NP-MRD: Showing NP-Card for Rhaponticin 2''-O-gallate (NP0138728)

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Record Information

Version

2.0

Created at

2022-06-29 18:33:28 UTC

Updated at

2022-06-29 18:33:28 UTC

NP-MRD ID

NP0138728

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rhaponticin 2''-O-gallate

Description

Rhaponticin 2''-O-gallate belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. Rhaponticin 2''-O-gallate is found in Rheum rhabarbarum, Rheum rhaponticum and Rheum undulatum. It was first documented in 2000 (PMID: 10714491). Based on a literature review very few articles have been published on Rhaponticin 2''-O-gallate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292220332D          

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M  END

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  Mrv1652306292220332D          

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  1  2  1  0  0  0  0
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  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 21 26  1  6  0  0  0
 20 27  1  1  0  0  0
 19 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 35 37  1  0  0  0  0
 34 38  1  0  0  0  0
 33 39  1  0  0  0  0
 13 40  1  0  0  0  0
  4 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(\C=C\C2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O13/c1-38-21-5-4-13(8-18(21)31)2-3-14-6-16(30)11-17(7-14)39-28-26(25(36)24(35)22(12-29)40-28)41-27(37)15-9-19(32)23(34)20(33)10-15/h2-11,22,24-26,28-36H,12H2,1H3/b3-2+/t22-,24-,25+,26-,28-/m1/s1

> <INCHI_KEY>
DBHYLGJAFYCFGS-XJVIDBJFSA-N

> <FORMULA>
C28H28O13

> <MOLECULAR_WEIGHT>
572.519

> <EXACT_MASS>
572.152990962

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.62719629146477

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.5612554110000003

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.786844263831993

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.00603914662027

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810929914690316

> <JCHEM_POLAR_SURFACE_AREA>
215.82999999999996

> <JCHEM_REFRACTIVITY>
141.8278

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -8.002 -21.560   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.003 -20.790   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -9.336 -19.250   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0     -10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0     -13.337 -18.480   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -13.337 -21.560   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0     -10.669 -23.100   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.002 -23.100   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -8.002 -26.180   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.002 -27.720   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -9.336 -28.490   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -10.669 -27.720   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.669 -26.180   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -12.003 -28.490   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -9.336 -30.030   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -6.668 -28.490   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -2.667 -21.560   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   41                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   40                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   21                                                            
CONECT   27   20                                                            
CONECT   28   19   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33   35   38                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   31                                                       
CONECT   37   35                                                            
CONECT   38   34                                                            
CONECT   39   33                                                            
CONECT   40   13                                                            
CONECT   41    4                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Value	Source
Rhaponticin 2''-O-gallic acid	Generator

Chemical Formula

C₂₈H₂₈O₁₃

Average Mass

572.5190 Da

Monoisotopic Mass

572.15299 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

94356-24-8

SMILES

COC1=C(O)C=C(\C=C\C2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)C3=CC(O)=C(O)C(O)=C3)=C2)C=C1

InChI Identifier

InChI=1S/C28H28O13/c1-38-21-5-4-13(8-18(21)31)2-3-14-6-16(30)11-17(7-14)39-28-26(25(36)24(35)22(12-29)40-28)41-27(37)15-9-19(32)23(34)20(33)10-15/h2-11,22,24-26,28-36H,12H2,1H3/b3-2+/t22-,24-,25+,26-,28-/m1/s1

InChI Key

DBHYLGJAFYCFGS-XJVIDBJFSA-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
Rheum rhabarbarum	LOTUS Database	35616633
Rheum rhaponticum	LOTUS Database	35616633
Rheum undulatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Phenolic glycoside
Galloyl ester
Gallic acid or derivatives
Hexose monosaccharide
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Glycosyl compound
O-glycosyl compound
Benzoate ester
Methoxyphenol
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Anisole
Phenoxy compound
Benzoyl
Methoxybenzene
Phenol ether
Styrene
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Oxane
Benzenoid
Monosaccharide
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Ether
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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

Not Available

Chemspider ID

8501205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10325743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matsuda H, Kageura T, Morikawa T, Toguchida I, Harima S, Yoshikawa M: Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages. Bioorg Med Chem Lett. 2000 Feb 21;10(4):323-7. doi: 10.1016/s0960-894x(99)00702-7. [PubMed:10714491 ]

Showing NP-Card for Rhaponticin 2''-O-gallate (NP0138728)

MOL for NP0138728 (Rhaponticin 2''-O-gallate)

3D MOL for NP0138728 (Rhaponticin 2''-O-gallate)

3D SDF for NP0138728 (Rhaponticin 2''-O-gallate)

3D-SDF for NP0138728 (Rhaponticin 2''-O-gallate)

PDB for NP0138728 (Rhaponticin 2''-O-gallate)

3D PDB for NP0138728 (Rhaponticin 2''-O-gallate)

SMILES for NP0138728 (Rhaponticin 2''-O-gallate)

INCHI for NP0138728 (Rhaponticin 2''-O-gallate)

Structure for NP0138728 (Rhaponticin 2''-O-gallate)

3D Structure for NP0138728 (Rhaponticin 2''-O-gallate)