NP-MRD: Showing NP-Card for Xanthoepocin (NP0003547)

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Record Information

Version

2.0

Created at

2020-12-09 00:46:11 UTC

Updated at

2021-07-15 16:46:42 UTC

NP-MRD ID

NP0003547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xanthoepocin

Provided By

NPAtlas

Description

Xanthoepocin is found in Penicillium simplicissimum. Xanthoepocin was first documented in 2000 (PMID: 11099226). Based on a literature review very few articles have been published on 14-{2,15-dihydroxy-12-methoxy-6-methyl-4,11-dioxo-5,13-dioxatetracyclo[8.5.0.0³,⁸.0¹²,¹⁴]Pentadeca-1(10),2,6,8-tetraen-14-yl}-2,15-dihydroxy-12-methoxy-6-methyl-5,13-dioxatetracyclo[8.5.0.0³,⁸.0¹²,¹⁴]Pentadeca-1(10),2,6,8-tetraene-4,11-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 66 73  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117483D          

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 42 66  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)OC(=C([H])C2=C([H])C2=C1[C@@]([H])(O[H])[C@@]1(O[C@]1(OC([H])([H])[H])C2=O)[C@@]12O[C@]1(OC([H])([H])[H])C(=O)C1=C([H])C3=C(C(=O)OC(=C3[H])C([H])([H])[H])C(O[H])=C1[C@@]2([H])O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O14/c1-9-5-11-7-13-17(19(31)15(11)25(37)41-9)23(35)27(29(39-3,43-27)21(13)33)28-24(36)18-14(22(34)30(28,40-4)44-28)8-12-6-10(2)42-26(38)16(12)20(18)32/h5-8,23-24,31-32,35-36H,1-4H3/t23-,24-,27-,28-,29-,30-/m1/s1

> <INCHI_KEY>
KJPAOKCLRDGPMI-UHFFFAOYSA-N

> <FORMULA>
C30H22O14

> <MOLECULAR_WEIGHT>
606.492

> <EXACT_MASS>
606.100955388

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
58.17840863899867

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(12S,14R,15R)-14-[(12S,14R,15R)-2,15-dihydroxy-12-methoxy-6-methyl-4,11-dioxo-5,13-dioxatetracyclo[8.5.0.0^{3,8}.0^{12,14}]pentadeca-1,3(8),6,9-tetraen-14-yl]-2,15-dihydroxy-12-methoxy-6-methyl-5,13-dioxatetracyclo[8.5.0.0^{3,8}.0^{12,14}]pentadeca-1(10),2,6,8-tetraene-4,11-dione

