NP-MRD: Showing NP-Card for Jacein (NP0043912)

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Record Information

Version

1.0

Created at

2021-06-22 17:28:48 UTC

Updated at

2021-06-22 17:28:48 UTC

NP-MRD ID

NP0043912

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Jacein

Description

Jacein belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Jacein is found in Bidens pilosa, Centaurea bracteata, Centaurea nigra and Tridax procumbens. It was first documented in 2004 (PMID: 15507368). Based on a literature review very few articles have been published on Jacein (PMID: 27719955) (PMID: 34567171).

Structure

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


  Mrv1652306222119282D          

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M  END

NP0043912
     RDKit          3D

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M  END


  Mrv1652306222119282D          

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M  END
> <DATABASE_ID>
NP0043912

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(O[C@@H]3OC(CO)[C@@H](O)[C@H](O)C3O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O13/c1-32-11-6-9(4-5-10(11)26)21-23(34-3)18(29)15-12(35-21)7-13(22(33-2)17(15)28)36-24-20(31)19(30)16(27)14(8-25)37-24/h4-7,14,16,19-20,24-28,30-31H,8H2,1-3H3/t14?,16-,19+,20?,24-/m1/s1

> <INCHI_KEY>
NYTZRFVFIRTFIX-NIZXRZDQSA-N

> <FORMULA>
C24H26O13

> <MOLECULAR_WEIGHT>
522.459

> <EXACT_MASS>
522.137340897

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
50.88610558916618

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6-dimethoxy-7-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
-0.010718449666666519

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.04695689371531

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.6667569848292185

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354981798

> <JCHEM_POLAR_SURFACE_AREA>
193.82999999999998

> <JCHEM_REFRACTIVITY>
124.70329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
jacein

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043912
     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
    8.3119   -0.6882    0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1517   -0.3252   -0.3709 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9138   -0.0629   -0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7642   -0.1496   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    0.0991   -0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    0.0857    0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    0.1202   -0.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537    0.1108    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2156    0.1467   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957    0.1365    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5839    0.1799   -0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9326    0.2363   -0.6356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4678   -0.9161   -1.2510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8007   -1.0942   -1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1546   -1.7720    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5482   -3.0396    0.2217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5705    0.1922   -1.2631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8406    0.8577   -0.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6898    1.1226   -2.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3693    0.5533   -3.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5072    1.5122   -1.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5245    2.1623   -2.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740    0.0863    1.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706    0.0603    2.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3147   -1.2091    2.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905    0.0516    2.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    0.0060    3.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549    0.0638    1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0215    0.0285    2.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9533   -0.0147    3.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677    0.0405    1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3744    0.0115    2.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8199    1.3099    2.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    0.4492   -1.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5560    0.5389   -2.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104    0.2814   -2.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9408    0.3750   -3.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6015   -1.5409    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0039    0.1597    1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3440   -0.9968    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8908   -0.4556    0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767    0.1849   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3475    0.2439    0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1843   -1.7842   -1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8409   -1.2618    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2641   -1.9688    0.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6931   -2.9623   -0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4959    0.0343   -1.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1869    0.2805    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3178    2.0331   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4882    0.1126   -3.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8421    2.2165   -0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    1.7321   -1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2594   -0.9881    3.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6608   -1.7692    3.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5446   -1.7772    1.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3293    0.0129    3.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6243    2.0667    2.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1770    1.5250    3.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    1.2689    3.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    0.6534   -2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4955    0.8082   -3.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8765    0.6256   -4.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  2  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
  5 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36  3  1  0
 31  6  2  0
 28  8  1  0
 21 12  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  9 42  1  0
 12 43  1  1
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  6
 18 49  1  0
 19 50  1  6
 20 51  1  0
 21 52  1  0
 22 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 27 57  1  0
 33 58  1  0
 33 59  1  0
 33 60  1  0
 34 61  1  0
 35 62  1  0
 37 63  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   37                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   19                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   34                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9                                                       
CONECT   20   16   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
CONECT   31   22                                                            
CONECT   32   15   33                                                       
CONECT   33   32                                                            
CONECT   34   14                                                            
CONECT   35   10   36                                                       
CONECT   36   35                                                            
CONECT   37    4                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

