NP-MRD: Showing NP-Card for Helicusin E (NP0011584)

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Record Information

Version

2.0

Created at

2021-01-05 21:13:22 UTC

Updated at

2021-07-15 17:09:21 UTC

NP-MRD ID

NP0011584

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Helicusin E

Provided By

NPAtlas

Description

Helicusin E belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. Helicusin E is found in Bartalinia and Bartalinia robillardoides. Helicusin E was first documented in 2013 (PMID: 23481677). Based on a literature review very few articles have been published on Helicusin E.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242116573D          

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    3.7561   -1.5535    0.3870 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0066   -2.8308    1.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1100    0.2817   -1.4906 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2397    1.4726   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5421   -0.1437   -0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0670   -0.9977   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5748    2.1721    0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1128    1.1716    2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8019   -1.2430    1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7990   -1.6290   -0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2965   -1.3256    0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629    0.0347   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2093    1.5826    2.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1382   -0.7635   -0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3164   -3.6372    0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8678   -2.5986    2.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520   -3.1779    1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5398    0.9593   -2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4975   -0.6619   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7276    0.9242   -2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1294    1.3723    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480    1.0355    2.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  6  0  0  0
  7 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  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
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 19 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 12  1  0  0  0  0
 33 14  1  0  0  0  0
  1 36  1  0  0  0  0
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  1 38  1  0  0  0  0
  2 39  1  0  0  0  0
  2 40  1  0  0  0  0
  3 41  1  6  0  0  0
  4 42  1  0  0  0  0
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  4 44  1  0  0  0  0
  5 45  1  1  0  0  0
  6 46  1  0  0  0  0
  8 47  1  0  0  0  0
  8 48  1  0  0  0  0
  8 49  1  0  0  0  0
  9 50  1  0  0  0  0
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 11 52  1  0  0  0  0
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 24 57  1  0  0  0  0
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 27 61  1  0  0  0  0
 27 62  1  0  0  0  0
 30 63  1  0  0  0  0
 34 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C(=C(/[H])C(=O)O[C@@]1(C(=O)C(Cl)=C2C([H])=C(OC([H])=C2C1=O)C([H])=C([H])[C@@](O[H])(C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H29ClO9/c1-6-14(3)21(30)24(4,33)8-7-15-11-16-17(12-34-15)22(31)25(5,23(32)20(16)26)35-19(29)10-13(2)9-18(27)28/h7-8,10-12,14,21,30,33H,6,9H2,1-5H3,(H,27,28)/b8-7-,13-10+/t14-,21+,24-,25-/m0/s1

> <INCHI_KEY>
KRQJBTNVZHCANM-NVYBTJKXSA-N

> <FORMULA>
C25H29ClO9

> <MOLECULAR_WEIGHT>
508.95

> <EXACT_MASS>
508.1500102

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
52.74914868886047

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-5-{[(7S)-5-chloro-3-[(3S,4R,5S)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.817424774

> <ALOGPS_LOGS>
-5.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.396992633506667

