NP-MRD: Showing NP-Card for KHAINAOSIDE A (NP0001535)

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Record Information

Version

2.0

Created at

2020-08-26 23:17:50 UTC

Updated at

2021-08-10 02:55:04 UTC

NP-MRD ID

NP0001535

Secondary Accession Numbers

None

Natural Product Identification

Common Name

KHAINAOSIDE A

Description

(2S,3R,4S,5S,6R)-2-{5-[(1R,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-hexahydrofuro[3,4-c]furan-1-yl]-2-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. KHAINAOSIDE A is found in Vitex glabrata. Based on a literature review very few articles have been published on (2S,3R,4S,5S,6R)-2-{5-[(1R,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-hexahydrofuro[3,4-c]furan-1-yl]-2-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652308272001172D          

 66 71  0  0  1  0            999 V2000
    7.3363   -2.3520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -2.7645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1929   -2.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1929   -3.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9074   -4.0020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1929   -4.4145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -3.5895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0508   -4.4145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4  5  1  0  0  0  0
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  8  9  1  0  0  0  0
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  9 16  1  0  0  0  0
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 63 64  1  0  0  0  0
 63 65  2  0  0  0  0
 53 65  1  0  0  0  0
 65 66  1  0  0  0  0
M  END

NP0001535
     RDKit          3D

 66 71  0  0  0  0  0  0  0  0999 V2000
   -6.2803    1.8907   -2.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6271    1.0639   -1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2344   -0.3593   -1.5281 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.4888    0.6582   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109    1.3313    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652308272001172D          

 66 71  0  0  1  0            999 V2000
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    5.9074   -5.6520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7845    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8277    1.5218    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9001    0.5778    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6777   -0.2941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4847   -0.4656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8678    0.0326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3569    1.9103    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740    2.6548    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  1  1  0  0  0
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  9 16  1  0  0  0  0
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  6 24  1  0  0  0  0
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  4 28  1  0  0  0  0
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 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
  3 33  1  0  0  0  0
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 65 66  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001535

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC([H])([H])[C@]2(O[H])[C@]([H])(OC([H])([H])[C@]12O[H])C1=C([H])C2=C(OC([H])([H])O2)C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O13/c26-7-17-18(28)19(29)20(30)23(38-17)37-15-5-11(1-3-13(15)27)21-24(31)8-34-22(25(24,32)9-33-21)12-2-4-14-16(6-12)36-10-35-14/h1-6,17-23,26-32H,7-10H2/t17-,18-,19+,20-,21-,22-,23-,24+,25+/m1/s1

> <INCHI_KEY>
HUVQMIPFAVBQIA-KYBLTUFESA-N

> <FORMULA>
C25H28O13

> <MOLECULAR_WEIGHT>
536.486

> <EXACT_MASS>
536.152990962

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.77980718443759

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{5-[(1R,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-hexahydrofuro[3,4-c]furan-1-yl]-2-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
-1.362093311

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.423462606277138

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.743559061576342

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549076875

> <JCHEM_POLAR_SURFACE_AREA>
196.98999999999995

> <JCHEM_REFRACTIVITY>
122.2609

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{5-[(1R,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-tetrahydrofuro[3,4-c]furan-1-yl]-2-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001535
     RDKit          3D

 66 71  0  0  0  0  0  0  0  0999 V2000
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 37 65  1  1
 38 66  1  0
M  END

