NP-MRD: Showing NP-Card for Luminacin A1 (NP0003394)

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Record Information

Version

1.0

Created at

2020-12-09 00:39:56 UTC

Updated at

2021-07-15 16:46:19 UTC

NP-MRD ID

NP0003394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luminacin A1

Provided By

NPAtlas

Description

Luminacin A1 belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Luminacin A1 is found in Streptomyces sp. It was first documented in 2000 (PMID: 10966073). Based on a literature review very few articles have been published on Luminacin A1.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117473D          

 63 65  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117473D          

 63 65  0  0  0  0            999 V2000
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    4.8259   -0.6412   -0.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1593   -0.8173   -0.5104 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106   -1.5931   -1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351   -1.5118   -1.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9499   -2.5011   -1.7135 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3969    0.2476   -2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2633   -0.6596   -3.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934   -2.1454   -0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5851   -1.9567   -2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114    0.1537   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.7589   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725    1.2469    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9557    0.9341    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6729    3.0101    2.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0560    2.7381    2.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1946    3.8190    1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125    3.3125   -0.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2598    1.8307   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9544    1.9446   -0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0001   -0.5060   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319   -2.4003   -1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -3.2323   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696   -2.9052    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -3.7614   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -3.6895    0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -4.6473    0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5118   -2.8034    2.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -1.8563    1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012   -1.1090    1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567    1.3980    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121    2.7811   -0.5516 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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5  3  1  0  0  0  0
 24 13  1  0  0  0  0
 30  5  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  0  0  0  0
  2 36  1  0  0  0  0
  3 37  1  6  0  0  0
  6 38  1  6  0  0  0
  7 39  1  0  0  0  0
  8 40  1  0  0  0  0
  8 41  1  0  0  0  0
  9 42  1  6  0  0  0
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 23 53  1  0  0  0  0
 25 54  1  0  0  0  0
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 28 60  1  0  0  0  0
 28 61  1  0  0  0  0
 30 62  1  1  0  0  0
 31 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C(C([H])=C1C(=O)[C@@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])[C@]1([H])O[C@@]([H])(O[H])[C@]2(O[C@@]2([H])C([H])([H])C([H])([H])[H])[C@]([H])(O[H])C1([H])[H])C(=O)C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O8/c1-6-18-23(31-18)17(26)9-16(30-22(23)29)19(10(2)3)21(28)13-7-12(20(27)11(4)5)14(24)8-15(13)25/h7-8,10-11,16-19,22,24-26,29H,6,9H2,1-5H3/t16-,17-,18+,19+,22-,23+/m1/s1

> <INCHI_KEY>
SLMNEPIXQVLESS-RZBOEENUSA-N

> <FORMULA>
C23H32O8

> <MOLECULAR_WEIGHT>
436.501

> <EXACT_MASS>
436.20971799

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.1002366500319

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-[2,4-dihydroxy-5-(2-methylpropanoyl)phenyl]-2-[(2S,3S,4R,6R,8R)-2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl]-3-methylbutan-1-one

