NP-MRD: Showing NP-Card for 4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate (NP0152244)

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Record Information

Version

2.0

Created at

2022-09-02 08:40:50 UTC

Updated at

2022-09-02 08:40:50 UTC

NP-MRD ID

NP0152244

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate

Description

[3,4-Dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)-6-(3,4,5-trihydroxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group. 4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate is found in Eugenia hyemalis. [3,4-Dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)-6-(3,4,5-trihydroxyphenoxy)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


  Mrv1533004171506372D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171506372D          

 43 46  0  0  0  0            999 V2000
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    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
  9 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 20 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 35 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152244

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC2=CC(O)=C(O)C(O)=C2)OC1COC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H24O17/c27-11-1-8(2-12(28)18(11)33)24(38)40-7-17-21(36)22(37)23(43-25(39)9-3-13(29)19(34)14(30)4-9)26(42-17)41-10-5-15(31)20(35)16(32)6-10/h1-6,17,21-23,26-37H,7H2

> <INCHI_KEY>
HTASWIJLVDONEM-UHFFFAOYSA-N

> <FORMULA>
C26H24O17

> <MOLECULAR_WEIGHT>
608.461

> <EXACT_MASS>
608.101349313

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
55.96418358846492

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.6601242033333325

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.36656332232885

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.789954898626661

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548902248569363

> <JCHEM_POLAR_SURFACE_AREA>
293.59

> <JCHEM_REFRACTIVITY>
137.6554

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9                                                       
CONECT   18    5   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20                                                       
CONECT   29   18   30                                                       
CONECT   30   29    2   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   43                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   35                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Value	Source
[3,4-Dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)-6-(3,4,5-trihydroxyphenoxy)oxan-2-yl]methyl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₆H₂₄O₁₇

Average Mass

608.4610 Da

Monoisotopic Mass

608.10135 Da

IUPAC Name

4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1C(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC2=CC(O)=C(O)C(O)=C2)OC1COC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C26H24O17/c27-11-1-8(2-12(28)18(11)33)24(38)40-7-17-21(36)22(37)23(43-25(39)9-3-13(29)19(34)14(30)4-9)26(42-17)41-10-5-15(31)20(35)16(32)6-10/h1-6,17,21-23,26-37H,7H2

InChI Key

HTASWIJLVDONEM-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
Eugenia hyemalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=fatty aliphatic tail or organyl group and R'=methyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid methyl esters

Alternative Parents

Substituents

Fatty acid methyl ester
Methyl ester
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.02	ALOGPS
logP	1.66	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.79	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	293.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	137.66 m³·mol⁻¹	ChemAxon
Polarizability	55.96 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

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 4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate (NP0152244)

MOL for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0152244 (4,5-dihydroxy-6-[(3,4,5-trihydroxybenzoyloxy)methyl]-2-(3,4,5-trihydroxyphenoxy)oxan-3-yl 3,4,5-trihydroxybenzoate)