NP-MRD: Showing NP-Card for Granaticin (NP0021719)

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Record Information

Version

2.0

Created at

2021-01-06 06:59:47 UTC

Updated at

2021-07-15 17:37:05 UTC

NP-MRD ID

NP0021719

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Granaticin

Provided By

NPAtlas

Description

Granaticin is found in Streptomyces litmogenes and Streptomyces olivaceus. Granaticin was first documented in 1968 (PMID: 5680736).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105183D          

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M  END

     RDKit          3D

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  Mrv1652306242105183D          

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   -3.8661   -2.2720   -1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014   -0.3102   -2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3805    0.1969   -0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1510   -0.1616   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9451   -1.5014   -1.2777 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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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  2  0  0  0  0
 11 12  1  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
 15 17  2  0  0  0  0
 14 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  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 17  2  1  0  0  0  0
 28 20  1  0  0  0  0
  9  4  1  0  0  0  0
 17 10  1  0  0  0  0
 32 24  1  0  0  0  0
 22 13  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  2 36  1  6  0  0  0
  4 37  1  1  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
  9 40  1  1  0  0  0
 12 41  1  0  0  0  0
 16 42  1  0  0  0  0
 24 43  1  1  0  0  0
 25 44  1  0  0  0  0
 25 45  1  0  0  0  0
 26 46  1  1  0  0  0
 27 47  1  0  0  0  0
 29 48  1  0  0  0  0
 30 49  1  6  0  0  0
 31 50  1  0  0  0  0
 31 51  1  0  0  0  0
 31 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021719

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=C(O[H])C3=C1C(=O)C1=C(C3=O)[C@]3(O[H])[C@]([H])(O[C@@]1([H])C([H])([H])[C@@]3([H])O[H])C([H])([H])[H])[C@@]([H])(O[C@@]1([H])C([H])([H])C(=O)O[C@@]21[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O10/c1-5-11-15(21-8(30-5)4-10(24)32-21)19(27)13-14(17(11)25)20(28)16-12(18(13)26)7-3-9(23)22(16,29)6(2)31-7/h5-9,21,23,25,27,29H,3-4H2,1-2H3/t5-,6+,7-,8-,9+,21+,22-/m0/s1

> <INCHI_KEY>
ONQCWTVJMHJRFM-MRUUKOISSA-N

> <FORMULA>
C22H20O10

> <MOLECULAR_WEIGHT>
444.392

> <EXACT_MASS>
444.105646844

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.018446169421225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,7S,11S,13S,19R,20R,23R)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0^{2,18}.0^{4,16}.0^{6,14}.0^{7,11}]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
0.4588036246666659

> <ALOGPS_LOGS>
-1.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.639191409254687