HEADER    PROTEIN                                 27-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-AUG-20         0                                  
HETATM    1  H   UNK     0      13.694  -4.390   0.000  0.00  0.00           H+0
HETATM    2  O   UNK     0      12.361  -5.160   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.027  -4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.693  -5.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.693  -6.700   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.027  -7.470   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       9.693  -8.240   0.000  0.00  0.00           H+0
HETATM    8  O   UNK     0      12.361  -6.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.694  -7.470   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      15.028  -8.240   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      15.028  -6.700   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      15.719  -5.324   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0      14.337  -5.324   0.000  0.00  0.00           H+0
HETATM   14  O   UNK     0      16.362  -7.470   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0      17.902  -7.470   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0      13.694  -9.010   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      13.694 -10.550   0.000  0.00  0.00           H+0
HETATM   18  O   UNK     0      15.028  -9.780   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      16.362 -10.550   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0      12.361  -9.780   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      11.027 -10.550   0.000  0.00  0.00           H+0
HETATM   22  O   UNK     0      12.361 -11.320   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      12.361 -12.860   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      11.027  -9.010   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      12.361  -8.240   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0       9.693  -9.780   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       8.360 -10.550   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       8.360  -4.390   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       7.026  -5.160   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       8.360  -2.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.693  -2.080   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      10.604  -0.839   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0      11.027  -2.850   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      12.361  -2.080   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0       7.026  -2.080   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0       6.945  -3.618   0.000  0.00  0.00           H+0
HETATM   37  O   UNK     0       5.619  -2.707   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.589  -1.562   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0       3.077  -1.856   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.705  -2.824   0.000  0.00  0.00           H+0
HETATM   41  C   UNK     0       5.359  -0.229   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.852   0.091   0.000  0.00  0.00           O+0
HETATM   43  H   UNK     0       2.603  -0.808   0.000  0.00  0.00           H+0
HETATM   44  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   45  H   UNK     0       5.278   2.841   0.000  0.00  0.00           H+0
HETATM   46  O   UNK     0       6.605   1.929   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       7.635   0.785   0.000  0.00  0.00           C+0
HETATM   48  H   UNK     0       9.147   1.079   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0       8.518   2.046   0.000  0.00  0.00           H+0
HETATM   50  C   UNK     0       6.865  -0.549   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       8.371  -0.869   0.000  0.00  0.00           O+0
HETATM   52  H   UNK     0       9.621   0.031   0.000  0.00  0.00           H+0
HETATM   53  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   55  H   UNK     0       1.620   0.061   0.000  0.00  0.00           H+0
HETATM   56  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   60  H   UNK     0      -2.533   3.566   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.533   2.120   0.000  0.00  0.00           H+0
HETATM   62  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   64  H   UNK     0       2.530   5.923   0.000  0.00  0.00           H+0
HETATM   65  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   66  H   UNK     0       4.618   4.956   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   24                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16    9   17   18   20                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   16   21   22   24                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   20    6   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28    4   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33                                                            
CONECT   35   30   36   37   50                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38   42   44   50                                             
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   41   45   46   53                                             
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   49   50                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   47   35   41   51                                             
CONECT   51   50   52                                                       
CONECT   52   51                                                            
CONECT   53   44   54   65                                                  
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57   62                                                  
CONECT   57   56   58   63                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60   61   62                                             
CONECT   60   59                                                            
CONECT   61   59                                                            
CONECT   62   59   56                                                       
CONECT   63   57   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   53   66                                                  
CONECT   66   65                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  142    0
END

