NP-MRD: Showing NP-Card for (3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione (NP0315781)

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Record Information

Version

2.0

Created at

2022-09-11 14:35:22 UTC

Updated at

2022-09-11 14:35:22 UTC

NP-MRD ID

NP0315781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione

Description

Trigalloylglucose belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. (3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione is found in Arctostaphylos uva-ursi, Fragaria ananassa and Punica granatum. Based on a literature review very few articles have been published on trigalloylglucose.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112216352D          

 45 47  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112216352D          

 45 47  0  0  1  0            999 V2000
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    3.7754   -3.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -4.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1086   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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
  9 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  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  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 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>
NP0315781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H](O)[C@@H](O)[C@@](O)(C(=O)C1=CC(O)=C(O)C(O)=C1)[C@@](O)(C(=O)C(=O)C1=CC(O)=C(O)C(O)=C1)C(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O18/c28-7-17(35)24(42)26(44,22(40)9-3-13(31)20(38)14(32)4-9)27(45,23(41)10-5-15(33)21(39)16(34)6-10)25(43)18(36)8-1-11(29)19(37)12(30)2-8/h1-6,17,24,28-35,37-39,42,44-45H,7H2/t17-,24-,26+,27+/m1/s1

> <INCHI_KEY>
UHDJFCOJSFPKML-UOAHBSSISA-N

> <FORMULA>
C27H24O18

> <MOLECULAR_WEIGHT>
636.471

> <EXACT_MASS>
636.096263933

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.313105520638544

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1R,2R)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione

> <JCHEM_LOGP>
-1.0254452586666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.238733883907327

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.755525952865119

> <JCHEM_PKA_STRONGEST_BASIC>
-6.037086796257083

> <JCHEM_POLAR_SURFACE_AREA>
351.5

> <JCHEM_REFRACTIVITY>
145.2203

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1R,2R)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       1.127  -7.287   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.357  -5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.127  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.280  -3.994   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.207  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.207  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.747  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.517  -5.954   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.517  -3.286   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.747  -1.953   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.517  -0.619   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.747   0.715   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.057  -0.619   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.827   0.715   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.827  -1.953   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.367  -1.953   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.057  -3.286   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.207  -6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.874  -6.930   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.541  -6.930   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.047  -6.610   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.541  -8.470   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.875  -9.240   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.183  -5.954   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.953  -7.287   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.493  -7.287   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.263  -8.621   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -4.263  -5.954   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -5.803  -5.954   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -3.493  -4.620   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -4.263  -3.286   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -1.953  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   18                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9                                                       
CONECT   18    5   19   20   31                                             
CONECT   19   18                                                            
CONECT   20   18   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   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37    2   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   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₄O₁₈

Average Mass

636.4710 Da

Monoisotopic Mass

636.09626 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@@H](O)[C@@H](O)[C@@](O)(C(=O)C1=CC(O)=C(O)C(O)=C1)[C@@](O)(C(=O)C(=O)C1=CC(O)=C(O)C(O)=C1)C(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C27H24O18/c28-7-17(35)24(42)26(44,22(40)9-3-13(31)20(38)14(32)4-9)27(45,23(41)10-5-15(33)21(39)16(34)6-10)25(43)18(36)8-1-11(29)19(37)12(30)2-8/h1-6,17,24,28-35,37-39,42,44-45H,7H2/t17-,24-,26+,27+/m1/s1

InChI Key

UHDJFCOJSFPKML-UOAHBSSISA-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
Arctostaphylos uva-ursi	LOTUS Database	35616633
Fragaria x ananassa	LOTUS Database	35616633
Punica granatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Dibenzylbutane lignans

Sub Class

Not Available

Direct Parent

Dibenzylbutane lignans

Alternative Parents

Substituents

Dibenzylbutane lignan skeleton
Alkyl-phenylketone
Butyrophenone
Benzenetriol
Phenylketone
Fatty alcohol
Pyrogallol derivative
Benzoyl
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Benzenoid
Alpha-diketone
Monosaccharide
Monocyclic benzene moiety
Acyloin
Beta-hydroxy ketone
Tertiary alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Polyol
Primary alcohol
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00035191

Chemspider ID

66424893

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90116889

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione (NP0315781)

MOL for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

3D MOL for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

3D SDF for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

3D-SDF for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

PDB for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

3D PDB for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

SMILES for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

INCHI for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

Structure for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)

3D Structure for NP0315781 ((3s,4s)-3,4-dihydroxy-3-(3,4,5-trihydroxybenzoyl)-1,5-bis(3,4,5-trihydroxyphenyl)-4-[(1r,2r)-1,2,3-trihydroxypropyl]pentane-1,2,5-trione)