NP-MRD: Showing NP-Card for emodin 6-apioside. frangulin B (NP0030514)

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Record Information

Version

2.0

Created at

2021-06-19 21:51:15 UTC

Updated at

2021-08-20 00:00:18 UTC

NP-MRD ID

NP0030514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

emodin 6-apioside. frangulin B

Provided By

JEOL Database JEOL Logo

Description

3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1,8-dihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. emodin 6-apioside. frangulin B is found in Frangula alnus, frangula Rhamnus and Rhamnus formosana. emodin 6-apioside. frangulin B was first documented in 1998 (Francis, G. W., et al.). Based on a literature review very few articles have been published on 3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1,8-dihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123513D          

 47 50  0  0  0  0            999 V2000
    5.8646   -3.6558    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743   -2.6321    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352   -2.1782   -0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3891   -1.2500   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296   -0.8591   -2.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616   -0.7665   -0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -1.2257    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387   -2.1594    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -0.7370    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5759   -1.1319    2.2617 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0348    2.1031    3.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643    1.8883    1.1435 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.8200    2.0779   -0.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3034    1.6264   -1.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
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 26 47  1  0  0  0  0
M  END

     RDKit          3D

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    5.2352   -2.1782   -0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192123513D          

 47 50  0  0  0  0            999 V2000
    5.8646   -3.6558    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
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 13 12  1  0  0  0  0
  2  1  1  0  0  0  0
 12 11  2  0  0  0  0
 25 26  1  0  0  0  0
 13 14  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 19 40  1  0  0  0  0
 20 41  1  0  0  0  0
 20 42  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 15 37  1  1  0  0  0
 22 44  1  6  0  0  0
 23 45  1  0  0  0  0
 21 43  1  0  0  0  0
 24 46  1  0  0  0  0
 12 36  1  0  0  0  0
  8 35  1  0  0  0  0
  3 33  1  0  0  0  0
  5 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 26 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C2=C1C(=O)C1=C(O[H])C([H])=C(O[C@]3([H])OC([H])([H])[C@](O[H])(C([H])([H])O[H])[C@@]3([H])O[H])C([H])=C1C2=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O9/c1-8-2-10-14(12(22)3-8)17(25)15-11(16(10)24)4-9(5-13(15)23)29-19-18(26)20(27,6-21)7-28-19/h2-5,18-19,21-23,26-27H,6-7H2,1H3/t18-,19-,20+/m0/s1

> <INCHI_KEY>
AEQMIFRODRFTJF-SLFFLAALSA-N

> <FORMULA>
C20H18O9

> <MOLECULAR_WEIGHT>
402.355

> <EXACT_MASS>
402.09508216

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
39.877443366777996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1,8-dihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
2.0476999913333334

