NP-MRD: Showing NP-Card for 6'-O-Galloyl paeoniflorin (NP0138194)

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Record Information

Version

2.0

Created at

2022-05-31 17:15:22 UTC

Updated at

2022-05-31 17:15:22 UTC

NP-MRD ID

NP0138194

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6'-O-Galloyl paeoniflorin

Description

Paeoniflorin, galloyl-, also known as galloyl-paeoniflorin, belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 6'-O-Galloyl paeoniflorin is found in Paeonia lactiflora. Based on a literature review very few articles have been published on Paeoniflorin, galloyl-.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312219152D          

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    2.1764    1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652305312219152D          

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   -0.8996    0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2207   -0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0394   -0.8331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605   -1.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8629   -2.2511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1791   -1.6949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002   -2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -2.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6400   -3.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -1.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6352   -2.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4954   -1.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9930   -0.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6767   -1.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3972    0.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2159    0.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0761    1.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5737    2.1048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2574    1.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0637    2.3086    0.0000 O   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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  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  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  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 31 39  1  0  0  0  0
 26 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 24 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC3(O)OC(O1)C1(COC(=O)C4=CC=CC=C4)C3CC21OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O15/c1-27-11-29(39)18-9-30(27,28(18,26(44-27)45-29)12-41-23(37)13-5-3-2-4-6-13)43-25-22(36)21(35)20(34)17(42-25)10-40-24(38)14-7-15(31)19(33)16(32)8-14/h2-8,17-18,20-22,25-26,31-36,39H,9-12H2,1H3

> <INCHI_KEY>
KLFIUQCKSSAFFU-UHFFFAOYSA-N

> <FORMULA>
C30H32O15

> <MOLECULAR_WEIGHT>
632.571

> <EXACT_MASS>
632.17412033

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
60.40927085929665

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[6-({2-[(benzoyloxy)methyl]-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-3-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <JCHEM_LOGP>
1.1980539083333337

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.095096978337565

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.10774166068763

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490929336396656

> <JCHEM_POLAR_SURFACE_AREA>
231.12999999999997

> <JCHEM_REFRACTIVITY>
145.06840000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[6-({2-[(benzoyloxy)methyl]-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-3-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  C   UNK     0       4.063   3.079   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.251   1.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.762   0.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.424  -0.621   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.962  -0.691   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.608  -2.184   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.158  -1.596   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.590   0.054   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.584  -1.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.287  -2.014   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.358  -3.552   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.725  -4.261   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.022  -3.430   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.796  -5.799   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.163  -6.507   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.234  -8.045   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.937  -8.876   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.569  -8.168   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.499  -6.629   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.632  -0.388   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.840  -0.259   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.905   0.624   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.977   1.853   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.448   1.662   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.151   0.244   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.679   0.054   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.279  -1.365   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.807  -1.555   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -4.406  -2.974   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.477  -4.202   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.934  -3.164   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.534  -4.582   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.062  -4.773   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.661  -6.191   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.991  -3.544   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -10.519  -3.734   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -8.391  -2.126   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -9.320  -0.897   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.863  -1.936   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.608   1.282   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -4.136   1.092   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.009   2.701   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.937   3.929   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -0.480   2.891   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       0.119   4.309   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6   20                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    2                                                       
CONECT    9    7   10   20   22                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    9    4   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    2    9   23                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   44                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   40                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   31                                                       
CONECT   40   26   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   24   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

View in JSmol

Synonyms

Value	Source
Galloyl-paeoniflorin	MeSH
Galloylpaeoniflorin	MeSH

Chemical Formula

C₃₀H₃₂O₁₅

Average Mass

632.5710 Da

Monoisotopic Mass

632.17412 Da

IUPAC Name

[6-({2-[(benzoyloxy)methyl]-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-3-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Traditional Name

[6-({2-[(benzoyloxy)methyl]-6-hydroxy-8-methyl-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-3-yl}oxy)-3,4,5-trihydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

122965-41-7

SMILES

CC12CC3(O)OC(O1)C1(COC(=O)C4=CC=CC=C4)C3CC21OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C30H32O15/c1-27-11-29(39)18-9-30(27,28(18,26(44-27)45-29)12-41-23(37)13-5-3-2-4-6-13)43-25-22(36)21(35)20(34)17(42-25)10-40-24(38)14-7-15(31)19(33)16(32)8-14/h2-8,17-18,20-22,25-26,31-36,39H,9-12H2,1H3

InChI Key

KLFIUQCKSSAFFU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Paeonia lactiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
O-glycosyl compound
Glycosyl compound
Monoterpenoid
Nopinane monoterpenoid
Aromatic monoterpenoid
Pinane monoterpenoid
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoic acid or derivatives
Furofuran
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxepane
Phenol
Meta-dioxane
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Tetrahydrofuran
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Hemiacetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.2	ChemAxon
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	231.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	145.07 m³·mol⁻¹	ChemAxon
Polarizability	60.41 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

433028

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

494717

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 6'-O-Galloyl paeoniflorin (NP0138194)

MOL for NP0138194 (6'-O-Galloyl paeoniflorin)

3D MOL for NP0138194 (6'-O-Galloyl paeoniflorin)

3D SDF for NP0138194 (6'-O-Galloyl paeoniflorin)

3D-SDF for NP0138194 (6'-O-Galloyl paeoniflorin)

PDB for NP0138194 (6'-O-Galloyl paeoniflorin)

3D PDB for NP0138194 (6'-O-Galloyl paeoniflorin)

SMILES for NP0138194 (6'-O-Galloyl paeoniflorin)

INCHI for NP0138194 (6'-O-Galloyl paeoniflorin)

Structure for NP0138194 (6'-O-Galloyl paeoniflorin)

3D Structure for NP0138194 (6'-O-Galloyl paeoniflorin)