NP-MRD: Showing NP-Card for Aigialomycin A (NP0004068)

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Record Information

Version

1.0

Created at

2020-12-09 01:34:07 UTC

Updated at

2021-07-15 16:48:08 UTC

NP-MRD ID

NP0004068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aigialomycin A

Provided By

NPAtlas

Description

Hypothemycin 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. Aigialomycin A is found in Aigialus and Aigialus parvus. It was first documented in 1999 (PMID: 10421424). Based on a literature review a significant number of articles have been published on hypothemycin (PMID: 11871887) (PMID: 10595743) (PMID: 10598882) (PMID: 17691074).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118033D          

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     RDKit          3D

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 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
  9  3  1  0  0  0  0
 12 10  1  0  0  0  0
 26  7  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  4 31  1  0  0  0  0
  6 32  1  0  0  0  0
  9 33  1  0  0  0  0
 10 34  1  1  0  0  0
 12 35  1  6  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 14 38  1  1  0  0  0
 15 39  1  0  0  0  0
 16 40  1  1  0  0  0
 17 41  1  0  0  0  0
 20 42  1  0  0  0  0
 21 43  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 23 46  1  1  0  0  0
 24 47  1  0  0  0  0
 24 48  1  0  0  0  0
 24 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004068

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/b5-3-/t9-,14-,15+,17+,18+/m0/s1

> <INCHI_KEY>
SSNQAUBBJYCSMY-KNTMUCJRSA-N

> <FORMULA>
C19H22O8

> <MOLECULAR_WEIGHT>
378.3732

> <EXACT_MASS>
378.13146768

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.41962207548021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,4R,6S,7S,9Z,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(19),9,15,17-tetraene-8,14-dione

