NP-MRD: Showing NP-Card for Apicularen A (NP0001562)

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Record Information

Version

2.0

Created at

2020-09-22 23:34:08 UTC

Updated at

2021-08-10 02:55:15 UTC

NP-MRD ID

NP0001562

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apicularen A

Provided By

NPAtlas

Description

(2Z,4Z)-N-[(1E)-3-{7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.0³,⁸]Heptadeca-3(8),4,6-trien-11-yl}prop-1-en-1-yl]hepta-2,4-dienimidic acid belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. Apicularen A is found in Chomdsomyces robustus, Chondromyces robustus and Chondromyces sp.. Apicularen A was first documented in 1998 (PMID: 10048565). Based on a literature review very few articles have been published on (2Z,4Z)-N-[(1E)-3-{7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.0³,⁸]Heptadeca-3(8),4,6-trien-11-yl}prop-1-en-1-yl]hepta-2,4-dienimidic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117433D          

 63 65  0  0  0  0            999 V2000
   10.3019   -1.2173   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6515   -0.1039   -0.1189 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5606   -0.6403    0.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2821   -0.3062    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8564    0.7037   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184    1.0994   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117433D          

 63 65  0  0  0  0            999 V2000
   10.3019   -1.2173   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6515   -0.1039   -0.1189 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.8564    0.7037   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184    1.0994   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5013    0.6164    0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0674    0.8382    1.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791    0.0590   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  4  5  1  0  0  0  0
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  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  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  1  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
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 17 18  1  0  0  0  0
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 21 22  1  0  0  0  0
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 23 24  1  0  0  0  0
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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
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 29 30  2  0  0  0  0
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 31 13  1  0  0  0  0
 32 15  1  0  0  0  0
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  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
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 27 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001562

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=C([H])C([H])=C1[H])C([H])([H])[C@@]1([H])O[C@@]([H])(C([H])([H])[C@@]([H])(O[H])C1([H])[H])C([H])([H])[C@]([H])(OC2=O)C([H])([H])C(\[H])=C(/[H])N([H])C(=O)C(\[H])=C(\[H])/C(/[H])=C(/[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO6/c1-2-3-4-5-11-23(29)26-12-7-9-19-16-21-15-18(27)14-20(31-21)13-17-8-6-10-22(28)24(17)25(30)32-19/h3-8,10-12,18-21,27-28H,2,9,13-16H2,1H3,(H,26,29)/b4-3-,11-5-,12-7+/t18-,19+,20+,21-/m0/s1

> <INCHI_KEY>
MVOORUCGKRDJFW-UYSGNFFCSA-N

> <FORMULA>
C25H31NO6

> <MOLECULAR_WEIGHT>
441.524

> <EXACT_MASS>
441.215137722

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.784166708782585

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4Z)-N-[(1E)-3-[(1R,11R,13S,15S)-7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.0^{3,8}]heptadeca-3,5,7-trien-11-yl]prop-1-en-1-yl]hepta-2,4-dienamide

