NP-MRD: Showing NP-Card for Arisugacin C (NP0003201)

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Record Information

Version

1.0

Created at

2020-12-09 00:31:49 UTC

Updated at

2021-07-15 16:45:47 UTC

NP-MRD ID

NP0003201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arisugacin C

Provided By

NPAtlas

Description

Arisugacin C is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Arisugacin C is found in Penicillium. It was first documented in 2000 (PMID: 10724008). Based on a literature review very few articles have been published on arisugacin C (PMID: 27067533) (PMID: 24482051) (PMID: 24166709).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242117463D          

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    5.7349   -1.6283    0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5929    0.4870   -3.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493   -0.8018   -2.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    2.4237   -0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094    2.0580   -2.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    2.3548   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4492    0.7505   -2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1068    2.1550    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6470   -0.1938   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8357    0.6400   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9896    2.6577    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672    2.4334   -0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1175   -0.8471    3.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487    0.3453    2.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0953   -1.5152    1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -2.0812    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6137   -1.2431   -1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727   -2.4216   -1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3388   -2.0856   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2735   -2.5831    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6713   -2.3118    1.2963 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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 16 31  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33  3  1  0  0  0  0
 13  7  1  0  0  0  0
 29 15  1  0  0  0  0
 31  9  1  0  0  0  0
 29 20  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  4 37  1  0  0  0  0
  5 38  1  0  0  0  0
  8 39  1  0  0  0  0
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 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
 32 64  1  0  0  0  0
 33 65  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C([H])([H])C([H])([H])[C@]3(OC4=C(C(=O)OC(=C4[H])C4=C([H])C([H])=C(OC([H])([H])[H])C([H])=C4[H])C([H])([H])[C@]3([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])C(=O)C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O6/c1-24(2)22(28)10-11-25(3)21-14-18-20(33-26(21,4)12-13-27(24,25)30)15-19(32-23(18)29)16-6-8-17(31-5)9-7-16/h6-9,15,21,30H,10-14H2,1-5H3/t21-,25-,26-,27-/m1/s1

> <INCHI_KEY>
XKDGQMPLQPRTCS-HHPVDLARSA-N

> <FORMULA>
C27H32O6

> <MOLECULAR_WEIGHT>
452.547

> <EXACT_MASS>
452.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.19561566711519

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5aR,7aS,11aR,11bR)-7a-hydroxy-3-(4-methoxyphenyl)-5a,8,8,11a-tetramethyl-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphene-1,9-dione

