NP-MRD: Showing NP-Card for Fellutanine B (NP0003310)

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Record Information

Version

1.0

Created at

2020-12-09 00:32:59 UTC

Updated at

2021-07-15 16:46:05 UTC

NP-MRD ID

NP0003310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fellutanine B

Provided By

NPAtlas

Description

(3R,6S)-3-[(1H-indol-3-yl)methyl]-6-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-3,6-dihydropyrazine-2,5-diol belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Fellutanine B is found in Penicillium fellutanum. It was first documented in 2000 (PMID: 10843594). Based on a literature review very few articles have been published on (3R,6S)-3-[(1H-indol-3-yl)methyl]-6-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-3,6-dihydropyrazine-2,5-diol (PMID: 34380192) (PMID: 34380191) (PMID: 34380190) (PMID: 34380189).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 61 65  0  0  0  0            999 V2000
   -3.6537    0.3645    2.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813   -0.5624    2.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137   -1.2248    1.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3709   -1.8034    0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6482   -2.4567    1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -0.3824    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3160   -0.7576   -0.5712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6037    0.2191   -1.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6337    1.5039   -3.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6428    0.8422   -1.2103 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.5312   -1.9596    0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0702   -0.8755    3.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  3  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
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 31 61  1  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
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   -2.7813   -0.5624    2.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242117463D          

 61 65  0  0  0  0            999 V2000
   -3.6537    0.3645    2.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813   -0.5624    2.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0998    3.6931    0.2185 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5379   -1.1744    1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3582    1.6624   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5775   -1.8624   -2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5338   -1.8724    3.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8066    0.5335    2.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5235    3.2486   -0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
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 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 14  6  2  0  0  0  0
 32 16  1  0  0  0  0
 13  8  1  0  0  0  0
 30 22  1  0  0  0  0
 30 25  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  2 36  1  0  0  0  0
  4 37  1  0  0  0  0
  4 38  1  0  0  0  0
  4 39  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
  5 42  1  0  0  0  0
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 11 46  1  0  0  0  0
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 15 48  1  0  0  0  0
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 16 50  1  6  0  0  0
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 27 58  1  0  0  0  0
 28 59  1  0  0  0  0
 29 60  1  0  0  0  0
 31 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C([H])C(C1=C(C2=C([H])C([H])=C([H])C([H])=C2N1[H])C([H])([H])[C@]1([H])N([H])C(=O)[C@]([H])(N([H])C1=O)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12)(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H28N4O2/c1-4-27(2,3)24-19(18-10-6-8-12-21(18)29-24)14-23-26(33)30-22(25(32)31-23)13-16-15-28-20-11-7-5-9-17(16)20/h4-12,15,22-23,28-29H,1,13-14H2,2-3H3,(H,30,33)(H,31,32)/t22-,23+/m1/s1

> <INCHI_KEY>
PFYKDKMYQRWRGF-PKTZIBPZSA-N

> <FORMULA>
C27H28N4O2

> <MOLECULAR_WEIGHT>
440.547

> <EXACT_MASS>
440.221226158

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.04795320895702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,6S)-3-[(1H-indol-3-yl)methyl]-6-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}piperazine-2,5-dione

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
4.042776799666665

> <ALOGPS_LOGS>
-5.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.356274764709262