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
3.3003047826666667

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.540892704370782

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.93913248313625

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6561077687294263

> <JCHEM_POLAR_SURFACE_AREA>
211.17999999999995

> <JCHEM_REFRACTIVITY>
146.60899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S,14R,15R)-14-[(12S,14R,15R)-2,15-dihydroxy-12-methoxy-6-methyl-4,11-dioxo-5,13-dioxatetracyclo[8.5.0.0^{3,8}.0^{12,14}]pentadeca-1,3(8),6,9-tetraen-14-yl]-2,15-dihydroxy-12-methoxy-6-methyl-5,13-dioxatetracyclo[8.5.0.0^{3,8}.0^{12,14}]pentadeca-1(10),2,6,8-tetraene-4,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 73  0  0  0  0  0  0  0  0999 V2000
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 38 40  1  0
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 41 42  1  0
 31 43  1  0
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  5  3  1  0
  8  6  1  0
 25 13  1  0
 41 30  1  0
 43  3  1  0
 26  6  1  0
 40 33  1  0
 22 15  2  0
  1 45  1  0
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 29 60  1  0
 32 61  1  0
 34 62  1  0
 36 63  1  0
 36 64  1  0
 36 65  1  0
 42 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      -1.372   2.395   2.537  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.329   1.452   2.595  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.813   0.289   1.950  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.008  -0.804   1.862  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.570  -0.111   0.666  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.601   0.216  -0.235  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.004   0.910  -1.435  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.004   1.473  -0.646  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.726   2.626   0.076  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.884   2.970   0.769  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.312   1.526  -1.338  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.630   2.515  -2.049  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.281   0.439  -1.224  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.626   0.619  -1.454  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.515  -0.439  -1.335  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.867  -0.277  -1.561  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.700  -1.376  -1.425  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.177  -1.280  -1.653  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.233  -2.551  -1.089  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.925  -2.715  -0.869  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.582  -3.882  -0.552  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.033  -1.695  -0.978  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.685  -1.862  -0.752  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.156  -3.073  -0.399  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.813  -0.778  -0.879  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.386  -1.009  -0.628  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.318  -1.945   0.432  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.615  -0.942  -0.032  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.451  -0.930  -1.420  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.011  -0.516   0.218  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.313  -0.057   1.472  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.570   0.353   1.834  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.543   0.283   0.864  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.848   0.675   1.133  0.00  0.00           C+0
HETATM   35  C   UNK     0      -7.829   0.609   0.170  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.212   1.027   0.465  0.00  0.00           C+0
HETATM   37  O   UNK     0      -7.521   0.168  -1.020  0.00  0.00           O+0
HETATM   38  C   UNK     0      -6.282  -0.222  -1.334  0.00  0.00           C+0
HETATM   39  O   UNK     0      -6.100  -0.627  -2.505  0.00  0.00           O+0
HETATM   40  C   UNK     0      -5.261  -0.180  -0.416  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.985  -0.594  -0.780  0.00  0.00           C+0
HETATM   42  O   UNK     0      -3.601  -1.058  -1.985  0.00  0.00           O+0
HETATM   43  C   UNK     0      -2.187  -0.014   2.426  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.480  -0.248   3.640  0.00  0.00           O+0
HETATM   45  H   UNK     0      -1.663   2.637   1.512  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.922   3.338   2.965  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.206   2.133   3.185  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.138   2.111   1.446  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.709   3.301   0.144  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.566   3.785   1.484  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.991   1.609  -1.733  0.00  0.00           H+0
HETATM   52  H   UNK     0       7.259   0.676  -1.835  0.00  0.00           H+0
HETATM   53  H   UNK     0       9.561  -0.268  -1.538  0.00  0.00           H+0
HETATM   54  H   UNK     0       9.461  -1.701  -2.649  0.00  0.00           H+0
HETATM   55  H   UNK     0       9.719  -1.920  -0.905  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.466  -3.966  -0.237  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.975  -1.478  -1.566  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.034  -1.658   1.079  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.567  -2.004   0.358  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.428  -1.874  -1.714  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.747   0.703   2.838  0.00  0.00           H+0
HETATM   62  H   UNK     0      -7.054   1.030   2.123  0.00  0.00           H+0
HETATM   63  H   UNK     0      -9.646   1.655  -0.351  0.00  0.00           H+0
HETATM   64  H   UNK     0      -9.829   0.099   0.514  0.00  0.00           H+0
HETATM   65  H   UNK     0      -9.296   1.623   1.391  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.096  -1.192  -2.799  0.00  0.00           H+0
CONECT    1    2   45   46   47                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5   43                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   28    3                                             
CONECT    6    5    7    8   26                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   11    6                                             
CONECT    9    8   10                                                       
CONECT   10    9   48   49   50                                             
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15   51                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   52                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   53   54   55                                             
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   15                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   56                                                       
CONECT   25   23   26   13                                                  
CONECT   26   25   27    6   57                                             
CONECT   27   26   58                                                       
CONECT   28    5   29   30   59                                             
CONECT   29   28   60                                                       
CONECT   30   28   31   41                                                  
CONECT   31   30   32   43                                                  
CONECT   32   31   33   61                                                  
CONECT   33   32   34   40                                                  
CONECT   34   33   35   62                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   63   64   65                                             
CONECT   37   35   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   33                                                  
CONECT   41   40   42   30                                                  
CONECT   42   41   66                                                       
CONECT   43   31   44    3                                                  
CONECT   44   43                                                            
CONECT   45    1                                                            
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48   10                                                            
CONECT   49   10                                                            
CONECT   50   10                                                            
CONECT   51   14                                                            
CONECT   52   16                                                            
CONECT   53   18                                                            
CONECT   54   18                                                            
CONECT   55   18                                                            
CONECT   56   24                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   32                                                            
CONECT   62   34                                                            
CONECT   63   36                                                            
CONECT   64   36                                                            
CONECT   65   36                                                            
CONECT   66   42                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  146    0
END