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8546612316532674

> <JCHEM_PKA_STRONGEST_BASIC>
-3.344185483085849

> <JCHEM_POLAR_SURFACE_AREA>
147.43

> <JCHEM_REFRACTIVITY>
130.94559999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-5-{[(7S)-5-chloro-3-[(3S,4R,5S)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 65  0  0  0  0  0  0  0  0999 V2000
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   -2.3307    0.7820    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4383   -1.5835   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9480    1.0355    2.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  2  0
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 25 26  1  0
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 27 28  1  0
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 19 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 35 12  1  0
 33 14  1  0
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  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  6
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  4 43  1  0
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  5 45  1  1
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 26 60  1  0
 27 61  1  0
 27 62  1  0
 30 63  1  0
 34 64  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      -8.935   2.277  -1.385  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.863   2.058  -0.376  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.758   1.096  -0.844  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.447  -0.219  -1.129  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.788   1.055   0.286  0.00  0.00           C+0
HETATM    6  O   UNK     0      -6.330   0.583   1.479  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.458   0.454   0.049  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.361  -1.016   0.244  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.866   0.845  -1.142  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.508   1.043   1.124  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.331   0.782   1.185  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.961   0.479   1.256  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.457  -0.383   0.314  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.929  -0.767   0.280  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.438  -1.583  -0.619  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       0.353  -2.232  -1.837  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       2.837  -1.971  -0.670  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.249  -2.687  -1.665  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.756  -1.554   0.387  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.007  -2.831   1.231  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.056  -1.195  -0.072  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.183  -0.213  -1.037  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.110   0.282  -1.491  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.494   0.222  -1.497  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.597  -0.261  -0.981  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.597  -1.272   0.099  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.905   0.220  -1.489  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.592   0.861  -0.332  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.765   1.275  -0.571  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.027   1.005   0.897  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.211  -0.576   1.296  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.939   0.038   2.164  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.819  -0.207   1.307  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.316   0.616   2.203  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.015   0.932   2.161  0.00  0.00           O+0
HETATM   36  H   UNK     0      -9.034   3.383  -1.554  0.00  0.00           H+0
HETATM   37  H   UNK     0      -9.926   1.930  -0.974  0.00  0.00           H+0
HETATM   38  H   UNK     0      -8.794   1.757  -2.344  0.00  0.00           H+0
HETATM   39  H   UNK     0      -8.247   1.586   0.560  0.00  0.00           H+0
HETATM   40  H   UNK     0      -7.346   2.998  -0.065  0.00  0.00           H+0
HETATM   41  H   UNK     0      -6.240   1.473  -1.736  0.00  0.00           H+0
HETATM   42  H   UNK     0      -8.542  -0.144  -0.952  0.00  0.00           H+0
HETATM   43  H   UNK     0      -7.337  -0.511  -2.209  0.00  0.00           H+0
HETATM   44  H   UNK     0      -7.067  -0.998  -0.455  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.575   2.172   0.499  0.00  0.00           H+0
HETATM   46  H   UNK     0      -6.113   1.172   2.234  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.802  -1.243   1.253  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.799  -1.629  -0.566  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.297  -1.326   0.307  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.463   0.035  -1.550  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.085   1.713   1.798  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.209   1.583   2.365  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.138  -0.764  -0.429  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.316  -3.637   0.948  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.868  -2.599   2.309  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.052  -3.178   1.090  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.540   0.959  -2.275  0.00  0.00           H+0
HETATM   58  H   UNK     0       7.047  -0.892   1.018  0.00  0.00           H+0
HETATM   59  H   UNK     0       8.638  -1.438   0.497  0.00  0.00           H+0
HETATM   60  H   UNK     0       7.148  -2.228  -0.155  0.00  0.00           H+0
HETATM   61  H   UNK     0       9.498  -0.662  -1.857  0.00  0.00           H+0
HETATM   62  H   UNK     0       8.728   0.924  -2.313  0.00  0.00           H+0
HETATM   63  H   UNK     0       8.129   1.372   1.105  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.948   1.036   2.956  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3   39   40                                             
CONECT    3    2    4    5   41                                             
CONECT    4    3   42   43   44                                             
CONECT    5    3    6    7   45                                             
CONECT    6    5   46                                                       
CONECT    7    5    8    9   10                                             
CONECT    8    7   47   48   49                                             
CONECT    9    7   50                                                       
CONECT   10    7   11   51                                                  
CONECT   11   10   12   52                                                  
CONECT   12   11   13   35                                                  
CONECT   13   12   14   53                                                  
CONECT   14   13   15   33                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   31                                             
CONECT   20   19   54   55   56                                             
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   57                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   58   59   60                                             
CONECT   27   25   28   61   62                                             
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   63                                                       
CONECT   31   19   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   14                                                  
CONECT   34   33   35   64                                                  
CONECT   35   34   12                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    2                                                            
CONECT   40    2                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    4                                                            
CONECT   45    5                                                            
CONECT   46    6                                                            
CONECT   47    8                                                            
CONECT   48    8                                                            
CONECT   49    8                                                            
CONECT   50    9                                                            
CONECT   51   10                                                            
CONECT   52   11                                                            
CONECT   53   13                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   20                                                            
CONECT   57   24                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   30                                                            
CONECT   64   34                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  130    0
END

