NP-MRD: Showing NP-Card for (2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone (NP0027278)

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Record Information

Version

1.0

Created at

2021-06-19 18:56:54 UTC

Updated at

2021-06-29 23:53:18 UTC

NP-MRD ID

NP0027278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone

Provided By

JEOL Database JEOL Logo

Description

(2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone is found in Streptomyces globisporus. It was first documented in 2004 (Rezanka, T., et al.). Based on a literature review very few articles have been published on (1S,2S,5S,6R,7S,10R,11S,14R,16R)-2,6,11,14-tetramethyl-5-propyl-4,13,19,20-tetraoxatricyclo[14.2.1.1⁷,¹⁰]Icosane-3,12-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120563D          

 67 69  0  0  0  0            999 V2000
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   -1.0688    5.1963   -1.5237 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.0813    2.2606   -4.5936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3915    1.4383   -2.7161 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 67 69  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192120563D          

 67 69  0  0  0  0            999 V2000
   -1.3758    6.6859   -1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0688    5.1963   -1.5237 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0027278

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])C([H])([H])C([H])([H])[C@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])[C@@]2([H])O[C@]([H])(C([H])([H])C2([H])[H])C([H])([H])[C@]([H])(OC(=O)[C@@]([H])(C([H])([H])[H])[C@]2([H])O[C@@]([H])(C([H])([H])C2([H])[H])[C@@]1([H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H38O6/c1-6-7-18-14(3)19-10-11-21(28-19)16(5)22(24)26-13(2)12-17-8-9-20(27-17)15(4)23(25)29-18/h13-21H,6-12H2,1-5H3/t13-,14+,15+,16+,17-,18+,19+,20+,21-/m1/s1

> <INCHI_KEY>
TUEIVMZOUQSYJA-XFHAOOBSSA-N

> <FORMULA>
C23H38O6

> <MOLECULAR_WEIGHT>
410.551

> <EXACT_MASS>
410.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
46.27142950586208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,6R,7S,10R,11S,14R,16R)-2,6,11,14-tetramethyl-5-propyl-4,13,19,20-tetraoxatricyclo[14.2.1.1^{7,10}]icosane-3,12-dione

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
4.163949101333332

> <ALOGPS_LOGS>
-4.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.871984621026082

> <JCHEM_POLAR_SURFACE_AREA>
71.06000000000002

> <JCHEM_REFRACTIVITY>
108.2148

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,6R,7S,10R,11S,14R,16R)-2,6,11,14-tetramethyl-5-propyl-4,13,19,20-tetraoxatricyclo[14.2.1.1^{7,10}]icosane-3,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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  3 36  1  0
 27 64  1  1
 28 65  1  0
 28 66  1  0
 28 67  1  0
 25 63  1  6
 24 61  1  0
 24 62  1  0
 23 59  1  0
 23 60  1  0
 22 58  1  1
 20 54  1  6
 21 55  1  0
 21 56  1  0
 21 57  1  0
 14 48  1  0
 14 49  1  0
 15 50  1  1
 16 51  1  0
 16 52  1  0
 16 53  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.376   6.686  -1.560  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.069   5.196  -1.524  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.514   4.710  -2.869  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.128   3.218  -2.892  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.291   2.474  -2.451  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.193   2.080  -3.389  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.081   2.261  -4.594  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.392   1.438  -2.716  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.595   2.348  -2.958  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.575   0.019  -3.256  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.899  -0.632  -2.887  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.575  -2.094  -3.057  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.128  -2.187  -2.578  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.030  -2.685  -1.125  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.612  -3.031  -0.626  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.933  -4.084  -1.501  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.830  -1.825  -0.575  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.306  -1.845   0.179  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.714  -2.807   0.814  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.993  -0.499   0.101  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.640  -0.165   1.448  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.031  -0.464  -1.037  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.530  -0.892  -2.409  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.766   0.333  -2.842  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.684   1.452  -2.370  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.421   0.918  -1.237  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.044   2.805  -1.962  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.170   3.850  -1.896  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.579  -0.860  -2.689  0.00  0.00           O+0
HETATM   30  H   UNK     0      -0.472   7.267  -1.766  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.116   6.915  -2.333  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.778   7.013  -0.596  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.357   5.001  -0.716  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.989   4.654  -1.278  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.294   4.873  -3.624  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.338   5.327  -3.177  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.135   2.949  -3.923  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.197   1.390  -1.637  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.369   3.379  -2.663  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.876   2.363  -4.017  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.463   2.022  -2.378  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.441  -0.009  -4.345  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.729  -0.304  -3.519  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.156  -0.433  -1.840  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.266  -2.756  -2.526  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.624  -2.355  -4.121  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.573  -2.848  -3.250  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.654  -3.580  -1.012  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.437  -1.909  -0.464  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.718  -3.424   0.393  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.644  -3.675  -2.474  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.583  -4.950  -1.656  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.008  -4.440  -1.037  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.223   0.268  -0.052  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.054   0.848   1.444  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.903  -0.225   2.257  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.449  -0.863   1.687  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.921  -1.040  -0.760  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.383  -1.041  -3.082  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.940  -1.808  -2.423  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.578   0.365  -3.919  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.194   0.345  -2.325  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.430   1.629  -3.156  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.655   2.689  -0.941  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.005   3.492  -1.283  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.831   4.786  -1.443  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.558   4.074  -2.895  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1   33   34                                             
CONECT    3    4    2   35   36                                             
CONECT    4    5    3   27   37                                             
CONECT    5    6    4                                                       
CONECT    6    8    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9    6   10   38                                             
CONECT    9    8   39   40   41                                             
CONECT   10   29    8   11   42                                             
CONECT   11   12   10   43   44                                             
CONECT   12   13   11   45   46                                             
CONECT   13   12   29   14   47                                             
CONECT   14   15   13   48   49                                             
CONECT   15   14   16   17   50                                             
CONECT   16   15   51   52   53                                             
CONECT   17   18   15                                                       
CONECT   18   20   19   17                                                  
CONECT   19   18                                                            
CONECT   20   21   18   22   54                                             
CONECT   21   20   55   56   57                                             
CONECT   22   26   20   23   58                                             
CONECT   23   24   22   59   60                                             
CONECT   24   25   23   61   62                                             
CONECT   25   24   26   27   63                                             
CONECT   26   22   25                                                       
CONECT   27    4   28   25   64                                             
CONECT   28   27   65   66   67                                             
CONECT   29   10   13                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   16                                                            
CONECT   52   16                                                            
CONECT   53   16                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   21                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   24                                                            
CONECT   63   25                                                            
CONECT   64   27                                                            
CONECT   65   28                                                            
CONECT   66   28                                                            
CONECT   67   28                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  138    0
END