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.541096066930406

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.861311702879519

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423881608652353

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
98.5362

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
frangulin B

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    5.8646   -3.6558    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743   -2.6321    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352   -2.1782   -0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3891   -1.2500   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296   -0.8591   -2.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616   -0.7665   -0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -1.2257    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387   -2.1594    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -0.7370    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5759   -1.1319    2.2617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994    0.2365    0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    0.6884    1.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969    1.6138    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314    2.1327    1.1399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5415    1.7797    2.4931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9743    0.4051    2.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3681    0.3877    2.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9220    1.7717    2.6096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0348    2.1031    3.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643    1.8883    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5919    1.1646    0.9888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7238    2.6484    2.9464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6823    2.8680    4.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8200    2.0779   -0.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3034    1.6264   -1.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    2.1377   -2.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1723    0.7015   -0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621    0.2146   -1.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6023    0.6272   -2.6631 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8834   -3.5303    2.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5058   -4.6627    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8953   -3.5551    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1012   -2.5440   -1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -0.2059   -3.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -2.5187    2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4289    0.2908    2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769    1.9370    3.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8648   -0.4162    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4547    0.1511    3.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8057    1.6690    3.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6307    1.4828    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5740    2.9319    0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8335    1.2219    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565    3.6310    2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6231    2.9093    4.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840    2.7978   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3078    1.7472   -3.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 25  2  0
 27 11  1  0
 15 14  1  0
 22 23  1  0
 27 28  1  0
 11  9  1  0
  9  7  1  0
  6 28  1  0
  6  7  2  0
 15 16  1  0
 20 21  1  0
 24 13  2  0
 18 22  1  0
 22 15  1  0
  6  4  1  0
  7  8  1  0
  8  2  2  0
  2  3  1  0
  3  4  2  0
 16 17  1  0
 28 29  2  0
 17 18  1  0
  9 10  2  0
 24 25  1  0
  4  5  1  0
 13 12  1  0
  2  1  1  0
 12 11  2  0
 25 26  1  0
 13 14  1  0
 18 19  1  1
 18 20  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 17 38  1  0
 17 39  1  0
 15 37  1  1
 22 44  1  6
 23 45  1  0
 21 43  1  0
 24 46  1  0
 12 36  1  0
  8 35  1  0
  3 33  1  0
  5 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 26 47  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       5.865  -3.656   0.973  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.974  -2.632   0.333  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.235  -2.178  -0.965  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.389  -1.250  -1.571  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.730  -0.859  -2.838  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.262  -0.767  -0.896  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.988  -1.226   0.391  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.839  -2.159   1.002  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.803  -0.737   1.125  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.576  -1.132   2.262  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.899   0.237   0.478  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.236   0.688   1.173  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.097   1.614   0.583  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.231   2.133   1.140  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.542   1.780   2.493  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.974   0.405   2.582  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.368   0.388   2.925  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.922   1.772   2.610  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.035   2.103   3.457  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.364   1.888   1.143  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.592   1.165   0.989  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.724   2.648   2.946  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.682   2.868   4.369  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.820   2.078  -0.705  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.303   1.626  -1.395  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.489   2.138  -2.651  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.172   0.702  -0.807  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.362   0.215  -1.529  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.602   0.627  -2.663  0.00  0.00           O+0
HETATM   30  H   UNK     0       5.883  -3.530   2.061  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.506  -4.663   0.739  0.00  0.00           H+0
HETATM   32  H   UNK     0       6.895  -3.555   0.617  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.101  -2.544  -1.514  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.066  -0.206  -3.151  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.614  -2.519   2.007  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.429   0.291   2.167  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.677   1.937   3.150  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.865  -0.416   2.373  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.455   0.151   3.992  0.00  0.00           H+0
HETATM   40  H   UNK     0      -6.806   1.669   3.031  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.631   1.483   0.442  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.574   2.932   0.887  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.833   1.222   0.046  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.757   3.631   2.466  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.623   2.909   4.645  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.484   2.798  -1.178  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.308   1.747  -3.029  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    8    3    1                                                  
CONECT    3    2    4   33                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4   34                                                       
CONECT    6   28    7    4                                                  
CONECT    7    9    6    8                                                  
CONECT    8    7    2   35                                                  
CONECT    9   11    7   10                                                  
CONECT   10    9                                                            
CONECT   11   27    9   12                                                  
CONECT   12   13   11   36                                                  
CONECT   13   24   12   14                                                  
CONECT   14   15   13                                                       
CONECT   15   14   16   22   37                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   38   39                                             
CONECT   18   22   17   19   20                                             
CONECT   19   18   40                                                       
CONECT   20   21   18   41   42                                             
CONECT   21   20   43                                                       
CONECT   22   23   18   15   44                                             
CONECT   23   22   45                                                       
CONECT   24   13   25   46                                                  
CONECT   25   27   24   26                                                  
CONECT   26   25   47                                                       
CONECT   27   25   11   28                                                  
CONECT   28   27    6   29                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    5                                                            
CONECT   35    8                                                            
CONECT   36   12                                                            
CONECT   37   15                                                            
CONECT   38   17                                                            
CONECT   39   17                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   20                                                            
CONECT   43   21                                                            
CONECT   44   22                                                            
CONECT   45   23                                                            
CONECT   46   24                                                            
CONECT   47   26                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

