NP-MRD: Showing NP-Card for 4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one (NP0260064)

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Record Information

Version

2.0

Created at

2022-09-08 02:07:12 UTC

Updated at

2022-09-08 02:07:12 UTC

NP-MRD ID

NP0260064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one

Description

4-[(4R)-2,6,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one is found in Campanula medium. Based on a literature review very few articles have been published on 4-[(4R)-2,6,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082204072D          

 36 38  0  0  1  0            999 V2000
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6 34  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309082204072D          

 36 38  0  0  1  0            999 V2000
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   -3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873   -4.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -4.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  1  0  0  0
 10 33  1  0  0  0  0
 33 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260064

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H]3CC(C)=C(CCC(C)=O)C(C)(C)C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H42O11/c1-11-8-14(9-25(4,5)15(11)7-6-12(2)26)35-24-22(32)20(30)18(28)16(36-24)10-33-23-21(31)19(29)17(27)13(3)34-23/h13-14,16-24,27-32H,6-10H2,1-5H3/t13-,14+,16+,17-,18+,19+,20-,21+,22+,23+,24+/m0/s1

> <INCHI_KEY>
LJCQPTANBJCPLT-DKSDZHBRSA-N

> <FORMULA>
C25H42O11

> <MOLECULAR_WEIGHT>
518.6

> <EXACT_MASS>
518.272712172

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.97575999426881

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(4R)-2,6,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one

> <JCHEM_LOGP>
-0.6036796710000009

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.444318721819538

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.917414609330304

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121823516836606

> <JCHEM_POLAR_SURFACE_AREA>
175.37

> <JCHEM_REFRACTIVITY>
125.68120000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-[(4R)-2,6,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one

> <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  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0     -10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -13.337 -16.940   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.723  -7.880   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.723  -7.880   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   17   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   12   32                                                  
CONECT   32   31                                                            
CONECT   33   10   34                                                       
CONECT   34   33    6   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₂O₁₁

Average Mass

518.6000 Da

Monoisotopic Mass

518.27271 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H]3CC(C)=C(CCC(C)=O)C(C)(C)C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C25H42O11/c1-11-8-14(9-25(4,5)15(11)7-6-12(2)26)35-24-22(32)20(30)18(28)16(36-24)10-33-23-21(31)19(29)17(27)13(3)34-23/h13-14,16-24,27-32H,6-10H2,1-5H3/t13-,14+,16+,17-,18+,19+,20-,21+,22+,23+,24+/m0/s1

InChI Key

LJCQPTANBJCPLT-DKSDZHBRSA-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
Campanula medium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Megastigmane sesquiterpenoid
Sesquiterpenoid
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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

162994685

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one (NP0260064)

MOL for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

3D MOL for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

3D SDF for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

3D-SDF for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

PDB for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

3D PDB for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

SMILES for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

INCHI for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

Structure for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)

3D Structure for NP0260064 (4-[(4r)-2,6,6-trimethyl-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}cyclohex-1-en-1-yl]butan-2-one)