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
1.6343301726666666

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.425224435229335

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.474741354591858

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2662629454875995

> <JCHEM_POLAR_SURFACE_AREA>
125.82000000000002

> <JCHEM_REFRACTIVITY>
94.9755

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4R,6S,7S,9Z,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(19),9,15,17-tetraene-8,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
    6.2671   -0.7415   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517   -1.3787   -0.8724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785   -0.7451   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0982    0.5518    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    1.1648    0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2420    2.4872    1.2719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    0.4989    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175   -0.7926    0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -1.4073    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484   -1.6847    0.8533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4604   -1.0872    1.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076   -1.2791    0.2062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6024   -2.4367   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9879   -2.3512    0.3800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9316   -2.9791   -0.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4185   -0.9092    0.6225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4635   -0.9062    1.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246   -0.2836   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1905   -0.3985   -0.8141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1731    0.4319   -1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4695    1.5226   -1.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466    2.1860   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8994    2.4076    0.3076 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0092    2.4313   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007    1.5165    1.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7700    1.2636    1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    1.7082    2.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2485   -0.0586   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0171   -1.5356   -1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6547   -0.2324   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0242    1.1164    0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5024    2.9767    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -2.4242   -0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150   -2.7793    0.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.4983   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223   -3.4217    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -2.4531   -1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0100   -2.8614    1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277   -3.9691   -0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5865   -0.4204    1.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1796   -0.2755    1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864    0.0421   -2.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9407    1.9636   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    1.7713    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8245    3.2189   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8809    3.4824    0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.5735   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    3.3089   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0231    2.6862   -0.5525 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
  9  3  1  0
 12 10  1  0
 26  7  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  1
 12 35  1  6
 13 36  1  0
 13 37  1  0
 14 38  1  1
 15 39  1  0
 16 40  1  1
 17 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  1
 24 47  1  0
 24 48  1  0
 24 49  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       6.267  -0.742  -1.115  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.052  -1.379  -0.872  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.978  -0.745  -0.216  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.098   0.552   0.217  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.031   1.165   0.863  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.242   2.487   1.272  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.824   0.499   1.090  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.718  -0.793   0.657  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.795  -1.407   0.005  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.548  -1.685   0.853  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.460  -1.087   1.560  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.708  -1.279   0.206  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.602  -2.437  -0.179  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.988  -2.351   0.380  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.932  -2.979  -0.431  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.418  -0.909   0.623  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.463  -0.906   1.578  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.925  -0.284  -0.612  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.191  -0.399  -0.814  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.173   0.432  -1.612  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.470   1.523  -1.399  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.347   2.186  -0.080  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.899   2.408   0.308  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.009   2.431  -0.900  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.501   1.517   1.314  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.770   1.264   1.777  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.162   1.708   2.929  0.00  0.00           O+0
HETATM   28  H   UNK     0       6.248  -0.059  -1.989  0.00  0.00           H+0
HETATM   29  H   UNK     0       7.017  -1.536  -1.367  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.655  -0.232  -0.200  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.024   1.116   0.063  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.502   2.977   1.718  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.741  -2.424  -0.350  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.715  -2.779   0.916  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.613  -0.498  -0.539  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.122  -3.422   0.094  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.669  -2.453  -1.284  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.010  -2.861   1.366  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.928  -3.969  -0.310  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.587  -0.420   1.112  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.180  -0.276   1.298  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.186   0.042  -2.667  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.941   1.964  -2.248  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.980   1.771   0.691  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.825   3.219  -0.276  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.881   3.482   0.677  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.066   1.573  -1.560  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.357   3.309  -1.515  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.023   2.686  -0.553  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   32                                                       
CONECT    7    5    8   26                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3   33                                                  
CONECT   10    8   11   12   34                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   10   35                                             
CONECT   13   12   14   36   37                                             
CONECT   14   13   15   16   38                                             
CONECT   15   14   39                                                       
CONECT   16   14   17   18   40                                             
CONECT   17   16   41                                                       
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   42                                                  
CONECT   21   20   22   43                                                  
CONECT   22   21   23   44   45                                             
CONECT   23   22   24   25   46                                             
CONECT   24   23   47   48   49                                             
CONECT   25   23   26                                                       
CONECT   26   25   27    7                                                  
CONECT   27   26                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    6                                                            
CONECT   33    9                                                            
CONECT   34   10                                                            
CONECT   35   12                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   20                                                            
CONECT   43   21                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   23                                                            
CONECT   47   24                                                            
CONECT   48   24                                                            
CONECT   49   24                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  102    0
END

RDKit          3D

49 51  0  0  0  0  0  0  0  0999 V2000
    6.2671   -0.7415   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517   -1.3787   -0.8724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9785   -0.7451   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0982    0.5518    0.2174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0307    1.1648    0.8632 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2420    2.4872    1.2719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236    0.4989    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175   -0.7926    0.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7950   -1.4073    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484   -1.6847    0.8533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4604   -1.0872    1.5600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076   -1.2791    0.2062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6024   -2.4367   -0.1792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9879   -2.3512    0.3800 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9316   -2.9791   -0.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4185   -0.9092    0.6225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4635   -0.9062    1.5780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246   -0.2836   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1905   -0.3985   -0.8141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1731    0.4319   -1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4695    1.5226   -1.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466    2.1860   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8994    2.4076    0.3076 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0092    2.4313   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5007    1.5165    1.3136 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7700    1.2636    1.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    1.7082    2.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2485   -0.0586   -1.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0171   -1.5356   -1.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6547   -0.2324   -0.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0242    1.1164    0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5024    2.9767    1.7178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7408   -2.4242   -0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150   -2.7793    0.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134   -0.4983   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223   -3.4217    0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -2.4531   -1.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0100   -2.8614    1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9277   -3.9691   -0.3103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5865   -0.4204    1.1117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1796   -0.2755    1.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864    0.0421   -2.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9407    1.9636   -2.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    1.7713    0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8245    3.2189   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8809    3.4824    0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.5735   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3570    3.3089   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0231    2.6862   -0.5525 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  2  0
  9  3  1  0
 12 10  1  0
 26  7  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  9 33  1  0
 10 34  1  1
 12 35  1  6
 13 36  1  0
 13 37  1  0
 14 38  1  1
 15 39  1  0
 16 40  1  1
 17 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  1
 24 47  1  0
 24 48  1  0
 24 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₈