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.855805067217507

> <JCHEM_PKA_STRONGEST_BASIC>
-3.349143700187958

> <JCHEM_POLAR_SURFACE_AREA>
159.81999999999996

> <JCHEM_REFRACTIVITY>
105.1635

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7S,11S,13S,19R,20R,23R)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0^{2,18}.0^{4,16}.0^{6,14}.0^{7,11}]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 57  0  0  0  0  0  0  0  0999 V2000
    3.7577   -2.7895    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8726   -1.3201   -0.1909 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8701   -0.7997    0.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749    0.5188    0.8696 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2297    1.0897    0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0246    1.3646   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9266    1.6249   -1.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    1.2917   -1.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827    1.3895   -0.0278 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6565    0.7552   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131    1.5670   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6336    2.9094    0.0453 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    0.9618   -0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2270   -0.4402   -0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -1.2295   -0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369   -2.5650   -0.2710 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815   -0.5927   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1043   -1.0750   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2641   -2.3199   -0.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2661   -0.2453   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.0652   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463    1.7564   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515    3.0078    0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5415    1.7607   -0.0457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3205    1.1557    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255   -0.3341    1.0822 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5716   -0.8930    1.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6722   -0.7976   -0.1930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7203   -2.1343   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3494   -0.0084   -1.3228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7859   -0.4384   -1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2225    1.3464   -1.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8143   -3.1421    0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4509   -3.3982   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2109   -3.0234    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -1.2583   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    0.7390    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0567    0.3831    0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3318    2.0507    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9974    2.3883    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604    3.6524    0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720   -3.2684   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4872    2.8346    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512    1.5441    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3668    1.5575    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6731   -0.7060    1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4403   -1.8870    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661   -2.2720   -1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014   -0.3102   -2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3805    0.1969   -0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1510   -0.1616   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9451   -1.5014   -1.2777 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
 30 32  1  0
 17  2  1  0
 28 20  1  0
  9  4  1  0
 17 10  1  0
 32 24  1  0
 22 13  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  4 37  1  1
  5 38  1  0
  5 39  1  0
  9 40  1  1
 12 41  1  0
 16 42  1  0
 24 43  1  1
 25 44  1  0
 25 45  1  0
 26 46  1  1
 27 47  1  0
 29 48  1  0
 30 49  1  6
 31 50  1  0
 31 51  1  0
 31 52  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       3.758  -2.789   0.109  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.873  -1.320  -0.191  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.870  -0.800   0.567  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.875   0.519   0.870  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.230   1.090   0.492  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.025   1.365  -0.949  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.927   1.625  -1.774  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.677   1.292  -1.258  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.983   1.389  -0.028  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.656   0.755  -0.074  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.513   1.567  -0.033  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.634   2.909   0.045  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.276   0.962  -0.073  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.227  -0.440  -0.154  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.350  -1.230  -0.194  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.337  -2.565  -0.271  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.582  -0.593  -0.152  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.104  -1.075  -0.197  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.264  -2.320  -0.269  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.266  -0.245  -0.155  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.222   1.065  -0.079  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.946   1.756  -0.033  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.952   3.008   0.039  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.542   1.761  -0.046  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.321   1.156   1.131  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.325  -0.334   1.082  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.572  -0.893   1.282  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.672  -0.798  -0.193  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.720  -2.134  -0.423  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.349  -0.008  -1.323  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.786  -0.438  -1.479  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.223   1.346  -1.188  0.00  0.00           O+0
HETATM   33  H   UNK     0       4.814  -3.142   0.310  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.451  -3.398  -0.773  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.211  -3.023   1.033  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.210  -1.258  -1.269  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.631   0.739   1.935  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.057   0.383   0.688  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.332   2.051   1.035  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.997   2.388   0.411  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.060   3.652   0.085  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.672  -3.268  -0.315  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.487   2.835   0.010  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.851   1.544   2.057  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.367   1.558   1.124  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.673  -0.706   1.924  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.440  -1.887   1.287  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.866  -2.272  -1.410  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.801  -0.310  -2.248  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.380   0.197  -0.766  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.151  -0.162  -2.489  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.945  -1.501  -1.278  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3   17   36                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    9   37                                             
CONECT    5    4    6   38   39                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10    4   40                                             
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   41                                                       
CONECT   13   11   14   22                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   42                                                       
CONECT   17   15    2   10                                                  
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23   13                                                  
CONECT   23   22                                                            
CONECT   24   21   25   32   43                                             
CONECT   25   24   26   44   45                                             
CONECT   26   25   27   28   46                                             
CONECT   27   26   47                                                       
CONECT   28   26   29   30   20                                             
CONECT   29   28   48                                                       
CONECT   30   28   31   32   49                                             
CONECT   31   30   50   51   52                                             
CONECT   32   30   24                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    2                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    9                                                            
CONECT   41   12                                                            
CONECT   42   16                                                            
CONECT   43   24                                                            
CONECT   44   25                                                            
CONECT   45   25                                                            
CONECT   46   26                                                            
CONECT   47   27                                                            
CONECT   48   29                                                            
CONECT   49   30                                                            
CONECT   50   31                                                            
CONECT   51   31                                                            
CONECT   52   31                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  114    0
END

