NP-MRD: Showing NP-Card for (-)-Renillin A (NP0078686)

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Record Information

Version

2.0

Created at

2022-04-28 23:42:37 UTC

Updated at

2022-04-28 23:42:37 UTC

NP-MRD ID

NP0078686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Renillin A

Description

(1S,2R,3R,4R,7R,8S,10E,12S,13S,16S,17S)-2-(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-12-(propanoyloxy)-6-oxatricyclo[11.4.0.0³,⁷]Heptadec-10-en-16-yl butanoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (-)-Renillin A is found in Renilla reniformis. Based on a literature review very few articles have been published on (1S,2R,3R,4R,7R,8S,10E,12S,13S,16S,17S)-2-(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-12-(propanoyloxy)-6-oxatricyclo[11.4.0.0³,⁷]Heptadec-10-en-16-yl butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201422D          

 40 42  0  0  1  0            999 V2000
   -3.2896    7.9460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5752    8.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5752    9.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1462    8.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    7.9460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4317    7.1210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1462    6.7085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.2896    7.1210    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.0041    8.3585    0.0000 Cl  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  2  0  0  0  0
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  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  1 11  1  0  0  0  0
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 15 16  1  1  0  0  0
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  9 18  1  6  0  0  0
 18 19  1  0  0  0  0
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  8 22  1  0  0  0  0
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  7 25  1  0  0  0  0
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  7 34  1  6  0  0  0
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 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 40  1  1  0  0  0
M  END

     RDKit          3D

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 23 66  1  0
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M  END


  Mrv1652304292201422D          

 40 42  0  0  1  0            999 V2000
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   -0.4317    4.6460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    4.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    3.4085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972    4.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7117    4.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261    4.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963    5.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834    5.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    7.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    8.3585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2827    9.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    9.5960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972    9.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   10.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0041    8.3585    0.0000 Cl  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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  1  0  0  0
 10 17  1  1  0  0  0
  9 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
 23 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 22 32  1  6  0  0  0
 22 33  1  1  0  0  0
  7 34  1  6  0  0  0
  6 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@H]1CC[C@@]2(C)[C@@H]([C@@H](OC(C)=O)[C@]3(O)[C@@H](C)C(=O)O[C@H]3[C@@H](Cl)C(=C)\C=C\[C@@H]2OC(=O)CC)[C@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C29H41ClO10/c1-8-10-21(33)39-19-13-14-27(6)18(38-20(32)9-2)12-11-15(3)22(30)24-29(36,16(4)26(34)40-24)25(37-17(5)31)23(27)28(19,7)35/h11-12,16,18-19,22-25,35-36H,3,8-10,13-14H2,1-2,4-7H3/b12-11+/t16-,18-,19-,22-,23+,24-,25+,27+,28+,29-/m0/s1

> <INCHI_KEY>
FSOSFMPSMUWBAF-DOTQWUFXSA-N

> <FORMULA>
C29H41ClO10

> <MOLECULAR_WEIGHT>
585.09

> <EXACT_MASS>
584.2388252

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
61.151460148003665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4R,7R,8S,10E,12S,13S,16S,17S)-2-(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-12-(propanoyloxy)-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-16-yl butanoate

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.1005051223333338

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.726738439742203

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.348091894909423

> <JCHEM_PKA_STRONGEST_BASIC>
-3.367144444376412

> <JCHEM_POLAR_SURFACE_AREA>
145.66000000000003

> <JCHEM_REFRACTIVITY>
142.9959

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4R,7R,8S,10E,12S,13S,16S,17S)-2-(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-12-(propanoyloxy)-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-16-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -6.141  14.833   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.807  15.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.807  17.143   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.473  14.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.140  15.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.806  14.833   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.806  13.293   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.140  12.523   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.473  13.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.807  12.523   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.141  13.293   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.285  12.262   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -6.659  10.855   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -7.429   9.522   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.933  10.917   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.097   9.872   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.561  11.617   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.997  11.828   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.028  10.684   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.552   9.219   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.534  11.004   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.140  10.983   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.806  10.213   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.528  10.983   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.528  12.523   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.806   8.673   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.528   7.903   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.528   6.363   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.861   8.673   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.195   7.903   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.529   8.673   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.353  10.034   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.956   9.677   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.528  14.063   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.528  15.603   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.528  17.143   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.806  17.913   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.861  17.913   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.861  19.453   0.000  0.00  0.00           C+0
HETATM   40 Cl   UNK     0      -7.474  15.603   0.000  0.00  0.00          Cl+0
CONECT    1    2   11   40                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8   25   34                                             
CONECT    8    7    9   22                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   15   17                                             
CONECT   11   10    1   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10   16                                                  
CONECT   16   15                                                            
CONECT   17   10                                                            
CONECT   18    9   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    8   23   32   33                                             
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24    7                                                       
CONECT   26   23   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   22                                                            
CONECT   33   22                                                            
CONECT   34    7                                                            
CONECT   35    6   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,4R,7R,8S,10E,12S,13S,16S,17S)-2-(Acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-12-(propanoyloxy)-6-oxatricyclo[11.4.0.0,]heptadec-10-en-16-yl butanoic acid	Generator

Chemical Formula

C₂₉H₄₁ClO₁₀

Average Mass

585.0900 Da

Monoisotopic Mass

584.23883 Da

IUPAC Name

(1S,2R,3R,4R,7R,8S,10E,12S,13S,16S,17S)-2-(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-12-(propanoyloxy)-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-16-yl butanoate

Traditional Name

(1S,2R,3R,4R,7R,8S,10E,12S,13S,16S,17S)-2-(acetyloxy)-8-chloro-3,17-dihydroxy-4,13,17-trimethyl-9-methylidene-5-oxo-12-(propanoyloxy)-6-oxatricyclo[11.4.0.0^{3,7}]heptadec-10-en-16-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@H]1CC[C@@]2(C)[C@@H]([C@@H](OC(C)=O)[C@]3(O)[C@@H](C)C(=O)O[C@H]3[C@@H](Cl)C(=C)\C=C\[C@@H]2OC(=O)CC)[C@]1(C)O

InChI Identifier

InChI=1S/C29H41ClO10/c1-8-10-21(33)39-19-13-14-27(6)18(38-20(32)9-2)12-11-15(3)22(30)24-29(36,16(4)26(34)40-24)25(37-17(5)31)23(27)28(19,7)35/h11-12,16,18-19,22-25,35-36H,3,8-10,13-14H2,1-2,4-7H3/b12-11+/t16-,18-,19-,22-,23+,24-,25+,27+,28+,29-/m0/s1

InChI Key

FSOSFMPSMUWBAF-DOTQWUFXSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Renilla reniformis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Briarane diterpenoid
Diterpenoid
Diterpene lactone
Tetracarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.13	ALOGPS
logP	3.1	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	143 m³·mol⁻¹	ChemAxon
Polarizability	61.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

163104039

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Renillin A (NP0078686)

MOL for NP0078686 ((-)-Renillin A)

3D MOL for NP0078686 ((-)-Renillin A)

3D SDF for NP0078686 ((-)-Renillin A)

3D-SDF for NP0078686 ((-)-Renillin A)

PDB for NP0078686 ((-)-Renillin A)

3D PDB for NP0078686 ((-)-Renillin A)

SMILES for NP0078686 ((-)-Renillin A)

INCHI for NP0078686 ((-)-Renillin A)

Structure for NP0078686 ((-)-Renillin A)

3D Structure for NP0078686 ((-)-Renillin A)