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
4.020173302666667

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.404641598764911

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.156190609858739

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3808587790287623

> <JCHEM_POLAR_SURFACE_AREA>
136.82000000000002

> <JCHEM_REFRACTIVITY>
112.0398

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[2,4-dihydroxy-5-(2-methylpropanoyl)phenyl]-2-[(2S,3S,4R,6R,8R)-2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl]-3-methylbutan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
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   -3.3934   -2.1454   -0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0560    2.7381    2.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8125    3.3125   -0.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0001   -0.5060   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3567    1.3980    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121    2.7811   -0.5516 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
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 23 24  2  0
 24 25  1  0
 10 26  1  0
 26 27  1  0
 26 28  1  0
  9 29  1  0
 29 30  1  0
 30 31  1  0
  5  3  1  0
 24 13  1  0
 30  5  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  6
  6 38  1  6
  7 39  1  0
  8 40  1  0
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  9 42  1  6
 10 43  1  6
 14 44  1  0
 18 45  1  1
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 28 59  1  0
 28 60  1  0
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 30 62  1  1
 31 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      -7.115   1.819   1.283  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.935   2.117   0.354  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.632   0.883  -0.430  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.288  -0.228   0.326  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.310   0.298  -0.514  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.959  -0.449  -1.776  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.024  -1.071  -2.377  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.888  -1.491  -1.323  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.759  -0.673  -0.823  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.435  -1.378  -0.775  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.576  -0.398  -0.290  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.063   0.632   0.295  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.001  -0.488  -0.390  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.804   0.435   0.226  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.209   0.395   0.228  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.908   1.456   0.887  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.163   2.336   1.482  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.330   1.700   0.987  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.571   2.934   1.916  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.898   2.210  -0.355  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.826  -0.641  -0.431  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.159  -0.817  -0.510  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.011  -1.593  -1.068  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.635  -1.512  -1.044  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.950  -2.501  -1.714  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.446  -2.528   0.211  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.384  -3.641  -0.059  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.815  -1.996   1.613  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.058   0.025   0.348  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.085   0.919   0.067  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.556   1.929  -0.747  0.00  0.00           O+0
HETATM   32  H   UNK     0      -8.027   1.806   0.648  0.00  0.00           H+0
HETATM   33  H   UNK     0      -7.126   2.635   2.034  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.977   0.833   1.782  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.112   2.436   0.995  0.00  0.00           H+0
HETATM   36  H   UNK     0      -6.288   2.907  -0.340  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.351   0.714  -1.284  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.397   0.248  -2.431  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.263  -0.660  -3.243  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.393  -2.145  -0.621  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.585  -1.957  -2.284  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.611   0.154  -1.590  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.196  -1.759  -1.764  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.272   1.247   0.742  0.00  0.00           H+0
HETATM   45  H   UNK     0       6.956   0.934   1.460  0.00  0.00           H+0
HETATM   46  H   UNK     0       7.673   3.010   2.018  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.056   2.738   2.868  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.195   3.819   1.371  0.00  0.00           H+0
HETATM   49  H   UNK     0       6.813   3.313  -0.436  0.00  0.00           H+0
HETATM   50  H   UNK     0       6.260   1.831  -1.206  0.00  0.00           H+0
HETATM   51  H   UNK     0       7.954   1.945  -0.470  0.00  0.00           H+0
HETATM   52  H   UNK     0       7.000  -0.506  -0.275  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.532  -2.400  -1.582  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.452  -3.232  -2.180  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.570  -2.905   0.341  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.744  -3.761  -1.084  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.245  -3.689   0.659  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.858  -4.647   0.158  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.512  -2.803   2.311  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.893  -1.856   1.723  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.201  -1.109   1.872  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.357   1.398   1.032  0.00  0.00           H+0
HETATM   63  H   UNK     0      -3.012   2.781  -0.552  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   35   36                                             
CONECT    3    2    4    5   37                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    3   30                                             
CONECT    6    5    7    8   38                                             
CONECT    7    6   39                                                       
CONECT    8    6    9   40   41                                             
CONECT    9    8   10   29   42                                             
CONECT   10    9   11   26   43                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15   44                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   45                                             
CONECT   19   18   46   47   48                                             
CONECT   20   18   49   50   51                                             
CONECT   21   15   22   23                                                  
CONECT   22   21   52                                                       
CONECT   23   21   24   53                                                  
CONECT   24   23   25   13                                                  
CONECT   25   24   54                                                       
CONECT   26   10   27   28   55                                             
CONECT   27   26   56   57   58                                             
CONECT   28   26   59   60   61                                             
CONECT   29    9   30                                                       
CONECT   30   29   31    5   62                                             
CONECT   31   30   63                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    2                                                            
CONECT   37    3                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   14                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   30                                                            
CONECT   63   31                                                            
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
   -7.1149    1.8191    1.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9348    2.1170    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6321    0.8830   -0.4301 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2883   -0.2278    0.3257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3096    0.2977   -0.5143 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9587   -0.4489   -1.7760 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0243   -1.0709   -2.3765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8877   -1.4908   -1.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7592   -0.6727   -0.8227 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4352   -1.3776   -0.7748 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5761   -0.3983   -0.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0628    0.6323    0.2947 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0005   -0.4884   -0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8039    0.4347    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2089    0.3954    0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9081    1.4555    0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1633    2.3363    1.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3303    1.6998    0.9873 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5714    2.9345    1.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8983    2.2099   -0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8259   -0.6412   -0.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1593   -0.8173   -0.5104 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0106   -1.5931   -1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6351   -1.5118   -1.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9499   -2.5011   -1.7135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4463   -2.5277    0.2113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3838   -3.6413   -0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145   -1.9955    1.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0575    0.0246    0.3479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0847    0.9191    0.0672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5559    1.9290   -0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0268    1.8063    0.6480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1259    2.6354    2.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9768    0.8331    1.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1124    2.4355    0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2883    2.9074   -0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3508    0.7140   -1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969    0.2476   -2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2633   -0.6596   -3.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3934   -2.1454   -0.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5851   -1.9567   -2.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114    0.1537   -1.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.7589   -1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725    1.2469    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9557    0.9341    1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6729    3.0101    2.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0560    2.7381    2.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1946    3.8190    1.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125    3.3125   -0.4364 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2598    1.8307   -1.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9544    1.9446   -0.4695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0001   -0.5060   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319   -2.4003   -1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -3.2323   -2.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696   -2.9052    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7441   -3.7614   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -3.6895    0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -4.6473    0.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5118   -2.8034    2.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8930   -1.8563    1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012   -1.1090    1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567    1.3980    1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121    2.7811   -0.5516 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 15 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 10 26  1  0
 26 27  1  0
 26 28  1  0
  9 29  1  0
 29 30  1  0
 30 31  1  0
  5  3  1  0
 24 13  1  0
 30  5  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  6
  6 38  1  6
  7 39  1  0
  8 40  1  0
  8 41  1  0
  9 42  1  6
 10 43  1  6
 14 44  1  0
 18 45  1  1
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 23 53  1  0
 25 54  1  0
 26 55  1  1
 27 56  1  0
 27 57  1  0
 27 58  1  0
 28 59  1  0
 28 60  1  0
 28 61  1  0
 30 62  1  1
 31 63  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₈

