NP-MRD: Showing NP-Card for Neobulgarone C/D (NP0003574)

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Record Information

Version

1.0

Created at

2020-12-09 00:47:16 UTC

Updated at

2021-07-15 16:46:47 UTC

NP-MRD ID

NP0003574

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neobulgarone C/D

Provided By

NPAtlas

Description

1-Chloro-2,2',4,4'-tetrahydroxy-5,5'-dimethoxy-7,7'-dimethyl-9H,9'H,10H,10'H-[9,9'-bianthracene]-10,10'-dione belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. Neobulgarone C/D is found in Neobulgaria pura and Neobulgaria pura HA A07-97. It was first documented in 2000 (PMID: 11132957). Based on a literature review very few articles have been published on 1-chloro-2,2',4,4'-tetrahydroxy-5,5'-dimethoxy-7,7'-dimethyl-9H,9'H,10H,10'H-[9,9'-bianthracene]-10,10'-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 66 71  0  0  0  0            999 V2000
   -6.6336   -0.0343   -1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4478   -0.4296   -0.5967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1866    0.0367   -1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9364    2.3108   -3.6611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7938    0.9659   -1.8599 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1276   -1.2439    0.7516 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 66 71  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117483D          

 66 71  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0003574

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(=O)C3=C(C([H])=C(C([H])=C3OC([H])([H])[H])C([H])([H])[H])[C@]([H])(C2=C1[H])[C@]1([H])C2=C([H])C(=C([H])C(OC([H])([H])[H])=C2C(=O)C2=C(O[H])C([H])=C(O[H])C(Cl)=C12)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C32H25ClO8/c1-12-5-15-23(17-9-14(34)10-18(35)24(17)31(38)25(15)21(7-12)40-3)27-16-6-13(2)8-22(41-4)26(16)32(39)28-19(36)11-20(37)30(33)29(27)28/h5-11,23,27,34-37H,1-4H3/t23-,27+/m1/s1

> <INCHI_KEY>
XTZHVTOVVQVQKP-UHFFFAOYSA-N

> <FORMULA>
C32H25ClO8

> <MOLECULAR_WEIGHT>
572.99

> <EXACT_MASS>
572.1237955

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
59.203491472851375

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,9'R)-1-chloro-2,2',4,4'-tetrahydroxy-5,5'-dimethoxy-7,7'-dimethyl-9H,9'H,10H,10'H-[9,9'-bianthracene]-10,10'-dione

> <ALOGPS_LOGP>
5.26

> <JCHEM_LOGP>
7.724752725666666

> <ALOGPS_LOGS>
-5.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.838835146135243

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.402778363880522

> <JCHEM_PKA_STRONGEST_BASIC>
-4.575764207865246

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
154.45559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R,9'R)-1-chloro-2,2',4,4'-tetrahydroxy-5,5'-dimethoxy-7,7'-dimethyl-9H,9'H-[9,9'-bianthracene]-10,10'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 71  0  0  0  0  0  0  0  0999 V2000
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 29 62  1  0
 29 63  1  0
 35 64  1  0
 36 65  1  0
 38 66  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.634  -0.034  -1.233  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.448  -0.430  -0.597  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.187   0.037  -1.014  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.180   0.910  -2.090  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.968   1.370  -2.505  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.936   2.311  -3.661  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.794   0.966  -1.860  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.807   0.091  -0.783  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.033  -0.352  -0.389  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.128  -1.244   0.752  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.230  -1.675   1.155  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.900  -1.650   1.449  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.058  -2.496   2.530  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.310  -2.933   2.929  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.951  -2.910   3.222  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.283  -2.477   2.824  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.393  -2.903   3.531  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.406  -1.622   1.726  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.678  -1.187   1.013  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.502  -0.320  -0.158  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.491   0.779  -0.069  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.728   0.288  -0.767  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.609  -0.227  -2.058  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.687  -0.720  -2.774  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.467  -1.252  -4.148  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.940  -0.710  -2.203  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.093  -0.207  -0.926  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.330  -0.182  -0.327  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.496  -0.649  -0.942  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.975   0.281  -0.241  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.196   0.819   1.091  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.385   0.792   1.554  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.063   1.360   1.828  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.350   1.895   3.068  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.558   1.938   3.699  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.265   2.465   3.765  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.019   2.471   3.216  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.052   3.044   3.923  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.244   1.924   1.964  0.00  0.00           C+0
HETATM   40 Cl   UNK     0      -1.891   2.091   1.406  0.00  0.00          Cl+0
HETATM   41  C   UNK     0       0.781   1.359   1.257  0.00  0.00           C+0
HETATM   42  H   UNK     0      -7.488  -0.535  -0.759  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.814   1.051  -1.201  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.582  -0.420  -2.286  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.122   1.182  -2.545  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.241   3.330  -3.369  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.872   2.399  -4.018  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.502   1.924  -4.528  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.913   1.404  -2.287  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.404  -3.545   3.714  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.076  -3.587   4.088  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.919  -3.741   3.314  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.425  -1.355   1.477  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.138  -1.092  -0.959  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.155   1.688  -0.675  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.664  -0.266  -2.562  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.799  -2.146  -4.100  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.880  -0.472  -4.704  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.415  -1.462  -4.647  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.785  -1.087  -2.742  0.00  0.00           H+0
HETATM   61  H   UNK     0       6.762   0.063  -1.755  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.383  -1.660  -1.395  0.00  0.00           H+0
HETATM   63  H   UNK     0       7.318  -0.619  -0.214  0.00  0.00           H+0
HETATM   64  H   UNK     0       4.410   1.616   3.421  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.494   2.887   4.745  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.845   3.434   4.828  0.00  0.00           H+0
CONECT    1    2   42   43   44                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   45                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   46   47   48                                             
CONECT    7    5    8   49                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   50                                                       
CONECT   15   13   16   51                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   52                                                       
CONECT   18   16   19   53                                                  
CONECT   19   18   20   12                                                  
CONECT   20   19   21    8   54                                             
CONECT   21   20   22   41   55                                             
CONECT   22   21   23   30                                                  
CONECT   23   22   24   56                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   57   58   59                                             
CONECT   26   24   27   60                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   61   62   63                                             
CONECT   30   27   31   22                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   41                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34   64                                                       
CONECT   36   34   37   65                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37   66                                                       
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   21   33                                                  
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    4                                                            
CONECT   46    6                                                            
CONECT   47    6                                                            
CONECT   48    6                                                            
CONECT   49    7                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   17                                                            
CONECT   53   18                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   23                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
CONECT   63   29                                                            
CONECT   64   35                                                            
CONECT   65   36                                                            
CONECT   66   38                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  142    0
END