RDKit          3D

66 73  0  0  0  0  0  0  0  0999 V2000
   -1.3719    2.3948    2.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    1.4524    2.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3122    1.5259   -1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304    2.5154   -2.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6261    0.6192   -1.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5152   -0.4390   -1.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0962   -1.1924   -2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  6
  7  8  1  0
  8  9  1  1
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 11 12  2  0
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  5 28  1  0
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 35 37  1  0
 37 38  1  0
 38 39  2  0
 38 40  1  0
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 41 42  1  0
 31 43  1  0
 43 44  2  0
  5  3  1  0
  8  6  1  0
 25 13  1  0
 41 30  1  0
 43  3  1  0
 26  6  1  0
 40 33  1  0
 22 15  2  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
 10 48  1  0
 10 49  1  0
 10 50  1  0
 14 51  1  0
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 24 56  1  0
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 32 61  1  0
 34 62  1  0
 36 63  1  0
 36 64  1  0
 36 65  1  0
 42 66  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₄

Average Mass

606.4920 Da

Monoisotopic Mass

606.10096 Da

IUPAC Name

(12S,14R,15R)-14-[(12S,14R,15R)-2,15-dihydroxy-12-methoxy-6-methyl-4,11-dioxo-5,13-dioxatetracyclo[8.5.0.0^{3,8}.0^{12,14}]pentadeca-1,3(8),6,9-tetraen-14-yl]-2,15-dihydroxy-12-methoxy-6-methyl-5,13-dioxatetracyclo[8.5.0.0^{3,8}.0^{12,14}]pentadeca-1(10),2,6,8-tetraene-4,11-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

COC12OC1(C(O)C1=C(C=C3C=C(C)OC(=O)C3=C1O)C2=O)C12OC1(OC)C(=O)C1=C(C2O)C(O)=C2C(=O)OC(C)=CC2=C1

InChI Identifier

InChI=1S/C30H22O14/c1-9-5-11-7-13-17(19(31)15(11)25(37)41-9)23(35)27(29(39-3,43-27)21(13)33)28-24(36)18-14(22(34)30(28,40-4)44-28)8-12-6-10(2)42-26(38)16(12)20(18)32/h5-8,23-24,31-32,35-36H,1-4H3

InChI Key

KJPAOKCLRDGPMI-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
Penicillium simplicissimum	NPAtlas	11099226

Species Where Detected

Species Name	Source	Reference
Penicillium simplicissimum IFO5762	KNApSAcK Database	22123792

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	2.15	ALOGPS
logP	3.3	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	211.18 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	146.61 m³·mol⁻¹	ChemAxon
Polarizability	58.18 Å³	ChemAxon
Number of Rings	8	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

NPA005720

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4587826

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5482316

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Igarashi Y, Kuwamori Y, Takagi K, Ando T, Fudou R, Furumai T, Oki T: Xanthoepocin, a new antibiotic from Penicillium simplicissimum IFO5762. J Antibiot (Tokyo). 2000 Sep;53(9):928-33. doi: 10.7164/antibiotics.53.928. [PubMed:11099226 ]

Showing NP-Card for Xanthoepocin (NP0003547)

MOL for NP0003547 (Xanthoepocin)

3D MOL for NP0003547 (Xanthoepocin)

3D SDF for NP0003547 (Xanthoepocin)

3D-SDF for NP0003547 (Xanthoepocin)

PDB for NP0003547 (Xanthoepocin)

3D PDB for NP0003547 (Xanthoepocin)

SMILES for NP0003547 (Xanthoepocin)

INCHI for NP0003547 (Xanthoepocin)

Structure for NP0003547 (Xanthoepocin)

3D Structure for NP0003547 (Xanthoepocin)