RDKit          3D

47 50  0  0  0  0  0  0  0  0999 V2000
    5.8646   -3.6558    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743   -2.6321    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352   -2.1782   -0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3891   -1.2500   -1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296   -0.8591   -2.8378 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2616   -0.7665   -0.8958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9883   -1.2257    0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8387   -2.1594    1.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -0.7370    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5759   -1.1319    2.2617 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994    0.2365    0.4780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    0.6884    1.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969    1.6138    0.5831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314    2.1327    1.1399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5415    1.7797    2.4931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9743    0.4051    2.5823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3681    0.3877    2.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9220    1.7717    2.6096 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0348    2.1031    3.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3643    1.8883    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5919    1.1646    0.9888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7238    2.6484    2.9464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6823    2.8680    4.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8200    2.0779   -0.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3034    1.6264   -1.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888    2.1377   -2.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1723    0.7015   -0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621    0.2146   -1.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6023    0.6272   -2.6631 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8834   -3.5303    2.0611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5058   -4.6627    0.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8953   -3.5551    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1012   -2.5440   -1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -0.2059   -3.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -2.5187    2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4289    0.2908    2.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6769    1.9370    3.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8648   -0.4162    2.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4547    0.1511    3.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8057    1.6690    3.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6307    1.4828    0.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5740    2.9319    0.8869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8335    1.2219    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565    3.6310    2.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6231    2.9093    4.6446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4840    2.7978   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3078    1.7472   -3.0294 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 25  2  0
 27 11  1  0
 15 14  1  0
 22 23  1  0
 27 28  1  0
 11  9  1  0
  9  7  1  0
  6 28  1  0
  6  7  2  0
 15 16  1  0
 20 21  1  0
 24 13  2  0
 18 22  1  0
 22 15  1  0
  6  4  1  0
  7  8  1  0
  8  2  2  0
  2  3  1  0
  3  4  2  0
 16 17  1  0
 28 29  2  0
 17 18  1  0
  9 10  2  0
 24 25  1  0
  4  5  1  0
 13 12  1  0
  2  1  1  0
 12 11  2  0
 25 26  1  0
 13 14  1  0
 18 19  1  1
 18 20  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 17 38  1  0
 17 39  1  0
 15 37  1  1
 22 44  1  6
 23 45  1  0
 21 43  1  0
 24 46  1  0
 12 36  1  0
  8 35  1  0
  3 33  1  0
  5 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 26 47  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₉

Average Mass

402.3550 Da

Monoisotopic Mass

402.09508 Da

IUPAC Name

3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-1,8-dihydroxy-6-methyl-9,10-dihydroanthracene-9,10-dione

Traditional Name

frangulin B

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C([H])C2=C1C(=O)C1=C(O[H])C([H])=C(O[C@]3([H])OC([H])([H])[C@](O[H])(C([H])([H])O[H])[C@@]3([H])O[H])C([H])=C1C2=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C20H18O9/c1-8-2-10-14(12(22)3-8)17(25)15-11(16(10)24)4-9(5-13(15)23)29-19-18(26)20(27,6-21)7-28-19/h2-5,18-19,21-23,26-27H,6-7H2,1H3/t18-,19-,20+/m0/s1

InChI Key

AEQMIFRODRFTJF-SLFFLAALSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6 , simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Frangula alnus	LOTUS Database	35616633
frangula Rhamnus	JEOL database	Francis, G. W., et al, Magn. Reson. Chem. 36, 769 (1998)
Rhamnus cathartica	KNApSAcK Database	22123792
Rhamnus formosana	LOTUS Database	35616633
Rhamnus frangula	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Pentose monosaccharide
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Vinylogous acid
Tetrahydrofuran
Tertiary alcohol
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

anthraquinone (CHEBI:5168 )
Anthraquinone type (C10349 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	774.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	7.09 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.660 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.91	ALOGPS
logP	2.05	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.54 m³·mol⁻¹	ChemAxon
Polarizability	39.88 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002825

Chemspider ID

391087

KEGG Compound ID

C10349

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

Not Available

Good Scents ID

rw1700701

References

General References

Francis, G. W., et al. (1998). Francis, G. W., et al, Magn. Reson. Chem. 36, 769 (1998). Mag. Reson. Chem..

Showing NP-Card for emodin 6-apioside. frangulin B (NP0030514)

MOL for NP0030514 (emodin 6-apioside. frangulin B)

3D MOL for NP0030514 (emodin 6-apioside. frangulin B)

3D SDF for NP0030514 (emodin 6-apioside. frangulin B)

3D-SDF for NP0030514 (emodin 6-apioside. frangulin B)

PDB for NP0030514 (emodin 6-apioside. frangulin B)

3D PDB for NP0030514 (emodin 6-apioside. frangulin B)

SMILES for NP0030514 (emodin 6-apioside. frangulin B)

INCHI for NP0030514 (emodin 6-apioside. frangulin B)

Structure for NP0030514 (emodin 6-apioside. frangulin B)

3D Structure for NP0030514 (emodin 6-apioside. frangulin B)