Average Mass

436.5010 Da

Monoisotopic Mass

436.20972 Da

IUPAC Name

(2S)-1-[2,4-dihydroxy-5-(2-methylpropanoyl)phenyl]-2-[(2S,3S,4R,6R,8R)-2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl]-3-methylbutan-1-one

Traditional Name

(2S)-1-[2,4-dihydroxy-5-(2-methylpropanoyl)phenyl]-2-[(2S,3S,4R,6R,8R)-2-ethyl-4,8-dihydroxy-1,5-dioxaspiro[2.5]octan-6-yl]-3-methylbutan-1-one

CAS Registry Number

Not Available

SMILES

CC[C@@H]1O[C@@]11[C@H](O)C[C@@H](O[C@H]1O)C(C(C)C)C(=O)C1=CC(C(=O)C(C)C)=C(O)C=C1O

InChI Identifier

InChI=1S/C23H32O8/c1-6-18-23(31-18)17(26)9-16(30-22(23)29)19(10(2)3)21(28)13-7-12(20(27)11(4)5)14(24)8-15(13)25/h7-8,10-11,16-19,22,24-26,29H,6,9H2,1-5H3/t16-,17-,18+,19?,22-,23+/m1/s1

InChI Key

SLMNEPIXQVLESS-RZBOEENUSA-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
Streptomyces sp.	NPAtlas	10966073

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Butyrophenone
Phenylpropane
Benzoyl
Aryl alkyl ketone
Resorcinol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Oxane
Benzenoid
Vinylogous acid
Hemiacetal
Secondary alcohol
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
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	2.54	ALOGPS
logP	4.02	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.16	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.04 m³·mol⁻¹	ChemAxon
Polarizability	47.1 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

NPA018460

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015580

Chemspider ID

78438486

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588232

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Naruse N, Kageyama-Kawase R, Funahashi Y, Wakabayashi T: Luminacins: a family of capillary tube formation inhibitors from Streptomyces sp. I. Taxomony, fermentation, isolation, physico-chemical properties and structure elucidation. J Antibiot (Tokyo). 2000 Jun;53(6):579-90. doi: 10.7164/antibiotics.53.579. [PubMed:10966073 ]

Showing NP-Card for Luminacin A1 (NP0003394)

MOL for NP0003394 (Luminacin A1)

3D MOL for NP0003394 (Luminacin A1)

3D SDF for NP0003394 (Luminacin A1)

3D-SDF for NP0003394 (Luminacin A1)

PDB for NP0003394 (Luminacin A1)

3D PDB for NP0003394 (Luminacin A1)

SMILES for NP0003394 (Luminacin A1)

INCHI for NP0003394 (Luminacin A1)

Structure for NP0003394 (Luminacin A1)

3D Structure for NP0003394 (Luminacin A1)