RDKit          3D

64 65  0  0  0  0  0  0  0  0999 V2000
   -8.9350    2.2769   -1.3845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8633    2.0582   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7579    1.0962   -0.8440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4475   -0.2193   -1.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7878    1.0549    0.2863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3299    0.5830    1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4583    0.4542    0.0488 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3606   -1.0162    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8662    0.8447   -1.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5077    1.0428    1.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3307    0.7820    1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9614    0.4786    1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4574   -0.3827    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -0.7672    0.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383   -1.5835   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3533   -2.2320   -1.8374 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    4.0066   -2.8308    1.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0565   -1.1950   -0.0718 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1830   -0.2127   -1.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4943    0.2218   -1.4970 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5968   -0.2606   -0.9811 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5974   -1.2721    0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9048    0.2203   -1.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5917    0.8605   -0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7653    1.2749   -0.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0266    1.0053    0.8965 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2108   -0.5755    1.2960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9394    0.0381    2.1645 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.2068    1.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3162    0.6159    2.2029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0153    0.9319    2.1611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0343    3.3831   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9262    1.9297   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7941    1.7573   -2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2474    1.5863    0.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3458    2.9979   -0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2397    1.4726   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5421   -0.1437   -0.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3365   -0.5112   -2.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0670   -0.9977   -0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5748    2.1721    0.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1128    1.1716    2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8019   -1.2430    1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7990   -1.6290   -0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2965   -1.3256    0.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629    0.0347   -1.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0855    1.7126    1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093    1.5826    2.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1382   -0.7635   -0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3164   -3.6372    0.9483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8678   -2.5986    2.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0520   -3.1779    1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5398    0.9593   -2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0472   -0.8917    1.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6381   -1.4380    0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1476   -2.2284   -0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4975   -0.6619   -1.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7276    0.9242   -2.3129 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1294    1.3723    1.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480    1.0355    2.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  6
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 19 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  2  0
 34 35  1  0
 35 12  1  0
 33 14  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  6
  4 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  1
  6 46  1  0
  8 47  1  0
  8 48  1  0
  8 49  1  0
  9 50  1  0
 10 51  1  0
 11 52  1  0
 13 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 24 57  1  0
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 27 61  1  0
 27 62  1  0
 30 63  1  0
 34 64  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3E)-5-{[(7S)-5-chloro-3-(3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoate	Generator

Chemical Formula

C₂₅H₂₉ClO₉

Average Mass

508.9500 Da

Monoisotopic Mass

508.15001 Da

IUPAC Name

(3E)-5-{[(7S)-5-chloro-3-[(3S,4R,5S)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

Traditional Name

(3E)-5-{[(7S)-5-chloro-3-[(3S,4R,5S)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-methyl-6,8-dioxoisochromen-7-yl]oxy}-3-methyl-5-oxopent-3-enoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C(O)C(C)(O)C=CC1=CC2=C(Cl)C(=O)[C@@](C)(OC(=O)\C=C(/C)CC(O)=O)C(=O)C2=CO1

InChI Identifier

InChI=1S/C25H29ClO9/c1-6-14(3)21(30)24(4,33)8-7-15-11-16-17(12-34-15)22(31)25(5,23(32)20(16)26)35-19(29)10-13(2)9-18(27)28/h7-8,10-12,14,21,30,33H,6,9H2,1-5H3,(H,27,28)/b8-7?,13-10+/t14?,21?,24?,25-/m0/s1

InChI Key

KRQJBTNVZHCANM-NVYBTJKXSA-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
Bartalinia	NPAtlas	23481677
Bartalinia robillardoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
Cyclohexenone
Alpha-acyloxy ketone
Methyl-branched fatty acid
Hydroxy fatty acid
Heterocyclic fatty acid
Halogenated fatty acid
Fatty acid ester
Branched fatty acid
Fatty acyl
Unsaturated fatty acid
Pyran
Dicarboxylic acid or derivatives
Alpha-haloketone
Alpha-chloroketone
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
1,2-diol
Oxacycle
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.03	ALOGPS
logP	2.82	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.95 m³·mol⁻¹	ChemAxon
Polarizability	52.75 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA011532

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jansen N, Ohlendorf B, Erhard A, Bruhn T, Bringmann G, Imhoff JF: Helicusin E, isochromophilone X and isochromophilone XI: new chloroazaphilones produced by the fungus Bartalinia robillardoides strain LF550. Mar Drugs. 2013 Mar 12;11(3):800-16. doi: 10.3390/md11030800. [PubMed:23481677 ]

Showing NP-Card for Helicusin E (NP0011584)

MOL for NP0011584 (Helicusin E)

3D MOL for NP0011584 (Helicusin E)

3D SDF for NP0011584 (Helicusin E)

3D-SDF for NP0011584 (Helicusin E)

PDB for NP0011584 (Helicusin E)

3D PDB for NP0011584 (Helicusin E)

SMILES for NP0011584 (Helicusin E)

INCHI for NP0011584 (Helicusin E)

Structure for NP0011584 (Helicusin E)

3D Structure for NP0011584 (Helicusin E)