NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate (NP0266569)

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Record Information

Version

2.0

Created at

2022-09-08 10:57:12 UTC

Updated at

2022-09-08 10:57:12 UTC

NP-MRD ID

NP0266569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate

Description

CHEMBL463281 belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on CHEMBL463281.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082212572D          

 39 42  0  0  1  0            999 V2000
    0.0000   -1.6500    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


  Mrv1652309082212572D          

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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  6  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(O)C=CC=C2COC(=O)C2(O)C=CCCC2=O)[C@H](OC(=O)C2=CC=CC=C2)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O12/c28-13-18-20(31)21(32)23(38-24(33)15-7-2-1-3-8-15)25(37-18)39-22-16(9-6-10-17(22)29)14-36-26(34)27(35)12-5-4-11-19(27)30/h1-3,5-10,12,18,20-21,23,25,28-29,31-32,35H,4,11,13-14H2/t18-,20-,21+,23-,25+,27?/m1/s1

> <INCHI_KEY>
KAXLSURJPZQJPA-KELFPRCHSA-N

> <FORMULA>
C27H28O12

> <MOLECULAR_WEIGHT>
544.509

> <EXACT_MASS>
544.158076342

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.57803074048189

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate

> <JCHEM_LOGP>
1.759902107666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.409312836038083

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.586018209306948

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981093003865019

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
132.2116

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.152 -11.283   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.185 -11.283   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.175 -12.462   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.648 -13.909   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.132 -14.177   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.142 -12.997   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.625 -13.265   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   24                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24                                                            
CONECT   26    5   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    4   33                                                  
CONECT   33   32                                                            
CONECT   34    2   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   34                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₁₂

Average Mass

544.5090 Da

Monoisotopic Mass

544.15808 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C(O)C=CC=C2COC(=O)C2(O)C=CCCC2=O)[C@H](OC(=O)C2=CC=CC=C2)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H28O12/c28-13-18-20(31)21(32)23(38-24(33)15-7-2-1-3-8-15)25(37-18)39-22-16(9-6-10-17(22)29)14-36-26(34)27(35)12-5-4-11-19(27)30/h1-3,5-10,12,18,20-21,23,25,28-29,31-32,35H,4,11,13-14H2/t18-,20-,21+,23-,25+,27?/m1/s1

InChI Key

KAXLSURJPZQJPA-KELFPRCHSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Benzoate ester
Benzyloxycarbonyl
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
Cyclohexenone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Acyloin
Dicarboxylic acid or derivatives
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Alcohol
Organic oxide
Aldehyde
Carbonyl group
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

8545605

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10370160

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,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate (NP0266569)

MOL for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D MOL for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D SDF for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D-SDF for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

PDB for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D PDB for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

SMILES for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

INCHI for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

Structure for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)

3D Structure for NP0266569 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-2-{2-hydroxy-6-[(1-hydroxy-6-oxocyclohex-2-ene-1-carbonyloxy)methyl]phenoxy}-6-(hydroxymethyl)oxan-3-yl benzoate)