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.260419773869943

> <JCHEM_PKA_STRONGEST_BASIC>
-4.454219996365405

> <JCHEM_POLAR_SURFACE_AREA>
89.78

> <JCHEM_REFRACTIVITY>
129.1943

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6S)-3-(1H-indol-3-ylmethyl)-6-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}piperazine-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
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    2.5235    3.2486   -0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
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 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 20 31  1  0
 31 32  1  0
 32 33  2  0
 14  6  2  0
 32 16  1  0
 13  8  1  0
 30 22  1  0
 30 25  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  5 42  1  0
  7 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  6
 17 51  1  0
 20 52  1  1
 21 53  1  0
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 23 55  1  0
 24 56  1  0
 26 57  1  0
 27 58  1  0
 28 59  1  0
 29 60  1  0
 31 61  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      -3.654   0.365   2.861  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.781  -0.562   2.577  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.714  -1.225   1.239  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.371  -1.803   0.970  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.648  -2.457   1.431  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.218  -0.382   0.165  0.00  0.00           C+0
HETATM    7  N   UNK     0      -4.316  -0.758  -0.571  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.604   0.219  -1.448  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.587   0.371  -2.417  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.634   1.504  -3.180  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.734   2.554  -3.050  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.759   2.388  -2.080  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.707   1.250  -1.310  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.836   0.844  -0.280  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.693   1.650   0.117  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.453   1.564  -0.716  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.174   0.308  -0.861  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.462   0.040  -0.371  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.802  -1.137  -0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.459   1.125  -0.274  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.643   0.842  -1.210  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.289  -0.458  -0.810  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.179  -1.692  -1.407  0.00  0.00           C+0
HETATM   24  N   UNK     0       4.928  -2.583  -0.707  0.00  0.00           N+0
HETATM   25  C   UNK     0       5.531  -1.960   0.342  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.378  -2.389   1.340  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.857  -1.527   2.302  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.474  -0.205   2.258  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.627   0.204   1.254  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.131  -0.644   0.273  0.00  0.00           C+0
HETATM   31  N   UNK     0       1.921   2.436  -0.475  0.00  0.00           N+0
HETATM   32  C   UNK     0       0.525   2.630  -0.294  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.100   3.693   0.219  0.00  0.00           O+0
HETATM   34  H   UNK     0      -4.357   0.676   2.116  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.681   0.828   3.835  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.070  -0.876   3.333  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.252  -2.156  -0.053  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.288  -2.756   1.599  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.538  -1.174   1.357  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.358  -2.970   2.371  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.676  -2.039   1.470  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.542  -3.167   0.610  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.876  -1.634  -0.512  0.00  0.00           H+0
HETATM   44  H   UNK     0      -6.301  -0.427  -2.543  0.00  0.00           H+0
HETATM   45  H   UNK     0      -6.420   1.607  -3.943  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.832   3.405  -3.679  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.032   3.171  -1.934  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.013   2.740   0.053  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.351   1.437   1.166  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.813   1.839  -1.777  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.339  -0.451  -1.365  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.902   1.065   0.764  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.358   1.662  -1.195  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.255   0.728  -2.230  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.578  -1.862  -2.291  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.044  -3.587  -0.909  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.683  -3.418   1.384  0.00  0.00           H+0
HETATM   58  H   UNK     0       7.534  -1.872   3.099  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.807   0.534   2.975  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.282   1.248   1.160  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.523   3.249  -0.750  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3   37   38   39                                             
CONECT    5    3   40   41   42                                             
CONECT    6    3    7   14                                                  
CONECT    7    6    8   43                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   44                                                  
CONECT   10    9   11   45                                                  
CONECT   11   10   12   46                                                  
CONECT   12   11   13   47                                                  
CONECT   13   12   14    8                                                  
CONECT   14   13   15    6                                                  
CONECT   15   14   16   48   49                                             
CONECT   16   15   17   32   50                                             
CONECT   17   16   18   51                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   31   52                                             
CONECT   21   20   22   53   54                                             
CONECT   22   21   23   30                                                  
CONECT   23   22   24   55                                                  
CONECT   24   23   25   56                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27   57                                                  
CONECT   27   26   28   58                                                  
CONECT   28   27   29   59                                                  
CONECT   29   28   30   60                                                  
CONECT   30   29   22   25                                                  
CONECT   31   20   32   61                                                  
CONECT   32   31   33   16                                                  
CONECT   33   32                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    2                                                            
CONECT   37    4                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    5                                                            
CONECT   43    7                                                            
CONECT   44    9                                                            
CONECT   45   10                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   20                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
CONECT   57   26                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   31                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  130    0
END

RDKit          3D

61 65  0  0  0  0  0  0  0  0999 V2000
   -3.6537    0.3645    2.8614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7813   -0.5624    2.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137   -1.2248    1.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3709   -1.8034    0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6482   -2.4567    1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -0.3824    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3160   -0.7576   -0.5712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6037    0.2191   -1.4485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5866    0.3707   -2.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6337    1.5039   -3.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7337    2.5537   -3.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7591    2.3875   -2.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7069    1.2497   -1.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    0.8437   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6934    1.6503    0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4529    1.5636   -0.7159 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1737    0.3084   -0.8612 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4624    0.0399   -0.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8022   -1.1375   -0.0002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4595    1.1249   -0.2741 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6428    0.8422   -1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887   -0.4583   -0.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1789   -1.6920   -1.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9277   -2.5835   -0.7071 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5312   -1.9596    0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782   -2.3887    1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8574   -1.5268    2.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4741   -0.2054    2.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6274    0.2043    1.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1315   -0.6435    0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9213    2.4359   -0.4754 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5248    2.6301   -0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0998    3.6931    0.2185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3574    0.6755    2.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.8276    3.8353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0702   -0.8755    3.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2524   -2.1561   -0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877   -2.7555    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379   -1.1744    1.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576   -2.9701    2.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6764   -2.0388    1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417   -3.1670    0.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8757   -1.6339   -0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3005   -0.4266   -2.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4200    1.6068   -3.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8323    3.4047   -3.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0316    3.1709   -1.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0130    2.7397    0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3513    1.4368    1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134    1.8391   -1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3394   -0.4509   -1.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016    1.0646    0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582    1.6624   -1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2550    0.7283   -2.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5775   -1.8624   -2.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0444   -3.5872   -0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6825   -3.4182    1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5338   -1.8724    3.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8066    0.5335    2.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819    1.2475    1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5235    3.2486   -0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 20 31  1  0
 31 32  1  0
 32 33  2  0
 14  6  2  0
 32 16  1  0
 13  8  1  0
 30 22  1  0
 30 25  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  5 42  1  0
  7 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  6
 17 51  1  0
 20 52  1  1
 21 53  1  0
 21 54  1  0
 23 55  1  0
 24 56  1  0
 26 57  1  0
 27 58  1  0
 28 59  1  0
 29 60  1  0
 31 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈N₄O₂