RDKit          3D

66 71  0  0  0  0  0  0  0  0999 V2000
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    6.3828   -1.6601   -1.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4939    2.8867    4.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446    3.4345    4.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
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 31 33  1  0
 33 34  2  0
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 36 37  2  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  2  0
  9  3  1  0
 19 12  1  0
 41 21  1  0
 20  8  1  0
 30 22  1  0
 41 33  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  6 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
 14 50  1  0
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 29 61  1  0
 29 62  1  0
 29 63  1  0
 35 64  1  0
 36 65  1  0
 38 66  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₂H₂₅ClO₈

Average Mass

572.9900 Da

Monoisotopic Mass

572.12380 Da

IUPAC Name

(9R,9'R)-1-chloro-2,2',4,4'-tetrahydroxy-5,5'-dimethoxy-7,7'-dimethyl-9H,9'H,10H,10'H-[9,9'-bianthracene]-10,10'-dione

Traditional Name

(9R,9'R)-1-chloro-2,2',4,4'-tetrahydroxy-5,5'-dimethoxy-7,7'-dimethyl-9H,9'H-[9,9'-bianthracene]-10,10'-dione

CAS Registry Number

Not Available

SMILES

COC1=C2C(=O)C3=C(O)C=C(O)C=C3C(C3C4=CC(C)=CC(OC)=C4C(=O)C4=C3C(Cl)=C(O)C=C4O)C2=CC(C)=C1

InChI Identifier

InChI=1S/C32H25ClO8/c1-12-5-15-23(17-9-14(34)10-18(35)24(17)31(38)25(15)21(7-12)40-3)27-16-6-13(2)8-22(41-4)26(16)32(39)28-19(36)11-20(37)30(33)29(27)28/h5-11,23,27,34-37H,1-4H3

InChI Key

XTZHVTOVVQVQKP-UHFFFAOYSA-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
Neobulgaria pura	NPAtlas	11132957
Neobulgaria pura HA A07-97	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Anisole
Aryl ketone
Phenol ether
4-halophenol
2-halophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Aryl chloride
Aryl halide
Vinylogous acid
Ketone
Ether
Organohalogen compound
Organochloride
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.26	ALOGPS
logP	7.72	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	154.46 m³·mol⁻¹	ChemAxon
Polarizability	59.2 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002124

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85192835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Eilbert F, Anke H, Sterner O: Neobulgarones A approximately F from cultures of Neobulgaria pura, new inhibitors of appressorium formation of Magnaporthe grisea. J Antibiot (Tokyo). 2000 Oct;53(10):1123-9. doi: 10.7164/antibiotics.53.1123. [PubMed:11132957 ]

Showing NP-Card for Neobulgarone C/D (NP0003574)

MOL for NP0003574 (Neobulgarone C/D)

3D MOL for NP0003574 (Neobulgarone C/D)

3D SDF for NP0003574 (Neobulgarone C/D)

3D-SDF for NP0003574 (Neobulgarone C/D)

PDB for NP0003574 (Neobulgarone C/D)

3D PDB for NP0003574 (Neobulgarone C/D)

SMILES for NP0003574 (Neobulgarone C/D)

INCHI for NP0003574 (Neobulgarone C/D)

Structure for NP0003574 (Neobulgarone C/D)

3D Structure for NP0003574 (Neobulgarone C/D)