NP-MRD: Showing NP-Card for (-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose (NP0072632)

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Record Information

Version

2.0

Created at

2022-04-28 17:57:08 UTC

Updated at

2022-04-28 17:57:08 UTC

NP-MRD ID

NP0072632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose

Description

6-O-beta-D-Glucopyranosyl-beta-D-glucopyranose 1-(3,4-dihydroxy-trans-cinnamate) belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. (-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose is found in Balanophora japonica and Brassica napus. Based on a literature review very few articles have been published on 6-O-beta-D-Glucopyranosyl-beta-D-glucopyranose 1-(3,4-dihydroxy-trans-cinnamate).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219572D          

 35 37  0  0  1  0            999 V2000
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   -4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -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
   -3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    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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   -3.9025    0.9833   -0.6033 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282219572D          

 35 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0072632

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O14/c22-6-11-14(26)16(28)18(30)20(33-11)32-7-12-15(27)17(29)19(31)21(34-12)35-13(25)4-2-8-1-3-9(23)10(24)5-8/h1-5,11-12,14-24,26-31H,6-7H2/b4-2+/t11-,12-,14-,15-,16+,17+,18-,19-,20-,21+/m1/s1

> <INCHI_KEY>
QJGHVFYJIDLXEM-CQGBVQOQSA-N

> <FORMULA>
C21H28O14

> <MOLECULAR_WEIGHT>
504.441

> <EXACT_MASS>
504.147905582

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.664749697073034

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-1.37

> <JCHEM_LOGP>
-2.276614789

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.826980148567264

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.207563716108178

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483773177512537

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999995

> <JCHEM_REFRACTIVITY>
111.86619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335 -12.320   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      -6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.004   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -13.337   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -14.670   3.850   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -16.004   4.620   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -17.338   2.310   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0     -17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -14.670  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8                                                            
CONECT   12    7                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22   17                                                            
CONECT   23   16   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   35                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28                                                            
CONECT   34   27                                                            
CONECT   35   26                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
6-O-b-D-Glucopyranosyl-b-D-glucopyranose 1-(3,4-dihydroxy-trans-cinnamate)	Generator
6-O-b-D-Glucopyranosyl-b-D-glucopyranose 1-(3,4-dihydroxy-trans-cinnamic acid)	Generator
6-O-beta-D-Glucopyranosyl-beta-D-glucopyranose 1-(3,4-dihydroxy-trans-cinnamic acid)	Generator
6-O-Β-D-glucopyranosyl-β-D-glucopyranose 1-(3,4-dihydroxy-trans-cinnamate)	Generator
6-O-Β-D-glucopyranosyl-β-D-glucopyranose 1-(3,4-dihydroxy-trans-cinnamic acid)	Generator

Chemical Formula

C₂₁H₂₈O₁₄

Average Mass

504.4410 Da

Monoisotopic Mass

504.14791 Da

IUPAC Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H28O14/c22-6-11-14(26)16(28)18(30)20(33-11)32-7-12-15(27)17(29)19(31)21(34-12)35-13(25)4-2-8-1-3-9(23)10(24)5-8/h1-5,11-12,14-24,26-31H,6-7H2/b4-2+/t11-,12-,14-,15-,16+,17+,18-,19-,20-,21+/m1/s1

InChI Key

QJGHVFYJIDLXEM-CQGBVQOQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Balanophora japonica	Plant	KNApSAcK
Brassica napus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acid glycosides

Alternative Parents

Substituents

Hydroxycinnamic acid glycoside
O-cinnamoyl glycoside
Coumaric acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Fatty acyl
Monocyclic benzene moiety
Oxane
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Carbonyl group
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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
logP	-1.4	ALOGPS
logP	-2.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	236.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	111.87 m³·mol⁻¹	ChemAxon
Polarizability	47.66 Å³	ChemAxon
Number of Rings	3	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

9246334

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11071182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose (NP0072632)

MOL for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

3D MOL for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

3D SDF for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

3D-SDF for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

PDB for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

3D PDB for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

SMILES for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

INCHI for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

Structure for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)

3D Structure for NP0072632 ((-)-1-O-(E)-Caffeoyl-4,6-di-O-galloyl-beta-D-glucopyranose)