NP-MRD: Showing NP-Card for (2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol (NP0240301)

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Record Information

Version

2.0

Created at

2022-09-07 00:05:27 UTC

Updated at

2022-09-07 00:05:28 UTC

NP-MRD ID

NP0240301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol

Description

(2S,3R,4R,5R,6R)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol is found in Sanguisorba minor. Based on a literature review very few articles have been published on (2S,3R,4R,5R,6R)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202052D          

 43 46  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072202052D          

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   -3.4222   -2.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -2.8377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8091   -2.6945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9966   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7111   -1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1842   -2.6945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4289   -2.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990   -1.8775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3511   -1.3696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  3 11  1  0  0  0  0
 12  2  1  1  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 16 19  1  1  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  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  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
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 30 35  1  0  0  0  0
 26 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  6  0  0  0
 38 39  1  0  0  0  0
 36 40  1  0  0  0  0
 12 40  1  0  0  0  0
 40 41  1  6  0  0  0
 40 42  1  1  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@]1(OC2=CC=CC=C2)O[C@](OO)(C(=O)C2=CC(O)=C(O)C(O)=C2)[C@](O)(OO)[C@@](O)(OO)[C@]1(O)OOC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O18/c26-13-21(37-15-7-3-1-4-8-15)23(31,43-38-16-9-5-2-6-10-16)25(33,42-36)24(32,41-35)22(39-21,40-34)20(30)14-11-17(27)19(29)18(28)12-14/h1-12,26-29,31-36H,13H2/t21-,22+,23-,24+,25+/m1/s1

> <INCHI_KEY>
LHRWCCNJXPOMNL-KJWQXZETSA-N

> <FORMULA>
C25H24O18

> <MOLECULAR_WEIGHT>
612.449

> <EXACT_MASS>
612.096263933

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.60679857401076

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6R)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
3.336348712666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
7.267551553491818

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.694461574236085

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3153237221391985

> <JCHEM_POLAR_SURFACE_AREA>
283.97999999999996

> <JCHEM_REFRACTIVITY>
131.81540000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6R)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       3.313  -6.209   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.980  -6.979   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.980  -8.519   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.313  -9.289   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.313 -10.829   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.647 -11.599   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.980 -11.599   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.980 -13.139   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.646 -10.829   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.688 -11.599   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.646  -9.289   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.646  -6.209   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.636  -5.030   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.153  -5.297   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.119  -7.657   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.397  -7.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.870  -9.371   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.199 -10.479   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.731  -8.694   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.731 -10.234   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.397 -11.004   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.397 -12.544   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.731 -13.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.065 -12.544   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.065 -11.004   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.387  -6.744   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.377  -7.924   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.721  -5.974   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.054  -6.744   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.388  -5.974   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.722  -6.744   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.055  -5.974   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.055  -4.434   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -7.722  -3.664   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.388  -4.434   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.860  -5.297   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.377  -5.030   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -1.860  -3.757   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -3.194  -2.987   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.344  -5.030   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.801  -3.999   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -0.558  -3.505   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       0.655  -2.557   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3                                                       
CONECT   12    2   13   15   40                                             
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   19   26                                             
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   16   27   28   36                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   30                                                       
CONECT   36   26   37   38   40                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   36   12   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₁₈

Average Mass

612.4490 Da

Monoisotopic Mass

612.09626 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@@]1(OC2=CC=CC=C2)O[C@](OO)(C(=O)C2=CC(O)=C(O)C(O)=C2)[C@](O)(OO)[C@@](O)(OO)[C@]1(O)OOC1=CC=CC=C1

InChI Identifier

InChI=1S/C25H24O18/c26-13-21(37-15-7-3-1-4-8-15)23(31,43-38-16-9-5-2-6-10-16)25(33,42-36)24(32,41-35)22(39-21,40-34)20(30)14-11-17(27)19(29)18(28)12-14/h1-12,26-29,31-36H,13H2/t21-,22+,23-,24+,25+/m1/s1

InChI Key

LHRWCCNJXPOMNL-KJWQXZETSA-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
Sanguisorba minor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Pyrogallol derivative
Benzenetriol
Phenoxy compound
Aryl alkyl ketone
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Benzenoid
Pyran
Oxane
Monosaccharide
Monocyclic benzene moiety
Hydroperoxide
Alkyl hydroperoxide
Oxacycle
Organoheterocyclic compound
Polyol
Peroxol
Acetal
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
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

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

162817108

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol (NP0240301)

MOL for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

3D MOL for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

3D SDF for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

3D-SDF for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

PDB for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

3D PDB for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

SMILES for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

INCHI for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

Structure for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)

3D Structure for NP0240301 ((2s,3r,4r,5r,6r)-2,3,4-trihydroperoxy-6-(hydroxymethyl)-6-phenoxy-5-(phenylperoxy)-2-(3,4,5-trihydroxybenzoyl)oxane-3,4,5-triol)