Average Mass

378.3732 Da

Monoisotopic Mass

378.13147 Da

IUPAC Name

(2R,4R,6S,7S,9Z,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(19),9,15,17-tetraene-8,14-dione

Traditional Name

(2R,4R,6S,7S,9Z,12S)-6,7,16-trihydroxy-18-methoxy-12-methyl-3,13-dioxatricyclo[13.4.0.0^{2,4}]nonadeca-1(19),9,15,17-tetraene-8,14-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=C1)[C@H]1O[C@@H]1C[C@H](O)[C@H](O)C(=O)\C=C/C[C@H](C)OC2=O

InChI Identifier

InChI=1S/C19H22O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/b5-3-/t9-,14-,15+,17+,18+/m0/s1

InChI Key

SSNQAUBBJYCSMY-KNTMUCJRSA-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
Aigialus	NPAtlas	11871887
Aigialus parvus	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Zearalenones

Direct Parent

Zearalenones

Alternative Parents

Substituents

Zearalenone-skeleton
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
1,2-diol
Carboxylic acid ester
Ketone
Cyclic ketone
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:83275 )
epoxide (CHEBI:83275 )
phenols (CHEBI:83275 )
enone (CHEBI:83275 )
diol (CHEBI:83275 )
polyketide (CHEBI:83275 )
macrolide (CHEBI:83275 )

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	0.95	ALOGPS
logP	1.63	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.47	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	125.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.98 m³·mol⁻¹	ChemAxon
Polarizability	37.42 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	No	ChemAxon

External Links

NPAtlas ID

NPA011633

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8105274

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

83275

Good Scents ID

Not Available

References

General References

Isaka M, Suyarnsestakorn C, Tanticharoen M, Kongsaeree P, Thebtaranonth Y: Aigialomycins A-E, new resorcylic macrolides from the marine mangrove fungus Aigialus parvus. J Org Chem. 2002 Mar 8;67(5):1561-6. doi: 10.1021/jo010930g. [PubMed:11871887 ]
Sonoda H, Omi K, Hojo K, Nishida K, Omura S, Sugita K: Suppression of oncogenic transformation by hypothemycin associated with accelerated cyclin D1 degradation through ubiquitin-proteasome pathway. Life Sci. 1999;65(4):381-94. doi: 10.1016/s0024-3205(99)00259-3. [PubMed:10421424 ]
Tanaka H, Nishida K, Sugita K, Yoshioka T: Antitumor efficacy of hypothemycin, a new Ras-signaling inhibitor. Jpn J Cancer Res. 1999 Oct;90(10):1139-45. doi: 10.1111/j.1349-7006.1999.tb00688.x. [PubMed:10595743 ]
Camacho R, Staruch MJ, DaSilva C, Koprak S, Sewell T, Salituro G, Dumont FJ: Hypothemycin inhibits the proliferative response and modulates the production of cytokines during T cell activation. Immunopharmacology. 1999 Nov;44(3):255-65. doi: 10.1016/s0162-3109(99)00085-5. [PubMed:10598882 ]
Hearn BR, Sundermann K, Cannoy J, Santi DV: Semisynthesis and cytotoxicity of hypothemycin analogues. ChemMedChem. 2007 Nov;2(11):1598-600. doi: 10.1002/cmdc.200700128. [PubMed:17691074 ]

Showing NP-Card for Aigialomycin A (NP0004068)

MOL for NP0004068 (Aigialomycin A)

3D MOL for NP0004068 (Aigialomycin A)

3D SDF for NP0004068 (Aigialomycin A)

3D-SDF for NP0004068 (Aigialomycin A)

PDB for NP0004068 (Aigialomycin A)

3D PDB for NP0004068 (Aigialomycin A)

SMILES for NP0004068 (Aigialomycin A)

INCHI for NP0004068 (Aigialomycin A)

Structure for NP0004068 (Aigialomycin A)

3D Structure for NP0004068 (Aigialomycin A)