NP-MRD: Showing NP-Card for scupolin I (NP0040939)

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Record Information

Version

2.0

Created at

2021-06-20 22:58:29 UTC

Updated at

2021-06-30 00:15:10 UTC

NP-MRD ID

NP0040939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

scupolin I

Provided By

JEOL Database JEOL Logo

Description

scupolin I is found in Lagochilus leiacanthus (Labiatae). scupolin I was first documented in 2011 (Furukaewa, M., et al.). Based on a literature review very few articles have been published on (1'R,2R,2'S,4'R,5'S,6'R,8'R,11'S)-5'-[(2S,3aS,5R,6aR)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-11'-methoxy-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0¹,⁶]Dodecane]-2'-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100583D          

 68 73  0  0  0  0            999 V2000
   -3.6043    4.9994    5.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0072    4.2128    4.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293    2.8297    4.4485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2812    2.0442    3.2753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1895    2.2309    2.2373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9095    1.0296    1.3647 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9592    0.2019    2.2270 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0557   -0.8710    1.5011 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.9732   -1.8314    0.6553 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.6157    0.5006   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 35  1  0  0  0  0
M  END

     RDKit          3D

 68 73  0  0  0  0  0  0  0  0999 V2000
   -3.6043    4.9994    5.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0072    4.2128    4.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212100583D          

 68 73  0  0  0  0            999 V2000
   -3.6043    4.9994    5.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0040939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])O[C@]1([H])O[C@@]2([H])O[C@@]([H])(C([H])([H])[C@@]2([H])C1([H])[H])[C@@]1(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]23[C@@]([H])(OC([H])([H])[H])O[C@]([H])(C([H])([H])[C@]12[H])C([H])([H])[C@@]31OC1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O8/c1-12-6-18(29-13(2)25)24-16(9-15(30-21(24)27-5)10-23(24)11-28-23)22(12,3)17-7-14-8-19(26-4)32-20(14)31-17/h12,14-21H,6-11H2,1-5H3/t12-,14+,15-,16-,17+,18+,19-,20-,21+,22+,23+,24+/m1/s1

> <INCHI_KEY>
JABSDRHNLBFGDC-QWKXYRIXSA-N

> <FORMULA>
C24H36O8

> <MOLECULAR_WEIGHT>
452.544

> <EXACT_MASS>
452.241018119

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
48.00772408260822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2R,2'S,4'R,5'S,6'R,8'R,11'S)-5'-[(2S,3aS,5R,6aR)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-11'-methoxy-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0^{1,6}]dodecane]-2'-yl acetate

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.8503027896666653

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.547608814393262

> <JCHEM_POLAR_SURFACE_AREA>
84.98000000000002

> <JCHEM_REFRACTIVITY>
110.88119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'S,4'R,5'S,6'R,8'R,11'S)-5'-[(2S,3aS,5R,6aR)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-11'-methoxy-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0^{1,6}]dodecane]-2'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 73  0  0  0  0  0  0  0  0999 V2000
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 28 29  1  0
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 18 27  1  0
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M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.604   4.999   5.356  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.007   4.213   4.242  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.729   2.830   4.449  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.281   2.044   3.275  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.189   2.231   2.237  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.910   1.030   1.365  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.959   0.202   2.227  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.056  -0.871   1.501  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.355  -1.673   2.632  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.973  -1.831   0.655  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.985  -2.645   1.477  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.167  -2.797  -0.225  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.285  -2.048  -1.223  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.389  -3.034  -2.023  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.133  -3.295  -3.250  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.765  -4.236  -3.993  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.186  -2.852  -3.689  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.723  -1.100  -0.534  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.928  -1.850   0.143  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.763  -2.479  -0.833  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.750  -3.313  -0.246  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.719  -0.950   0.938  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.454   0.426   0.635  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.059   0.733   1.192  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.011  -0.180   0.526  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.522   0.668  -0.881  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.374  -0.080  -1.510  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.659   0.543  -2.699  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.604  -0.520  -2.854  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.178   1.166   2.946  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.934   2.374   3.079  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.325   2.581   4.436  0.00  0.00           O+0
HETATM   33  H   UNK     0      -4.130   4.682   6.262  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.522   4.938   5.505  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.866   6.041   5.151  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.167   2.493   5.395  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.249   2.413   2.923  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.391   0.989   3.549  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.388   3.133   1.647  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.814   0.485   1.081  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.423   1.376   0.449  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.556  -0.312   2.991  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.386  -1.085   3.178  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.079  -2.009   3.383  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.141  -2.574   2.271  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.564  -1.211  -0.032  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.490  -3.361   2.141  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.634  -2.004   2.078  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.639  -3.220   0.811  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.856  -3.440  -0.789  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.569  -3.492   0.376  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.955  -1.448  -1.848  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.367  -4.398  -4.999  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.807  -5.196  -3.473  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.764  -3.801  -4.083  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.561  -2.632   0.809  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.318  -3.788  -1.051  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.444  -2.729   0.365  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.285  -4.099   0.356  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.208   1.031   1.147  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.809   1.786   1.014  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.097   0.598   2.275  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.616   0.501  -0.089  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.474   0.300  -1.279  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.447   1.741  -1.092  0.00  0.00           H+0
HETATM   66  H   UNK     0       0.962   1.526  -3.041  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.382   0.324  -2.898  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.305   3.210   2.755  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    3    1                                                       
CONECT    3    4   32    2   36                                             
CONECT    4    5    3   37   38                                             
CONECT    5    4   39   31    6                                             
CONECT    6    7    5   40   41                                             
CONECT    7   30    6    8   42                                             
CONECT    8   25    9   10    7                                             
CONECT    9    8   43   44   45                                             
CONECT   10   12   11    8   46                                             
CONECT   11   10   47   48   49                                             
CONECT   12   10   13   50   51                                             
CONECT   13   14   18   12   52                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   53   54   55                                             
CONECT   17   15                                                            
CONECT   18   27   19   13   25                                             
CONECT   19   18   20   22   56                                             
CONECT   20   19   21                                                       
CONECT   21   20   57   58   59                                             
CONECT   22   23   19                                                       
CONECT   23   24   26   22   60                                             
CONECT   24   25   23   61   62                                             
CONECT   25    8   24   63   18                                             
CONECT   26   23   27   64   65                                             
CONECT   27   18   26   28   29                                             
CONECT   28   29   27   66   67                                             
CONECT   29   28   27                                                       
CONECT   30   31    7                                                       
CONECT   31   68   32    5   30                                             
CONECT   32    3   31                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41    6                                                            
CONECT   42    7                                                            
CONECT   43    9                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   12                                                            
CONECT   52   13                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   16                                                            
CONECT   56   19                                                            
CONECT   57   21                                                            
CONECT   58   21                                                            
CONECT   59   21                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   24                                                            
CONECT   63   25                                                            
CONECT   64   26                                                            
CONECT   65   26                                                            
CONECT   66   28                                                            
CONECT   67   28                                                            
CONECT   68   31                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  146    0
END

