NP-MRD: Showing NP-Card for (3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate (NP0185690)

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Record Information

Version

2.0

Created at

2022-09-04 01:12:06 UTC

Updated at

2022-09-04 01:12:06 UTC

NP-MRD ID

NP0185690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate

Description

(3,4,5-Trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as stilbene glycosides. (3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate is found in Fagopyrum megacarpum. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton (3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161507452D          

 39 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161507452D          

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 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  4  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 28 34  1  0  0  0  0
 25 35  2  0  0  0  0
 20 35  1  0  0  0  0
 18 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC2=CC(O)=CC(C=CC3=CC=C(O)C=C3)=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O12/c28-16-5-3-13(4-6-16)1-2-14-7-17(29)11-18(8-14)38-27-25(35)24(34)23(33)21(39-27)12-37-26(36)15-9-19(30)22(32)20(31)10-15/h1-11,21,23-25,27-35H,12H2

> <INCHI_KEY>
YGKDMUYXJBMRBO-UHFFFAOYSA-N

> <FORMULA>
C27H26O12

> <MOLECULAR_WEIGHT>
542.493

> <EXACT_MASS>
542.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
53.37953618150184

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.718926676666666

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.130666651634613

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.065966346473637

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649110481414241

> <JCHEM_POLAR_SURFACE_AREA>
206.6

> <JCHEM_REFRACTIVITY>
135.36460000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336 -19.250   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336 -20.790   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669 -21.560   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669 -23.100   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336 -23.870   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.336 -25.410   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.002 -23.100   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002 -21.560   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
CONECT   17    3   18                                                       
CONECT   18   17   19   36                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   35                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28                                                       
CONECT   35   25   20                                                       
CONECT   36   18   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    2   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(3,4,5-Trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₇H₂₆O₁₂

Average Mass

542.4930 Da

Monoisotopic Mass

542.14243 Da

IUPAC Name

(3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate

Traditional Name

(3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1C(COC(=O)C2=CC(O)=C(O)C(O)=C2)OC(OC2=CC(O)=CC(C=CC3=CC=C(O)C=C3)=C2)C(O)C1O

InChI Identifier

InChI=1S/C27H26O12/c28-16-5-3-13(4-6-16)1-2-14-7-17(29)11-18(8-14)38-27-25(35)24(34)23(33)21(39-27)12-37-26(36)15-9-19(30)22(32)20(31)10-15/h1-11,21,23-25,27-35H,12H2

InChI Key

YGKDMUYXJBMRBO-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
Fagopyrum megacarpum	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
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Glycosyl compound
O-glycosyl compound
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Phenol ether
Phenoxy compound
Styrene
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	2.19	ALOGPS
logP	2.72	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	135.36 m³·mol⁻¹	ChemAxon
Polarizability	53.38 Å³	ChemAxon
Number of Rings	4	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72803885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate (NP0185690)

MOL for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

PDB for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

SMILES for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

INCHI for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

Structure for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0185690 ((3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenoxy}oxan-2-yl)methyl 3,4,5-trihydroxybenzoate)