COMPND    NP0043912
HETATM    1  C1  UNL     1       8.312  -0.688   1.000  1.00  0.00           C  
HETATM    2  O1  UNL     1       8.152  -0.325  -0.371  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.914  -0.063  -0.904  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.764  -0.150  -0.094  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.522   0.099  -0.566  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.285   0.086   0.181  1.00  0.00           C  
HETATM    7  O2  UNL     1       2.121   0.120  -0.481  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.954   0.111   0.114  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.216   0.147  -0.593  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.496   0.137   0.016  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.584   0.180  -0.769  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.933   0.236  -0.636  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.468  -0.916  -1.251  1.00  0.00           O  
HETATM   14  C10 UNL     1      -5.801  -1.094  -1.049  1.00  0.00           C  
HETATM   15  C11 UNL     1      -6.155  -1.772   0.232  1.00  0.00           C  
HETATM   16  O5  UNL     1      -5.548  -3.040   0.222  1.00  0.00           O  
HETATM   17  C12 UNL     1      -6.571   0.192  -1.263  1.00  0.00           C  
HETATM   18  O6  UNL     1      -6.841   0.858  -0.092  1.00  0.00           O  
HETATM   19  C13 UNL     1      -5.690   1.123  -2.112  1.00  0.00           C  
HETATM   20  O7  UNL     1      -5.369   0.553  -3.322  1.00  0.00           O  
HETATM   21  C14 UNL     1      -4.507   1.512  -1.279  1.00  0.00           C  
HETATM   22  O8  UNL     1      -3.525   2.162  -2.016  1.00  0.00           O  
HETATM   23  C15 UNL     1      -1.574   0.086   1.380  1.00  0.00           C  
HETATM   24  O9  UNL     1      -2.771   0.060   2.103  1.00  0.00           O  
HETATM   25  C16 UNL     1      -3.315  -1.209   2.514  1.00  0.00           C  
HETATM   26  C17 UNL     1      -0.391   0.052   2.110  1.00  0.00           C  
HETATM   27  O10 UNL     1      -0.432   0.006   3.497  1.00  0.00           O  
HETATM   28  C18 UNL     1       0.855   0.064   1.484  1.00  0.00           C  
HETATM   29  C19 UNL     1       2.022   0.029   2.199  1.00  0.00           C  
HETATM   30  O11 UNL     1       1.953  -0.015   3.453  1.00  0.00           O  
HETATM   31  C20 UNL     1       3.268   0.041   1.543  1.00  0.00           C  
HETATM   32  O12 UNL     1       4.374   0.012   2.372  1.00  0.00           O  
HETATM   33  C21 UNL     1       4.820   1.310   2.814  1.00  0.00           C  
HETATM   34  C22 UNL     1       4.447   0.449  -1.923  1.00  0.00           C  
HETATM   35  C23 UNL     1       5.556   0.539  -2.732  1.00  0.00           C  
HETATM   36  C24 UNL     1       6.810   0.281  -2.224  1.00  0.00           C  
HETATM   37  O13 UNL     1       7.941   0.375  -3.054  1.00  0.00           O  
HETATM   38  H1  UNL     1       7.602  -1.541   1.171  1.00  0.00           H  
HETATM   39  H2  UNL     1       8.004   0.160   1.643  1.00  0.00           H  
HETATM   40  H3  UNL     1       9.344  -0.997   1.220  1.00  0.00           H  
HETATM   41  H4  UNL     1       5.891  -0.456   0.937  1.00  0.00           H  
HETATM   42  H5  UNL     1      -0.177   0.185  -1.669  1.00  0.00           H  
HETATM   43  H6  UNL     1      -4.348   0.244   0.388  1.00  0.00           H  
HETATM   44  H7  UNL     1      -6.184  -1.784  -1.869  1.00  0.00           H  
HETATM   45  H8  UNL     1      -5.841  -1.262   1.141  1.00  0.00           H  
HETATM   46  H9  UNL     1      -7.264  -1.969   0.236  1.00  0.00           H  
HETATM   47  H10 UNL     1      -4.693  -2.962  -0.279  1.00  0.00           H  
HETATM   48  H11 UNL     1      -7.496   0.034  -1.840  1.00  0.00           H  
HETATM   49  H12 UNL     1      -7.187   0.280   0.635  1.00  0.00           H  
HETATM   50  H13 UNL     1      -6.318   2.033  -2.275  1.00  0.00           H  
HETATM   51  H14 UNL     1      -4.488   0.113  -3.351  1.00  0.00           H  
HETATM   52  H15 UNL     1      -4.842   2.216  -0.499  1.00  0.00           H  
HETATM   53  H16 UNL     1      -2.626   1.732  -1.924  1.00  0.00           H  
HETATM   54  H17 UNL     1      -4.259  -0.988   3.048  1.00  0.00           H  
HETATM   55  H18 UNL     1      -2.661  -1.769   3.177  1.00  0.00           H  
HETATM   56  H19 UNL     1      -3.545  -1.777   1.581  1.00  0.00           H  
HETATM   57  H20 UNL     1      -1.329   0.013   3.948  1.00  0.00           H  
HETATM   58  H21 UNL     1       4.624   2.067   2.043  1.00  0.00           H  
HETATM   59  H22 UNL     1       4.177   1.525   3.710  1.00  0.00           H  
HETATM   60  H23 UNL     1       5.882   1.269   3.092  1.00  0.00           H  
HETATM   61  H24 UNL     1       3.476   0.653  -2.333  1.00  0.00           H  
HETATM   62  H25 UNL     1       5.495   0.808  -3.774  1.00  0.00           H  
HETATM   63  H26 UNL     1       7.876   0.626  -4.019  1.00  0.00           H  
CONECT    1    2   38   39   40
CONECT    2    3
CONECT    3    4    4   36
CONECT    4    5   41
CONECT    5    6   34   34
CONECT    6    7   31   31
CONECT    7    8
CONECT    8    9    9   28
CONECT    9   10   42
CONECT   10   11   23   23
CONECT   11   12
CONECT   12   13   21   43
CONECT   13   14
CONECT   14   15   17   44
CONECT   15   16   45   46
CONECT   16   47
CONECT   17   18   19   48
CONECT   18   49
CONECT   19   20   21   50
CONECT   20   51
CONECT   21   22   52
CONECT   22   53
CONECT   23   24   26
CONECT   24   25
CONECT   25   54   55   56
CONECT   26   27   28   28
CONECT   27   57
CONECT   28   29
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   33
CONECT   33   58   59   60
CONECT   34   35   61
CONECT   35   36   36   62
CONECT   36   37
CONECT   37   63
END