RDKit          3D

68 73  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Value	Source
(1'r,2R,2's,4'r,5's,6'r,8'r,11's)-5'-[(2S,3AS,5R,6ar)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-11'-methoxy-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0,]dodecane]-2'-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₆O₈

Average Mass

452.5440 Da

Monoisotopic Mass

452.24102 Da

IUPAC Name

(1'R,2R,2'S,4'R,5'S,6'R,8'R,11'S)-5'-[(2S,3aS,5R,6aR)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-11'-methoxy-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0^{1,6}]dodecane]-2'-yl acetate

Traditional Name

(1'R,2R,2'S,4'R,5'S,6'R,8'R,11'S)-5'-[(2S,3aS,5R,6aR)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-11'-methoxy-4',5'-dimethyl-12'-oxaspiro[oxirane-2,10'-tricyclo[6.2.2.0^{1,6}]dodecane]-2'-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])O[C@]1([H])O[C@@]2([H])O[C@@]([H])(C([H])([H])[C@@]2([H])C1([H])[H])[C@@]1(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]23[C@@]([H])(OC([H])([H])[H])O[C@]([H])(C([H])([H])[C@]12[H])C([H])([H])[C@@]31OC1([H])[H]

InChI Identifier

InChI=1S/C24H36O8/c1-12-6-18(29-13(2)25)24-16(9-15(30-21(24)27-5)10-23(24)11-28-23)22(12,3)17-7-14-8-19(26-4)32-20(14)31-17/h12,14-21H,6-11H2,1-5H3/t12-,14+,15-,16-,17+,18+,19-,20-,21+,22+,23+,24+/m1/s1

InChI Key

JABSDRHNLBFGDC-QWKXYRIXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Lagochilus leiacanthus (Labiatae)	JEOL database	Furukaewa, M., et al, Chem. Pharm. Bull. 59, 1535 (2011)

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	2.01	ALOGPS
logP	1.85	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	84.98 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	110.88 m³·mol⁻¹	ChemAxon
Polarizability	48.01 Å³	ChemAxon
Number of Rings	6	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

8703022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10527626

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Furukaewa, M., et al. (2011). Furukaewa, M., et al, Chem. Pharm. Bull. 59, 1535 (2011). Chem. Pharm. Bull..

Showing NP-Card for scupolin I (NP0040939)

MOL for NP0040939 (scupolin I)

3D MOL for NP0040939 (scupolin I)

3D SDF for NP0040939 (scupolin I)

3D-SDF for NP0040939 (scupolin I)

PDB for NP0040939 (scupolin I)

3D PDB for NP0040939 (scupolin I)

SMILES for NP0040939 (scupolin I)

INCHI for NP0040939 (scupolin I)

Structure for NP0040939 (scupolin I)

3D Structure for NP0040939 (scupolin I)