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
3.748032840666667

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.36276492983811

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.860574501824502

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2971815900431913

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
125.02629999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5aR,7aS,11aR,11bR)-7a-hydroxy-3-(4-methoxyphenyl)-5a,8,8,11a-tetramethyl-6,7,10,11,11b,12-hexahydro-2,5-dioxatetraphene-1,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
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   -0.9291   -2.4729    0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6713   -2.3118    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
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 18 19  1  0
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 22 23  1  6
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 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  6
 16 31  1  0
  6 32  1  0
 32 33  2  0
 33  3  1  0
 13  7  1  0
 29 15  1  0
 31  9  1  0
 29 20  1  0
  1 34  1  0
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  1 36  1  0
  4 37  1  0
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 30 61  1  0
 30 62  1  0
 30 63  1  0
 32 64  1  0
 33 65  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       9.664   1.115   0.647  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.057  -0.131   0.903  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.687  -0.260   0.706  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.896   0.774   0.272  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.521   0.605   0.086  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.915  -0.590   0.328  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.502  -0.811   0.150  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.646   0.157  -0.275  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.286  -0.097  -0.434  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.830  -1.364  -0.146  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.737  -2.306   0.281  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.382  -3.500   0.565  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.986  -2.001   0.406  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.619  -1.743  -0.284  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.359  -0.418  -0.182  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.888   0.451  -1.265  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.631  -0.275  -2.584  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.694   1.660  -1.571  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.189   1.377  -1.480  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.425   0.804  -0.119  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.605   1.569   0.758  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.812   0.964   0.402  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.845   0.090  -0.237  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.234   2.397   0.169  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.742   0.632   1.850  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.579   1.072   2.601  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.672  -0.217   2.361  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.063  -1.147   1.380  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.850  -0.579  -0.012  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.410  -1.568  -0.974  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.421   0.924  -0.877  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.735  -1.628   0.768  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.087  -1.479   0.956  0.00  0.00           C+0
HETATM   34  H   UNK     0      10.769   0.920   0.574  0.00  0.00           H+0
HETATM   35  H   UNK     0       9.321   1.477  -0.358  0.00  0.00           H+0
HETATM   36  H   UNK     0       9.428   1.842   1.454  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.343   1.745   0.068  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.979   1.453  -0.251  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.982   1.145  -0.503  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.929  -2.473   0.463  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.678  -2.160  -1.334  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.001   0.026   0.797  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.395  -0.995  -2.846  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.593   0.487  -3.395  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.349  -0.802  -2.562  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.483   2.424  -0.779  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.409   2.058  -2.564  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.687   2.355  -1.627  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.449   0.751  -2.324  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.107   2.155   1.337  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.647  -0.194  -1.268  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.836   0.640  -0.262  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.072  -0.789   0.436  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.422   3.113   0.118  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.990   2.658   0.956  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.767   2.433  -0.806  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.117  -0.847   3.187  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.849   0.345   2.885  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.095  -1.515   1.834  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.698  -2.081   1.358  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.614  -1.243  -1.980  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.673  -2.422  -1.052  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.339  -2.086  -0.588  0.00  0.00           H+0
HETATM   64  H   UNK     0       5.274  -2.583   0.965  0.00  0.00           H+0
HETATM   65  H   UNK     0       7.671  -2.312   1.296  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5   37                                                  
CONECT    5    4    6   38                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   39                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14   10   15   40   41                                             
CONECT   15   14   16   29   42                                             
CONECT   16   15   17   18   31                                             
CONECT   17   16   43   44   45                                             
CONECT   18   16   19   46   47                                             
CONECT   19   18   20   48   49                                             
CONECT   20   19   21   22   29                                             
CONECT   21   20   50                                                       
CONECT   22   20   23   24   25                                             
CONECT   23   22   51   52   53                                             
CONECT   24   22   54   55   56                                             
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   57   58                                             
CONECT   28   27   29   59   60                                             
CONECT   29   28   30   15   20                                             
CONECT   30   29   61   62   63                                             
CONECT   31   16    9                                                       
CONECT   32    6   33   64                                                  
CONECT   33   32    3   65                                                  
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    8                                                            
CONECT   40   14                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   21                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  138    0
END

RDKit          3D

65 69  0  0  0  0  0  0  0  0999 V2000
    9.6643    1.1150    0.6465 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0568   -0.1312    0.9028 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6874   -0.2597    0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8960    0.7741    0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5210    0.6045    0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -0.5904    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5016   -0.8106    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6461    0.1565   -0.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2858   -0.0966   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8303   -1.3641   -0.1460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -2.3064    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3816   -3.4998    0.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9858   -2.0009    0.4062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6191   -1.7434   -0.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -0.4175   -0.1816 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8884    0.4513   -1.2650 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6309   -0.2745   -2.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6942    1.6599   -1.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1886    1.3771   -1.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4252    0.8040   -0.1192 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6047    1.5686    0.7580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8117    0.9635    0.4017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8454    0.0899   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2345    2.3965    0.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    0.6323    1.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5786    1.0718    2.6012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6716   -0.2170    2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0629   -1.1466    1.3798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -0.5788   -0.0122 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4104   -1.5681   -0.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4206    0.9239   -0.8771 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7349   -1.6283    0.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0871   -1.4792    0.9559 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7690    0.9203    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3206    1.4768   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4277    1.8417    1.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3432    1.7449    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9787    1.4526   -0.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823    1.1451   -0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9291   -2.4729    0.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6782   -2.1598   -1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0014    0.0259    0.7973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3951   -0.9953   -2.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5929    0.4870   -3.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493   -0.8018   -2.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833    2.4237   -0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094    2.0580   -2.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6870    2.3548   -1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4492    0.7505   -2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1068    2.1550    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6470   -0.1938   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8357    0.6400   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0716   -0.7889    0.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    3.1128    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9896    2.6577    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672    2.4334   -0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1175   -0.8471    3.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487    0.3453    2.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0953   -1.5152    1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980   -2.0812    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6137   -1.2431   -1.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727   -2.4216   -1.0517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3388   -2.0856   -0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2735   -2.5831    0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6713   -2.3118    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
 20 22  1  0
 22 23  1  6
 22 24  1  0
 22 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  6
 16 31  1  0
  6 32  1  0
 32 33  2  0
 33  3  1  0
 13  7  1  0
 29 15  1  0
 31  9  1  0
 29 20  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  8 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  1
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 28 60  1  0
 30 61  1  0
 30 62  1  0
 30 63  1  0
 32 64  1  0
 33 65  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₆