NP0043912
     RDKit          3D

63 66  0  0  0  0  0  0  0  0999 V2000
    8.3119   -0.6882    0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1517   -0.3252   -0.3709 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9138   -0.0629   -0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7642   -0.1496   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217    0.0991   -0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2846    0.0857    0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1214    0.1202   -0.4807 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537    0.1108    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2156    0.1467   -0.5929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4957    0.1365    0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5839    0.1799   -0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9326    0.2363   -0.6356 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4678   -0.9161   -1.2510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8007   -1.0942   -1.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1546   -1.7720    0.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5482   -3.0396    0.2217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5705    0.1922   -1.2631 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8406    0.8577   -0.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6898    1.1226   -2.1119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3693    0.5533   -3.3215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5072    1.5122   -1.2792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5245    2.1623   -2.0162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5740    0.0863    1.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706    0.0603    2.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3147   -1.2091    2.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905    0.0516    2.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    0.0060    3.4970 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8549    0.0638    1.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0215    0.0285    2.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9533   -0.0147    3.4535 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677    0.0405    1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3744    0.0115    2.3723 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8199    1.3099    2.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    0.4492   -1.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5560    0.5389   -2.7322 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8104    0.2814   -2.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9408    0.3750   -3.0542 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6015   -1.5409    1.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0039    0.1597    1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3440   -0.9968    1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8908   -0.4556    0.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767    0.1849   -1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3475    0.2439    0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1843   -1.7842   -1.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8409   -1.2618    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2641   -1.9688    0.2363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6931   -2.9623   -0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4959    0.0343   -1.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1869    0.2805    0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3178    2.0331   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4882    0.1126   -3.3513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8421    2.2165   -0.4990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    1.7321   -1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2594   -0.9881    3.0484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6608   -1.7692    3.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5446   -1.7772    1.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3293    0.0129    3.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6243    2.0667    2.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1770    1.5250    3.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    1.2689    3.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    0.6534   -2.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4955    0.8082   -3.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8765    0.6256   -4.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  2  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
  5 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36  3  1  0
 31  6  2  0
 28  8  1  0
 21 12  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  9 42  1  0
 12 43  1  1
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 17 48  1  6
 18 49  1  0
 19 50  1  6
 20 51  1  0
 21 52  1  0
 22 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 27 57  1  0
 33 58  1  0
 33 59  1  0
 33 60  1  0
 34 61  1  0
 35 62  1  0
 37 63  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆O₁₃

