NP-MRD: Showing NP-Card for 4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate (NP0175348)

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Record Information

Version

2.0

Created at

2022-09-03 12:47:03 UTC

Updated at

2022-09-03 12:47:03 UTC

NP-MRD ID

NP0175348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate

Description

4'-O-Galloylsucrose belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. 4'-O-Galloylsucrose is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4'-O-Galloylsucrose has been detected, but not quantified in, green vegetables. 4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate is found in Rheum palmatum. This could make 4'-O-galloylsucrose a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310582D          

 34 36  0  0  0  0            999 V2000
   -2.0841    0.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2402    1.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549    6.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6806    1.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3352    4.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4197    1.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691   -0.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7251    0.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5480    6.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1956    2.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3895   -0.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041    6.8112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0660    5.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6294    2.5747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    3.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348    1.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5140    5.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169    3.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6099    7.1542    0.0000 O   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


  Mrv0541 05061310582D          

 34 36  0  0  0  0            999 V2000
   -2.0841    0.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2402    1.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3549    6.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0175348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O15/c20-3-9-12(26)13(27)14(28)18(31-9)34-19(5-22)16(29)15(10(4-21)33-19)32-17(30)6-1-7(23)11(25)8(24)2-6/h1-2,9-10,12-16,18,20-29H,3-5H2

> <INCHI_KEY>
VQNOKSMTUKSLMO-UHFFFAOYSA-N

> <FORMULA>
C19H26O15

> <MOLECULAR_WEIGHT>
494.4007

> <EXACT_MASS>
494.127170162

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
44.78114976092608

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
-1.47

> <JCHEM_LOGP>
-2.94423108

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.183626187623345

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.103036868379565

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4558459877293464

> <JCHEM_POLAR_SURFACE_AREA>
256.28999999999996

> <JCHEM_REFRACTIVITY>
104.5388

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.80e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -3.890   1.068   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.048   2.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.529  11.890   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.270   3.560   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.626   8.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.517   2.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.796  -0.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.954   1.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.023  11.570   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.365   4.806   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.327  -0.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.008  12.714   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.514  12.394   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.990  10.929   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.175   4.806   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.651   6.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.612   3.721   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.959   9.785   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.405   7.176   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.005  13.355   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.802   3.721   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.132   8.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.169  -1.584   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.485   1.551   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -7.232  -1.262   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.468  14.179   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.544  13.539   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.496  10.609   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -3.115   6.747   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -4.238   5.128   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.547  10.105   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.080   3.560   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.841   6.271   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.435   8.320   0.000  0.00  0.00           O+0
CONECT    1    6    7                                                       
CONECT    2    6    8                                                       
CONECT    3    9   20                                                       
CONECT    4   10   21                                                       
CONECT    5   19   22                                                       
CONECT    6    1    2   17                                                  
CONECT    7    1   11   23                                                  
CONECT    8    2   11   24                                                  
CONECT    9    3   12   31                                                  
CONECT   10    4   15   33                                                  
CONECT   11    7    8   25                                                  
CONECT   12    9   13   26                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   18   28                                                  
CONECT   15   10   16   32                                                  
CONECT   16   15   19   29                                                  
CONECT   17    6   30   32                                                  
CONECT   18   14   31   34                                                  
CONECT   19    5   16   33   34                                             
CONECT   20    3                                                            
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
CONECT   25   11                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   16                                                            
CONECT   30   17                                                            
CONECT   31    9   18                                                       
CONECT   32   15   17                                                       
CONECT   33   10   19                                                       
CONECT   34   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₁₉H₂₆O₁₅

Average Mass

494.4007 Da

Monoisotopic Mass

494.12717 Da

IUPAC Name

4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C19H26O15/c20-3-9-12(26)13(27)14(28)18(31-9)34-19(5-22)16(29)15(10(4-21)33-19)32-17(30)6-1-7(23)11(25)8(24)2-6/h1-2,9-10,12-16,18,20-29H,3-5H2

InChI Key

VQNOKSMTUKSLMO-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
Rheum palmatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
O-glycosyl compound
Glycosyl compound
Disaccharide
C-glycosyl compound
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoyl
Ketal
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Primary alcohol
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	-1.5	ALOGPS
logP	-2.9	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	8.1	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	256.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	104.54 m³·mol⁻¹	ChemAxon
Polarizability	44.78 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

HMDB0039284

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018829

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

14055553

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate (NP0175348)

MOL for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0175348 (4-hydroxy-2,5-bis(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxolan-3-yl 3,4,5-trihydroxybenzoate)