RDKit          3D

67 69  0  0  0  0  0  0  0  0999 V2000
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 10  8  1  0
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  3  2  1  0
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  2  1  1  0
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 13 47  1  6
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 12 46  1  0
 11 43  1  0
 11 44  1  0
 10 42  1  6
  8 38  1  1
  9 39  1  0
  9 40  1  0
  9 41  1  0
  4 37  1  6
  3 35  1  0
  3 36  1  0
 27 64  1  1
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 16 52  1  0
 16 53  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
Nonactate-trihomononactate dilactone	Generator

Chemical Formula

C₂₃H₃₈O₆

Average Mass

410.5510 Da

Monoisotopic Mass

410.26684 Da

IUPAC Name

(1S,2S,5S,6R,7S,10R,11S,14R,16R)-2,6,11,14-tetramethyl-5-propyl-4,13,19,20-tetraoxatricyclo[14.2.1.1^{7,10}]icosane-3,12-dione

Traditional Name

(1S,2S,5S,6R,7S,10R,11S,14R,16R)-2,6,11,14-tetramethyl-5-propyl-4,13,19,20-tetraoxatricyclo[14.2.1.1^{7,10}]icosane-3,12-dione

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])C([H])([H])C([H])([H])[C@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])[C@@]2([H])O[C@]([H])(C([H])([H])C2([H])[H])C([H])([H])[C@]([H])(OC(=O)[C@@]([H])(C([H])([H])[H])[C@]2([H])O[C@@]([H])(C([H])([H])C2([H])[H])[C@@]1([H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H38O6/c1-6-7-18-14(3)19-10-11-21(28-19)16(5)22(24)26-13(2)12-17-8-9-20(27-17)15(4)23(25)29-18/h13-21H,6-12H2,1-5H3/t13-,14+,15+,16+,17-,18+,19+,20+,21-/m1/s1

InChI Key

TUEIVMZOUQSYJA-XFHAOOBSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, NULL, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces globisporus	JEOL database	Rezanka, T., et al, J. Org. Chem. 2004, 4239

Chemical Taxonomy

Classification

Not classified

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	3.74	ALOGPS
logP	4.16	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.21 m³·mol⁻¹	ChemAxon
Polarizability	46.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

9352443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11177351

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rezanka, T., et al. (2004). Rezanka, T., et al, J. Org. Chem. 2004, 4239. J. Org. Chem..

Showing NP-Card for (2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone (NP0027278)

MOL for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

3D MOL for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

3D SDF for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

3D-SDF for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

PDB for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

3D PDB for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

SMILES for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

INCHI for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

Structure for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)

3D Structure for NP0027278 ((2S,3R,6S,7R,8S,2'S,3'S,6'R,8'R)-dilactone)