RDKit          3D

52 57  0  0  0  0  0  0  0  0999 V2000
    3.7577   -2.7895    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8726   -1.3201   -0.1909 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8701   -0.7997    0.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8749    0.5188    0.8696 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2297    1.0897    0.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0246    1.3646   -0.9492 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9266    1.6249   -1.7739 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    1.2917   -1.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827    1.3895   -0.0278 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6565    0.7552   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131    1.5670   -0.0325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6336    2.9094    0.0453 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    0.9618   -0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2270   -0.4402   -0.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500   -1.2295   -0.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3369   -2.5650   -0.2710 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5815   -0.5927   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1043   -1.0750   -0.1969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2641   -2.3199   -0.2692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2661   -0.2453   -0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2218    1.0652   -0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463    1.7564   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9515    3.0078    0.0386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5415    1.7607   -0.0457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3205    1.1557    1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255   -0.3341    1.0822 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5716   -0.8930    1.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6722   -0.7976   -0.1930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7203   -2.1343   -0.4234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3494   -0.0084   -1.3228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7859   -0.4384   -1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2225    1.3464   -1.1883 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8143   -3.1421    0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4509   -3.3982   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2109   -3.0234    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -1.2583   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6314    0.7390    1.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0567    0.3831    0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3318    2.0507    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9974    2.3883    0.4112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0604    3.6524    0.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6720   -3.2684   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4872    2.8346    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512    1.5441    2.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3668    1.5575    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6731   -0.7060    1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4403   -1.8870    1.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8661   -2.2720   -1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014   -0.3102   -2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3805    0.1969   -0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1510   -0.1616   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9451   -1.5014   -1.2777 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 14 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  6
 28 30  1  0
 30 31  1  0
 30 32  1  0
 17  2  1  0
 28 20  1  0
  9  4  1  0
 17 10  1  0
 32 24  1  0
 22 13  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  6
  4 37  1  1
  5 38  1  0
  5 39  1  0
  9 40  1  1
 12 41  1  0
 16 42  1  0
 24 43  1  1
 25 44  1  0
 25 45  1  0
 26 46  1  1
 27 47  1  0
 29 48  1  0
 30 49  1  6
 31 50  1  0
 31 51  1  0
 31 52  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₁₀

Average Mass

444.3920 Da

Monoisotopic Mass

444.10565 Da

IUPAC Name

(1S,7S,11S,13S,19R,20R,23R)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0^{2,18}.0^{4,16}.0^{6,14}.0^{7,11}]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

Traditional Name

(1S,7S,11S,13S,19R,20R,23R)-5,15,19,23-tetrahydroxy-13,20-dimethyl-8,12,21-trioxahexacyclo[17.2.2.0^{2,18}.0^{4,16}.0^{6,14}.0^{7,11}]tricosa-2(18),4(16),5,14-tetraene-3,9,17-trione

CAS Registry Number

Not Available

SMILES

CC1O[C@H]2CC(=O)O[C@H]2C2=C(O)C3=C(C(O)=C12)C(=O)C1=C([C@@H]2C[C@@H](O)[C@@]1(O)[C@@H](C)O2)C3=O

InChI Identifier

InChI=1S/C22H20O10/c1-5-11-15(21-8(30-5)4-10(24)32-21)19(27)13-14(17(11)25)20(28)16-12(18(13)26)7-3-9(23)22(16,29)6(2)31-7/h5-9,21,23,25,27,29H,3-4H2,1-2H3/t5?,6-,7+,8+,9?,21-,22+/m1/s1

InChI Key

ONQCWTVJMHJRFM-MRUUKOISSA-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 litmogenes	Bacteria	KNApSAcK
Streptomyces olivaceus	NPAtlas	5680736

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	1.44	ALOGPS
logP	0.46	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	105.16 m³·mol⁻¹	ChemAxon
Polarizability	43.02 Å³	ChemAxon
Number of Rings	6	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

Not Available

References

General References

Keller-Schierlein W, Brufani M, Barcza S: [The structure of granaticin and of granaticin B. 1. Spectroscopic charcteristics and chemical analysis]. Helv Chim Acta. 1968;51(6):1257-68. doi: 10.1002/hlca.19680510609. [PubMed:5680736 ]

Showing NP-Card for Granaticin (NP0021719)

MOL for NP0021719 (Granaticin)

3D MOL for NP0021719 (Granaticin)

3D SDF for NP0021719 (Granaticin)

3D-SDF for NP0021719 (Granaticin)

PDB for NP0021719 (Granaticin)

3D PDB for NP0021719 (Granaticin)

SMILES for NP0021719 (Granaticin)

INCHI for NP0021719 (Granaticin)

Structure for NP0021719 (Granaticin)

3D Structure for NP0021719 (Granaticin)