Average Mass

452.5470 Da

Monoisotopic Mass

452.21989 Da

IUPAC Name

(5aR,7aS,11aR,11bR)-7a-hydroxy-3-(4-methoxyphenyl)-5a,8,8,11a-tetramethyl-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphene-1,9-dione

Traditional Name

(5aR,7aS,11aR,11bR)-7a-hydroxy-3-(4-methoxyphenyl)-5a,8,8,11a-tetramethyl-6,7,10,11,11b,12-hexahydro-2,5-dioxatetraphene-1,9-dione

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC2=C(C[C@H]3[C@@](C)(CC[C@@]4(O)C(C)(C)C(=O)CC[C@]34C)O2)C(=O)O1

InChI Identifier

InChI=1S/C27H32O6/c1-24(2)22(28)10-11-25(3)21-14-18-20(33-26(21,4)12-13-27(24,25)30)15-19(32-23(18)29)16-6-8-17(31-5)9-7-16/h6-9,15,21,30H,10-14H2,1-5H3/t21-,25-,26-,27-/m1/s1

InChI Key

XKDGQMPLQPRTCS-HHPVDLARSA-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	NPAtlas	10724008

Species Where Detected

Species Name	Source	Reference
Penicillium sp. FO-4259-11	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	4.17	ALOGPS
logP	3.75	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	125.03 m³·mol⁻¹	ChemAxon
Polarizability	50.2 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	No	ChemAxon

External Links

NPAtlas ID

NPA014139

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015475

Chemspider ID

8679213

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

65437

Good Scents ID

Not Available

References

General References

Otoguro K, Shiomi K, Yamaguchi Y, Arai N, Sunazuka T, Masuma R, Iwai Y, Omura S: Arisugacins C and D, novel acetylcholinesterase inhibitors and their related novel metabolites produced by Penicilium sp. FO-4259-11. J Antibiot (Tokyo). 2000 Jan;53(1):50-7. doi: 10.7164/antibiotics.53.50. [PubMed:10724008 ]
Ding B, Wang Z, Huang X, Liu Y, Chen W, She Z: Bioactive alpha-pyrone meroterpenoids from mangrove endophytic fungus Penicillium sp. Nat Prod Res. 2016 Dec;30(24):2805-2812. doi: 10.1080/14786419.2016.1164702. Epub 2016 Apr 11. [PubMed:27067533 ]
Li XD, Miao FP, Liang XR, Ji NY: Meroterpenes from an algicolous strain of Penicillium echinulatum. Magn Reson Chem. 2014 May;52(5):247-50. doi: 10.1002/mrc.4049. Epub 2014 Jan 30. [PubMed:24482051 ]
Sun X, Kong X, Gao H, Zhu T, Wu G, Gu Q, Li D: Two new meroterpenoids produced by the endophytic fungus Penicillium sp. SXH-65. Arch Pharm Res. 2014 Aug;37(8):978-82. doi: 10.1007/s12272-013-0268-2. Epub 2013 Oct 30. [PubMed:24166709 ]

Showing NP-Card for Arisugacin C (NP0003201)

MOL for NP0003201 (Arisugacin C)

3D MOL for NP0003201 (Arisugacin C)

3D SDF for NP0003201 (Arisugacin C)

3D-SDF for NP0003201 (Arisugacin C)

PDB for NP0003201 (Arisugacin C)

3D PDB for NP0003201 (Arisugacin C)

SMILES for NP0003201 (Arisugacin C)

INCHI for NP0003201 (Arisugacin C)

Structure for NP0003201 (Arisugacin C)

3D Structure for NP0003201 (Arisugacin C)