NP-MRD: Showing NP-Card for (6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate (NP0196629)

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Record Information

Version

2.0

Created at

2022-09-04 14:45:10 UTC

Updated at

2022-09-04 14:45:10 UTC

NP-MRD ID

NP0196629

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

Description

(6-{[1,3-Dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as galloyl esters. (6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate is found in Quercus mongolica. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid (6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-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


  Mrv1533004251505412D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251505412D          

 37 39  0  0  0  0            999 V2000
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 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196629

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(O)C(CO)OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O14/c1-34-14-6-9(2-3-11(14)25)17(28)15(7-24)36-23-21(32)20(31)19(30)16(37-23)8-35-22(33)10-4-12(26)18(29)13(27)5-10/h2-6,15-17,19-21,23-32H,7-8H2,1H3

> <INCHI_KEY>
DXNXRMGZXFPQSX-UHFFFAOYSA-N

> <FORMULA>
C23H28O14

> <MOLECULAR_WEIGHT>
528.463

> <EXACT_MASS>
528.147905582

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.17167850801924

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
-0.42

> <JCHEM_LOGP>
-0.7022421846666673

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.895621463525034

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.101050892971989

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5150192504273194

> <JCHEM_POLAR_SURFACE_AREA>
236.05999999999995

> <JCHEM_REFRACTIVITY>
121.421

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      13.337 -16.940   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.670 -19.250   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.670 -20.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.004 -21.560   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.004 -23.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.338 -23.870   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.672 -23.100   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      17.338 -25.410   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672 -26.180   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.672 -27.720   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.005 -28.490   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      17.338 -28.490   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.338 -30.030   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.004 -27.720   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.670 -28.490   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.004 -26.180   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.337 -23.100   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.003 -20.790   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.669 -21.560   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   36                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   23                                                       
CONECT   32   18   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   16   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
(6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₃H₂₈O₁₄

Average Mass

528.4630 Da

Monoisotopic Mass

528.14791 Da

IUPAC Name

(6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

Traditional Name

(6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(O)C(CO)OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C23H28O14/c1-34-14-6-9(2-3-11(14)25)17(28)15(7-24)36-23-21(32)20(31)19(30)16(37-23)8-35-22(33)10-4-12(26)18(29)13(27)5-10/h2-6,15-17,19-21,23-32H,7-8H2,1H3

InChI Key

DXNXRMGZXFPQSX-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
Quercus mongolica	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
O-glycosyl compound
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Glycosyl compound
Methoxyphenol
Benzoate ester
Pyrogallol derivative
Benzenetriol
Phenol ether
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	-0.42	ALOGPS
logP	-0.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.1	ChemAxon
pKa (Strongest Basic)	-3.5	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	10	ChemAxon
Refractivity	121.42 m³·mol⁻¹	ChemAxon
Polarizability	50.17 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate (NP0196629)

MOL for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D MOL for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D SDF for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

PDB for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D PDB for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

SMILES for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

INCHI for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

Structure for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)

3D Structure for NP0196629 ((6-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3,4,5-trihydroxybenzoate)