NP-MRD: Showing NP-Card for Botcineric acid (NP0006330)

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Record Information

Version

2.0

Created at

2020-12-09 03:22:34 UTC

Updated at

2021-07-15 16:54:29 UTC

NP-MRD ID

NP0006330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Botcineric acid

Provided By

NPAtlas

Description

Botcineric acid is also known as botcinerate or homobotcinolide. Botcineric acid is found in Botrytis cinerea. Botcineric acid was first documented in 2006 (PMID: 16643065). Based on a literature review very few articles have been published on Botcineric acid (PMID: 19137164).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118273D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242118273D          

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 29 14  1  0  0  0  0
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  3 36  1  0  0  0  0
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 30 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])[C@]1(O[C@@]([H])(C([H])([H])[H])[C@]([H])(OC(=O)C(\[H])=C(/[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])[C@]1([H])O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H38O8/c1-6-7-8-9-10-16(23)11-12-17(24)29-18-13(2)19(25)22(5,30-15(18)4)20(26)14(3)21(27)28/h11-16,18-20,23,25-26H,6-10H2,1-5H3,(H,27,28)/b12-11+/t13-,14-,15+,16+,18-,19+,20+,22+/m1/s1

> <INCHI_KEY>
CIZAXJJDWVUEEL-AFQFPRFFSA-N

> <FORMULA>
C22H38O8

> <MOLECULAR_WEIGHT>
430.538

> <EXACT_MASS>
430.256668184

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
47.28898134394815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-3-hydroxy-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(2E,4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.8701917183333316

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.367418671664876

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.104583319950775

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8715617686901487

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
110.89269999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-3-hydroxy-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(2E,4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 68  0  0  0  0  0  0  0  0999 V2000
    8.4020    2.2008    1.1937 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8847    1.0587    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0883   -0.2036    0.6775 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7988   -0.8262   -2.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445   -0.7437   -2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2587   -0.5377   -1.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
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 10 47  1  0
 14 48  1  6
 15 49  1  1
 16 50  1  0
 16 51  1  0
 16 52  1  0
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 19 54  1  0
 19 55  1  0
 20 56  1  6
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 23 61  1  0
 26 62  1  0
 27 63  1  6
 28 64  1  0
 29 65  1  1
 30 66  1  0
 30 67  1  0
 30 68  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       8.402   2.201   1.194  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.885   1.059   0.347  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.088  -0.204   0.678  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.598   0.052   0.393  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.792  -1.167   0.707  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.319  -1.022   0.503  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.931  -0.697  -0.892  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.470   0.505  -1.306  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.448  -0.630  -0.986  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.799  -0.826  -2.120  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.345  -0.744  -2.129  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.318  -0.923  -3.189  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.347  -0.468  -0.980  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.754  -0.369  -0.895  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.182  -1.437   0.124  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.671  -2.772  -0.360  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.542  -1.437   0.128  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.166  -0.309   0.630  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.189  -0.459   2.142  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.569  -0.366   0.061  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.210  -1.549   0.468  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.431   0.803   0.360  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.781   0.504  -0.330  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.780   0.965   1.795  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.439   2.037   2.400  0.00  0.00           O+0
HETATM   26  O   UNK     0      -7.454   0.029   2.525  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.550   0.981   0.242  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.557   1.868   1.325  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.127   0.932  -0.239  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.835   2.133  -1.108  0.00  0.00           C+0
HETATM   31  H   UNK     0       9.284   2.772   1.549  0.00  0.00           H+0
HETATM   32  H   UNK     0       7.847   1.787   2.067  0.00  0.00           H+0
HETATM   33  H   UNK     0       7.690   2.858   0.649  0.00  0.00           H+0
HETATM   34  H   UNK     0       9.957   0.883   0.374  0.00  0.00           H+0
HETATM   35  H   UNK     0       8.601   1.302  -0.719  0.00  0.00           H+0
HETATM   36  H   UNK     0       8.403  -1.048   0.064  0.00  0.00           H+0
HETATM   37  H   UNK     0       8.179  -0.364   1.764  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.598   0.307  -0.705  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.216   0.919   0.956  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.128  -2.021   0.039  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.995  -1.471   1.768  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.847  -1.993   0.857  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.888  -0.277   1.240  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.235  -1.472  -1.628  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.187   1.230  -0.693  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.899  -0.411  -0.081  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.384  -1.041  -2.997  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.259  -0.538  -1.864  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.732  -1.138   1.070  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.308  -3.613  -0.087  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.486  -2.725  -1.473  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.673  -2.927   0.099  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.177   0.519   2.662  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.983  -1.147   2.488  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.212  -0.939   2.439  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.476  -0.436  -1.056  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.697  -2.287   0.018  0.00  0.00           H+0
HETATM   58  H   UNK     0      -6.046   1.749  -0.050  0.00  0.00           H+0
HETATM   59  H   UNK     0      -8.551   1.198   0.010  0.00  0.00           H+0
HETATM   60  H   UNK     0      -7.570   0.545  -1.412  0.00  0.00           H+0
HETATM   61  H   UNK     0      -8.007  -0.554  -0.080  0.00  0.00           H+0
HETATM   62  H   UNK     0      -7.371  -0.967   2.392  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.114   1.511  -0.579  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.050   2.691   1.154  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.448   1.032   0.656  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.782   2.462  -0.958  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.495   2.950  -0.745  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.078   1.963  -2.169  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   34   35                                             
CONECT    3    2    4   36   37                                             
CONECT    4    3    5   38   39                                             
CONECT    5    4    6   40   41                                             
CONECT    6    5    7   42   43                                             
CONECT    7    6    8    9   44                                             
CONECT    8    7   45                                                       
CONECT    9    7   10   46                                                  
CONECT   10    9   11   47                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   29   48                                             
CONECT   15   14   16   17   49                                             
CONECT   16   15   50   51   52                                             
CONECT   17   15   18                                                       
CONECT   18   17   19   20   27                                             
CONECT   19   18   53   54   55                                             
CONECT   20   18   21   22   56                                             
CONECT   21   20   57                                                       
CONECT   22   20   23   24   58                                             
CONECT   23   22   59   60   61                                             
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   62                                                       
CONECT   27   18   28   29   63                                             
CONECT   28   27   64                                                       
CONECT   29   27   30   14   65                                             
CONECT   30   29   66   67   68                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    2                                                            
CONECT   35    2                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47   10                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   16                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   23                                                            
CONECT   61   23                                                            
CONECT   62   26                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
CONECT   65   29                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   30                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  136    0
END