COMPND    NP0001535
HETATM    1  O1  UNL     1      -6.280   1.891  -2.374  1.00  0.00           O  
HETATM    2  C1  UNL     1      -6.627   1.064  -1.297  1.00  0.00           C  
HETATM    3  C2  UNL     1      -6.234  -0.359  -1.528  1.00  0.00           C  
HETATM    4  O2  UNL     1      -4.905  -0.587  -1.721  1.00  0.00           O  
HETATM    5  C3  UNL     1      -4.139  -0.744  -0.570  1.00  0.00           C  
HETATM    6  O3  UNL     1      -3.918   0.461   0.104  1.00  0.00           O  
HETATM    7  C4  UNL     1      -2.714   1.095   0.297  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.489   0.658  -0.148  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.311   1.331   0.073  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.002   0.854  -0.410  1.00  0.00           C  
HETATM   11  O4  UNL     1       1.670   1.924  -0.962  1.00  0.00           O  
HETATM   12  C8  UNL     1       3.015   1.761  -0.773  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.244   0.718   0.266  1.00  0.00           C  
HETATM   14  O5  UNL     1       3.972   1.174   1.360  1.00  0.00           O  
HETATM   15  C10 UNL     1       3.826  -0.539  -0.326  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.304  -0.513  -0.367  1.00  0.00           C  
HETATM   17  C12 UNL     1       5.941  -0.430  -1.587  1.00  0.00           C  
HETATM   18  C13 UNL     1       7.319  -0.406  -1.621  1.00  0.00           C  
HETATM   19  C14 UNL     1       8.113  -0.462  -0.495  1.00  0.00           C  
HETATM   20  C15 UNL     1       7.466  -0.545   0.720  1.00  0.00           C  
HETATM   21  C16 UNL     1       6.082  -0.570   0.771  1.00  0.00           C  
HETATM   22  O6  UNL     1       8.478  -0.586   1.674  1.00  0.00           O  
HETATM   23  C17 UNL     1       9.691  -0.954   1.038  1.00  0.00           C  
HETATM   24  O7  UNL     1       9.506  -0.452  -0.291  1.00  0.00           O  
HETATM   25  O8  UNL     1       3.347  -1.518   0.550  1.00  0.00           O  
HETATM   26  C18 UNL     1       1.982  -1.234   0.588  1.00  0.00           C  
HETATM   27  C19 UNL     1       1.852   0.266   0.666  1.00  0.00           C  
HETATM   28  O9  UNL     1       1.506   0.704   1.941  1.00  0.00           O  
HETATM   29  C20 UNL     1      -0.361   2.511   0.780  1.00  0.00           C  
HETATM   30  C21 UNL     1      -1.551   3.011   1.258  1.00  0.00           C  
HETATM   31  C22 UNL     1      -2.700   2.301   1.010  1.00  0.00           C  
HETATM   32  O10 UNL     1      -3.935   2.770   1.477  1.00  0.00           O  
HETATM   33  C23 UNL     1      -4.681  -1.823   0.353  1.00  0.00           C  
HETATM   34  O11 UNL     1      -3.740  -2.766   0.687  1.00  0.00           O  
HETATM   35  C24 UNL     1      -5.934  -2.412  -0.257  1.00  0.00           C  
HETATM   36  O12 UNL     1      -6.568  -3.267   0.623  1.00  0.00           O  
HETATM   37  C25 UNL     1      -6.877  -1.223  -0.467  1.00  0.00           C  
HETATM   38  O13 UNL     1      -8.138  -1.669  -0.842  1.00  0.00           O  
HETATM   39  H1  UNL     1      -5.274   1.826  -2.429  1.00  0.00           H  
HETATM   40  H2  UNL     1      -6.297   1.495  -0.350  1.00  0.00           H  
HETATM   41  H3  UNL     1      -7.753   1.082  -1.266  1.00  0.00           H  
HETATM   42  H4  UNL     1      -6.747  -0.664  -2.491  1.00  0.00           H  
HETATM   43  H5  UNL     1      -3.162  -1.132  -0.922  1.00  0.00           H  
HETATM   44  H6  UNL     1      -1.416  -0.265  -0.707  1.00  0.00           H  
HETATM   45  H7  UNL     1       0.806   0.101  -1.203  1.00  0.00           H  
HETATM   46  H8  UNL     1       3.424   2.750  -0.423  1.00  0.00           H  
HETATM   47  H9  UNL     1       3.579   1.532  -1.703  1.00  0.00           H  
HETATM   48  H10 UNL     1       4.610   1.874   1.014  1.00  0.00           H  
HETATM   49  H11 UNL     1       3.420  -0.672  -1.343  1.00  0.00           H  
HETATM   50  H12 UNL     1       5.364  -0.383  -2.521  1.00  0.00           H  
HETATM   51  H13 UNL     1       7.776  -0.339  -2.620  1.00  0.00           H  
HETATM   52  H14 UNL     1       5.579  -0.634   1.713  1.00  0.00           H  
HETATM   53  H15 UNL     1       9.788  -2.070   1.004  1.00  0.00           H  
HETATM   54  H16 UNL     1      10.572  -0.461   1.452  1.00  0.00           H  
HETATM   55  H17 UNL     1       1.532  -1.714   1.483  1.00  0.00           H  
HETATM   56  H18 UNL     1       1.498  -1.580  -0.348  1.00  0.00           H  
HETATM   57  H19 UNL     1       2.317   1.002   2.416  1.00  0.00           H  
HETATM   58  H20 UNL     1       0.547   3.092   0.987  1.00  0.00           H  
HETATM   59  H21 UNL     1      -1.589   3.954   1.823  1.00  0.00           H  
HETATM   60  H22 UNL     1      -4.790   2.293   1.326  1.00  0.00           H  
HETATM   61  H23 UNL     1      -5.014  -1.287   1.280  1.00  0.00           H  
HETATM   62  H24 UNL     1      -3.265  -2.447   1.513  1.00  0.00           H  
HETATM   63  H25 UNL     1      -5.764  -2.862  -1.245  1.00  0.00           H  
HETATM   64  H26 UNL     1      -6.228  -4.186   0.528  1.00  0.00           H  
HETATM   65  H27 UNL     1      -6.932  -0.691   0.502  1.00  0.00           H  
HETATM   66  H28 UNL     1      -8.792  -1.049  -0.423  1.00  0.00           H  
CONECT    1    2   39
CONECT    2    3   40   41
CONECT    3    4   37   42
CONECT    4    5
CONECT    5    6   33   43
CONECT    6    7
CONECT    7    8    8   31
CONECT    8    9   44
CONECT    9   10   29   29
CONECT   10   11   27   45
CONECT   11   12
CONECT   12   13   46   47
CONECT   13   14   15   27
CONECT   14   48
CONECT   15   16   25   49
CONECT   16   17   17   21
CONECT   17   18   50
CONECT   18   19   19   51
CONECT   19   20   24
CONECT   20   21   21   22
CONECT   21   52
CONECT   22   23
CONECT   23   24   53   54
CONECT   25   26
CONECT   26   27   55   56
CONECT   27   28
CONECT   28   57
CONECT   29   30   58
CONECT   30   31   31   59
CONECT   31   32
CONECT   32   60
CONECT   33   34   35   61
CONECT   34   62
CONECT   35   36   37   63
CONECT   36   64
CONECT   37   38   65
CONECT   38   66
END

