for NP0137394 (Gallotannin)

3D Structure for NP0137394 (Gallotannin)