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.399267587333333

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.210922373514922

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.782321935668408

> <JCHEM_PKA_STRONGEST_BASIC>
-2.264649197807621

> <JCHEM_POLAR_SURFACE_AREA>
105.09

> <JCHEM_REFRACTIVITY>
124.25509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4Z)-N-[(1E)-3-[(1R,11R,13S,15S)-7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.0^{3,8}]heptadeca-3,5,7-trien-11-yl]prop-1-en-1-yl]hepta-2,4-dienamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
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  4  5  1  0
  5  6  2  0
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 31 13  1  0
 32 15  1  0
 28 22  1  0
  1 33  1  0
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  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
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  5 40  1  0
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 20 57  1  6
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 23 60  1  0
 24 61  1  0
 25 62  1  0
 27 63  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      10.302  -1.217  -0.929  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.652  -0.104  -0.119  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.561  -0.640   0.695  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.282  -0.306   0.654  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.856   0.704  -0.289  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.618   1.099  -0.402  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.501   0.616   0.364  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.586  -0.251   1.241  0.00  0.00           O+0
HETATM    9  N   UNK     0       3.210   1.152   0.119  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.069   0.712   0.846  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.040   0.167   0.225  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.121  -0.278   0.992  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.366   0.461   0.537  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.510  -0.083   1.404  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.711   0.747   1.156  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.225   1.526   2.354  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.395   2.342   1.787  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.220   3.689   2.060  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.498   2.201   0.272  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.451   0.794  -0.208  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.646   0.569  -1.465  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.374  -0.893  -1.556  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.497  -1.704  -1.566  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.427  -3.072  -1.653  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.202  -3.668  -1.733  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.060  -2.869  -1.724  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.868  -3.555  -1.808  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.125  -1.467  -1.635  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.866  -0.706  -1.637  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.035  -1.121  -2.534  0.00  0.00           O+0
HETATM   31  O   UNK     0      -1.551   0.332  -0.810  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.821  -0.035   0.756  0.00  0.00           O+0
HETATM   33  H   UNK     0       9.873  -1.224  -1.936  0.00  0.00           H+0
HETATM   34  H   UNK     0      10.156  -2.156  -0.364  0.00  0.00           H+0
HETATM   35  H   UNK     0      11.401  -1.021  -0.930  0.00  0.00           H+0
HETATM   36  H   UNK     0       9.438   0.702  -0.800  0.00  0.00           H+0
HETATM   37  H   UNK     0      10.415   0.295   0.614  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.845  -1.413   1.425  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.599  -0.819   1.346  0.00  0.00           H+0
HETATM   40  H   UNK     0       7.590   1.166  -0.944  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.456   1.887  -1.178  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.106   1.882  -0.611  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.067   0.838   1.927  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.079   0.059  -0.847  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.040  -0.044   2.064  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.265  -1.379   0.941  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.229   1.506   0.894  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.222  -0.120   2.460  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.673  -1.137   1.084  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.469   1.542   0.411  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.435   2.250   2.643  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.567   0.881   3.164  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.330   1.929   2.206  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.901   4.185   1.548  0.00  0.00           H+0
HETATM   55  H   UNK     0      -6.512   2.655   0.041  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.803   2.903  -0.262  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.484   0.448  -0.399  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.708   1.100  -1.534  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.285   0.915  -2.313  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.482  -1.281  -1.505  0.00  0.00           H+0
HETATM   61  H   UNK     0      -6.325  -3.701  -1.659  0.00  0.00           H+0
HETATM   62  H   UNK     0      -4.139  -4.744  -1.801  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.944  -3.248  -1.812  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3   36   37                                             
CONECT    3    2    4   38                                                  
CONECT    4    3    5   39                                                  
CONECT    5    4    6   40                                                  
CONECT    6    5    7   41                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   42                                                  
CONECT   10    9   11   43                                                  
CONECT   11   10   12   44                                                  
CONECT   12   11   13   45   46                                             
CONECT   13   12   14   31   47                                             
CONECT   14   13   15   48   49                                             
CONECT   15   14   16   32   50                                             
CONECT   16   15   17   51   52                                             
CONECT   17   16   18   19   53                                             
CONECT   18   17   54                                                       
CONECT   19   17   20   55   56                                             
CONECT   20   19   21   32   57                                             
CONECT   21   20   22   58   59                                             
CONECT   22   21   23   28                                                  
CONECT   23   22   24   60                                                  
CONECT   24   23   25   61                                                  
CONECT   25   24   26   62                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   63                                                       
CONECT   28   26   29   22                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   13                                                       
CONECT   32   20   15                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    2                                                            
CONECT   37    2                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    6                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   16                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   19                                                            
CONECT   57   20                                                            
CONECT   58   21                                                            
CONECT   59   21                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   25                                                            
CONECT   63   27                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  130    0
END