NP0001535
     RDKit          3D

66 71  0  0  0  0  0  0  0  0999 V2000
   -6.2803    1.8907   -2.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6271    1.0639   -1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2344   -0.3593   -1.5281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9047   -0.5867   -1.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1391   -0.7436   -0.5696 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9182    0.4610    0.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7144    1.0945    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4888    0.6582   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3109    1.3313    0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0019    0.8538   -0.4100 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6698    1.9243   -0.9620 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0148    1.7608   -0.7729 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2443    0.7182    0.2656 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9721    1.1742    1.3601 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8257   -0.5390   -0.3264 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3038   -0.5133   -0.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414   -0.4298   -1.5868 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3189   -0.4062   -1.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1129   -0.4616   -0.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4661   -0.5449    0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0821   -0.5696    0.7709 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4783   -0.5864    1.6741 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6906   -0.9543    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5057   -0.4520   -0.2912 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3473   -1.5185    0.5505 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9823   -1.2339    0.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8519    0.2663    0.6657 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5060    0.7043    1.9405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605    2.5110    0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5511    3.0111    1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7003    2.3007    1.0105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9353    2.7702    1.4771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6810   -1.8226    0.3527 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7398   -2.7664    0.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9336   -2.4123   -0.2567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5675   -3.2669    0.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8775   -1.2233   -0.4670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.1378   -1.6689   -0.8416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2743    1.8263   -2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2974    1.4947   -0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7534    1.0820   -1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7468   -0.6639   -2.4911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1622   -1.1316   -0.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162   -0.2650   -0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057    0.1008   -1.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238    2.7498   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5787    1.5319   -1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6096    1.8742    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4199   -0.6717   -1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3643   -0.3827   -2.5206 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7760   -0.3389   -2.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5794   -0.6341    1.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7878   -2.0701    1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5721   -0.4609    1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -1.7138    1.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980   -1.5801   -0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3166    1.0018    2.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5469    3.0923    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5891    3.9543    1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7904    2.2932    1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0135   -1.2874    1.2804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -2.4467    1.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7645   -2.8624   -1.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2281   -4.1864    0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9321   -0.6913    0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7923   -1.0494   -0.4231 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
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  5 33  1  0
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  1 39  1  0
  2 40  1  0
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  3 42  1  6
  5 43  1  6
  8 44  1  0
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 37 65  1  1
 38 66  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₁₃

Average Mass

536.4860 Da

Monoisotopic Mass

536.15299 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{5-[(1R,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-hexahydrofuro[3,4-c]furan-1-yl]-2-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2S,3R,4S,5S,6R)-2-{5-[(1R,3aS,4R,6aS)-4-(2H-1,3-benzodioxol-5-yl)-3a,6a-dihydroxy-tetrahydrofuro[3,4-c]furan-1-yl]-2-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C([H])=C(C([H])=C1[H])[C@@]1([H])OC([H])([H])[C@]2(O[H])[C@]([H])(OC([H])([H])[C@]12O[H])C1=C([H])C2=C(OC([H])([H])O2)C([H])=C1[H]

InChI Identifier

InChI=1S/C25H28O13/c26-7-17-18(28)19(29)20(30)23(38-17)37-15-5-11(1-3-13(15)27)21-24(31)8-34-22(25(24,32)9-33-21)12-2-4-14-16(6-12)36-10-35-14/h1-6,17-23,26-32H,7-10H2/t17-,18-,19+,20-,21-,22-,23-,24+,25+/m1/s1

InChI Key

HUVQMIPFAVBQIA-KYBLTUFESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400Mz MHz, Methanol, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400Mz, Methanol, simulated)	rgf8b@missouri.edu	Not Available	Not Available	2020-08-26	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Vitex glabrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Furanoid lignan
Furofuran lignan skeleton
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzodioxole
Phenoxy compound
Furofuran
Phenol ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Monocyclic benzene moiety
Monosaccharide
Tertiary alcohol
Oxolane
Secondary alcohol
Polyol
Acetal
Dialkyl ether
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
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	-0.61	ALOGPS
logP	-1.4	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	196.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	122.26 m³·mol⁻¹	ChemAxon
Polarizability	51.78 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

24667364

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44606078

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for KHAINAOSIDE A (NP0001535)

MOL for NP0001535 (KHAINAOSIDE A)

3D MOL for NP0001535 (KHAINAOSIDE A)

3D SDF for NP0001535 (KHAINAOSIDE A)

3D-SDF for NP0001535 (KHAINAOSIDE A)

PDB for NP0001535 (KHAINAOSIDE A)

3D PDB for NP0001535 (KHAINAOSIDE A)

SMILES for NP0001535 (KHAINAOSIDE A)

INCHI for NP0001535 (KHAINAOSIDE A)

Structure for NP0001535 (KHAINAOSIDE A)

3D Structure for NP0001535 (KHAINAOSIDE A)