Average Mass

522.4590 Da

Monoisotopic Mass

522.13734 Da

IUPAC Name

5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,6-dimethoxy-7-{[(2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

jacein

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(O[C@@H]3OC(CO)[C@@H](O)[C@H](O)C3O)C=C2O1

InChI Identifier

InChI=1S/C24H26O13/c1-32-11-6-9(4-5-10(11)26)21-23(34-3)18(29)15-12(35-21)7-13(22(33-2)17(15)28)36-24-20(31)19(30)16(27)14(8-25)37-24/h4-7,14,16,19-20,24-28,30-31H,8H2,1-3H3/t14?,16-,19+,20?,24-/m1/s1

InChI Key

NYTZRFVFIRTFIX-NIZXRZDQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, 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
Bidens pilosa	LOTUS Database	35616633
Centaurea bracteata	LOTUS Database	35616633
Centaurea bracteata Scop.	KNApSAcK Database	22123792
Centaurea hyssopifolia	KNApSAcK Database	22123792
Centaurea jacea	KNApSAcK Database	22123792
Centaurea nigra	LOTUS Database	35616633
Desmanthodium spp.	KNApSAcK Database	22123792
Tetragonotheca ludoviciana	KNApSAcK Database	22123792
Tridax procumbens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3p-methoxyflavonoid-skeleton
3-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
4'-hydroxyflavonoid
5-hydroxyflavonoid
Phenolic glycoside
3-methoxychromone
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Phenol
Pyranone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyran
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Acetal
Polyol
Ether
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic oxide
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12112929 )

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	0.76	ALOGPS
logP	-0.011	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	193.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	124.7 m³·mol⁻¹	ChemAxon
Polarizability	50.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00005671

Chemspider ID

24845526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44259819

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Blunder M, Orthaber A, Bauer R, Bucar F, Kunert O: Efficient identification of flavones, flavanones and their glycosides in routine analysis via off-line combination of sensitive NMR and HPLC experiments. Food Chem. 2017 Mar 1;218:600-609. doi: 10.1016/j.foodchem.2016.09.077. Epub 2016 Sep 13. [PubMed:27719955 ]
Chiang YM, Chuang DY, Wang SY, Kuo YH, Tsai PW, Shyur LF: Metabolite profiling and chemopreventive bioactivity of plant extracts from Bidens pilosa. J Ethnopharmacol. 2004 Dec;95(2-3):409-19. doi: 10.1016/j.jep.2004.08.010. [PubMed:15507368 ]
Aghaei M, Mirzaei M, Ghanadian M, Fallah M, Mahboodi R: 6-Methoxylated Flavonoids: Jacein, and 3-demethyljacein from Centaurea schmidii with Their Endoplasmic Reticulum Stress and Apoptotic Cell Death in Breast Cancer Cells Along with In-silico Analysis. Iran J Pharm Res. 2021 Spring;20(2):417-432. doi: 10.22037/ijpr.2020.113895.14548. [PubMed:34567171 ]

Showing NP-Card for Jacein (NP0043912)

MOL for NP0043912 (Jacein)

3D MOL for NP0043912 (Jacein)

3D SDF for NP0043912 (Jacein)

3D-SDF for NP0043912 (Jacein)

PDB for NP0043912 (Jacein)

3D PDB for NP0043912 (Jacein)

SMILES for NP0043912 (Jacein)

INCHI for NP0043912 (Jacein)

Structure for NP0043912 (Jacein)

3D Structure for NP0043912 (Jacein)