RDKit          3D

63 65  0  0  0  0  0  0  0  0999 V2000
   10.3019   -1.2173   -0.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6515   -0.1039   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5606   -0.6403    0.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2821   -0.3062    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8564    0.7037   -0.2886 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6184    1.0994   -0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5013    0.6164    0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5864   -0.2512    1.2408 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2100    1.1520    0.1188 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691    0.7124    0.8457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405    0.1668    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209   -0.2775    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3659    0.4607    0.5368 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5104   -0.0827    1.4042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7107    0.7467    1.1557 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2252    1.5261    2.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3953    2.3424    1.7872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2195    3.6890    2.0603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979    2.2010    0.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4509    0.7939   -0.2080 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6461    0.5687   -1.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741   -0.8929   -1.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4965   -1.7036   -1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4266   -3.0719   -1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2019   -3.6676   -1.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0603   -2.8694   -1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8684   -3.5549   -1.8080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1253   -1.4674   -1.6351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -0.7064   -1.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0350   -1.1212   -2.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5505    0.3316   -0.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8212   -0.0345    0.7557 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8728   -1.2238   -1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1565   -2.1558   -0.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4009   -1.0209   -0.9300 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4375    0.7021   -0.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4145    0.2954    0.6138 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8448   -1.4126    1.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5990   -0.8186    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5902    1.1662   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4563    1.8872   -1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    1.8821   -0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0674    0.8382    1.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791    0.0590   -0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396   -0.0440    2.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2647   -1.3793    0.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2292    1.5060    0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2219   -0.1197    2.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6732   -1.1371    1.0844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4693    1.5420    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4354    2.2502    2.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5675    0.8805    3.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3300    1.9290    2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9012    4.1847    1.5481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5118    2.6549    0.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8035    2.9032   -0.2616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4845    0.4483   -0.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7075    1.1003   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2845    0.9148   -2.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4824   -1.2807   -1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3248   -3.7015   -1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391   -4.7442   -1.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9438   -3.2476   -1.8124 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 20 32  1  0
 31 13  1  0
 32 15  1  0
 28 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  2 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  0
  6 41  1  0
  9 42  1  0
 10 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  6
 14 48  1  0
 14 49  1  0
 15 50  1  6
 16 51  1  0
 16 52  1  0
 17 53  1  1
 18 54  1  0
 19 55  1  0
 19 56  1  0
 20 57  1  6
 21 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 25 62  1  0
 27 63  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2Z,4Z)-N-[(1E)-3-{7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.0,]heptadeca-3(8),4,6-trien-11-yl}prop-1-en-1-yl]hepta-2,4-dienimidate	Generator

Chemical Formula

C₂₅H₃₁NO₆

Average Mass

441.5240 Da

Monoisotopic Mass

441.21514 Da

IUPAC Name

(2Z,4Z)-N-[(1E)-3-[(1R,11R,13S,15S)-7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.0^{3,8}]heptadeca-3,5,7-trien-11-yl]prop-1-en-1-yl]hepta-2,4-dienamide

Traditional Name

(2Z,4Z)-N-[(1E)-3-[(1R,11R,13S,15S)-7,15-dihydroxy-9-oxo-10,17-dioxatricyclo[11.3.1.0^{3,8}]heptadeca-3,5,7-trien-11-yl]prop-1-en-1-yl]hepta-2,4-dienamide

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=C([H])C([H])=C1[H])C([H])([H])[C@@]1([H])O[C@@]([H])(C([H])([H])[C@@]([H])(O[H])C1([H])[H])C([H])([H])[C@]([H])(OC2=O)C([H])([H])C(\[H])=C(/[H])N([H])C(=O)C(\[H])=C(\[H])/C(/[H])=C(/[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H31NO6/c1-2-3-4-5-11-23(29)26-12-7-9-19-16-21-15-18(27)14-20(31-21)13-17-8-6-10-22(28)24(17)25(30)32-19/h3-8,10-12,18-21,27-28H,2,9,13-16H2,1H3,(H,26,29)/b4-3-,11-5-,12-7+/t18-,19+,20+,21-/m0/s1

InChI Key

MVOORUCGKRDJFW-UYSGNFFCSA-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
Chomdsomyces robustus	-	KNApSAcK
Chondromyces robustus	NPAtlas	10048565
Chondromyces sp.	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
N-acyl-amine
Oxane
Vinylogous acid
Carboxamide group
Carboxylic acid ester
Lactone
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
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	3.15	ALOGPS
logP	3.4	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.26 m³·mol⁻¹	ChemAxon
Polarizability	48.78 Å³	ChemAxon
Number of Rings	3	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

NPA002699

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8021854

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9846140

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kunze B, Jansen R, Sasse F, Hofle G, Reichenbach H: Apicularens A and B, new cytostatic macrolides from Chondromyces species (myxobacteria): production, physico-chemical and biological properties. J Antibiot (Tokyo). 1998 Dec;51(12):1075-80. doi: 10.7164/antibiotics.51.1075. [PubMed:10048565 ]

Showing NP-Card for Apicularen A (NP0001562)

MOL for NP0001562 (Apicularen A)

3D MOL for NP0001562 (Apicularen A)

3D SDF for NP0001562 (Apicularen A)

3D-SDF for NP0001562 (Apicularen A)

PDB for NP0001562 (Apicularen A)

3D PDB for NP0001562 (Apicularen A)

SMILES for NP0001562 (Apicularen A)

INCHI for NP0001562 (Apicularen A)

Structure for NP0001562 (Apicularen A)

3D Structure for NP0001562 (Apicularen A)