RDKit          3D

68 68  0  0  0  0  0  0  0  0999 V2000
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    1.7988   -0.8262   -2.1203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445   -0.7437   -2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
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 29 30  1  0
 29 14  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  6 42  1  0
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  7 44  1  6
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 27 63  1  6
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 29 65  1  1
 30 66  1  0
 30 67  1  0
 30 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Botcinerate	Generator
Homobotcinolide	MeSH
(2R,3S)-3-Hydroxy-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoate	Generator

Chemical Formula

C₂₂H₃₈O₈

Average Mass

430.5380 Da

Monoisotopic Mass

430.25667 Da

IUPAC Name

(2R,3S)-3-hydroxy-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(2E,4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid

Traditional Name

(2R,3S)-3-hydroxy-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(2E,4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC[C@H](O)\C=C\C(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](O)[C@@H](C)C(O)=O)[C@@H](O)[C@@H]1C

InChI Identifier

InChI=1S/C22H38O8/c1-6-7-8-9-10-16(23)11-12-17(24)29-18-13(2)19(25)22(5,30-15(18)4)20(26)14(3)21(27)28/h11-16,18-20,23,25-26H,6-10H2,1-5H3,(H,27,28)/b12-11+/t13-,14-,15+,16+,18-,19+,20+,22+/m1/s1

InChI Key

CIZAXJJDWVUEEL-AFQFPRFFSA-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
Botrytis cinerea	NPAtlas	16643065

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	2.5	ALOGPS
logP	2.87	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	110.89 m³·mol⁻¹	ChemAxon
Polarizability	47.29 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA005226

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9886397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11711675

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tani H, Koshino H, Sakuno E, Cutler HG, Nakajima H: Botcinins E and F and Botcinolide from Botrytis cinerea and structural revision of botcinolides. J Nat Prod. 2006 Apr;69(4):722-5. doi: 10.1021/np060071x. [PubMed:16643065 ]
Shiina I, Fukui H: Chemistry and structural determination of botcinolides, botcinins, and botcinic acids. Chem Commun (Camb). 2009 Jan 28;(4):385-400. doi: 10.1039/b814375g. Epub 2008 Dec 3. [PubMed:19137164 ]

Showing NP-Card for Botcineric acid (NP0006330)

MOL for NP0006330 (Botcineric acid)

3D MOL for NP0006330 (Botcineric acid)

3D SDF for NP0006330 (Botcineric acid)

3D-SDF for NP0006330 (Botcineric acid)

PDB for NP0006330 (Botcineric acid)

3D PDB for NP0006330 (Botcineric acid)

SMILES for NP0006330 (Botcineric acid)

INCHI for NP0006330 (Botcineric acid)

Structure for NP0006330 (Botcineric acid)

3D Structure for NP0006330 (Botcineric acid)