Average Mass

440.5470 Da

Monoisotopic Mass

440.22123 Da

IUPAC Name

(3R,6S)-3-[(1H-indol-3-yl)methyl]-6-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}piperazine-2,5-dione

Traditional Name

(3R,6S)-3-(1H-indol-3-ylmethyl)-6-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}piperazine-2,5-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C1=C(C[C@@H]2NC(=O)[C@@H](CC3=CNC4=CC=CC=C34)NC2=O)C2=CC=CC=C2N1

InChI Identifier

InChI=1S/C27H28N4O2/c1-4-27(2,3)24-19(18-10-6-8-12-21(18)29-24)14-23-26(33)30-22(25(32)31-23)13-16-15-28-20-11-7-5-9-17(16)20/h4-12,15,22-23,28-29H,1,13-14H2,2-3H3,(H,30,33)(H,31,32)/t22-,23+/m1/s1

InChI Key

PFYKDKMYQRWRGF-PKTZIBPZSA-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 fellutanum	NPAtlas	10843594

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Dioxopiperazine
2,5-dioxopiperazine
1,4-diazinane
Piperazine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Lactam
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.05	ALOGPS
logP	4.04	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	11.26	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.78 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.19 m³·mol⁻¹	ChemAxon
Polarizability	49.05 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA016249

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8822129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10646771

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kozlovsky AG, Vinokurova NG, Adanin VM, Burkhardt G, Dahse HM, Grafe U: New diketopiperazine alkaloids from Penicillium fellutanum. J Nat Prod. 2000 May;63(5):698-700. doi: 10.1021/np9903853. [PubMed:10843594 ]
Kim S, Park KY, Chung J, Kim YB, Lee JW, Huh SK: Comparative Analysis of Feasibility of the Retrograde Suction Decompression Technique for Microsurgical Treatment of Large and Giant Internal Carotid Artery Aneurysms. J Korean Neurosurg Soc. 2021 Aug 12. pii: jkns.2021.0066. doi: 10.3340/jkns.2021.0066. [PubMed:34380192 ]
Bahloul M, Kharrat S, Chtara K, Hafdhi M, Turki O, Baccouche N, Ammar R, Kallel N, Hsairi M, Chakroun-Walha O, Hamida CB, Chelly H, Mahfoudh KB, Karoui A, Karray H, Rekik N, Bouaziz M: Clinical characteristics and outcomes of critically ill COVID-19 patients in Sfax, Tunisia. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00129. doi: 10.4266/acc.2021.00129. [PubMed:34380191 ]
Yi J, Kim KH: Identification and infection control of carbapenem-resistant Enterobacterales in intensive care units. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00409. doi: 10.4266/acc.2021.00409. [PubMed:34380190 ]
Lee Y, Kim SH, Hwang HY, Sohn SH, Choi JW, Kim KH: Perfusion parameters during cardiopulmonary bypass as a predictor of acute kidney injury after aortic valve replacement. Acute Crit Care. 2021 Aug 12. pii: acc.2021.00094. doi: 10.4266/acc.2021.00094. [PubMed:34380189 ]

Showing NP-Card for Fellutanine B (NP0003310)

MOL for NP0003310 (Fellutanine B)

3D MOL for NP0003310 (Fellutanine B)

3D SDF for NP0003310 (Fellutanine B)

3D-SDF for NP0003310 (Fellutanine B)

PDB for NP0003310 (Fellutanine B)

3D PDB for NP0003310 (Fellutanine B)

SMILES for NP0003310 (Fellutanine B)

INCHI for NP0003310 (Fellutanine B)

Structure for NP0003310 (Fellutanine B)

3D Structure for NP0003310 (Fellutanine B)