NP-MRD: Showing NP-Card for aciculatinone (NP0036497)

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Record Information

Version

2.0

Created at

2021-06-20 19:39:19 UTC

Updated at

2021-06-30 00:08:10 UTC

NP-MRD ID

NP0036497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

aciculatinone

Provided By

JEOL Database JEOL Logo

Description

ACICULATINONE belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. aciculatinone is found in Chrysopogon aciculatis. aciculatinone was first documented in 2012 (PMID: 22272829). Based on a literature review very few articles have been published on ACICULATINONE.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121393D          

 50 53  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306202121393D          

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 12 13  2  0  0  0  0
 21  3  1  0  0  0  0
 13 14  1  0  0  0  0
 20 19  1  0  0  0  0
 14 15  2  0  0  0  0
  7  8  1  0  0  0  0
 15 17  1  0  0  0  0
  8 10  1  0  0  0  0
 17 18  2  0  0  0  0
 18 12  1  0  0  0  0
 22 30  1  0  0  0  0
 10 11  2  0  0  0  0
 11 19  1  0  0  0  0
 20  7  1  0  0  0  0
  8  9  2  0  0  0  0
 22 23  1  0  0  0  0
 30 28  1  0  0  0  0
 28 26  1  0  0  0  0
 26 24  1  0  0  0  0
 24 23  1  0  0  0  0
  5  6  1  0  0  0  0
 28 29  1  0  0  0  0
  4  5  1  0  0  0  0
 24 25  2  0  0  0  0
  3  2  1  0  0  0  0
 26 27  1  0  0  0  0
  5  7  2  0  0  0  0
 15 16  1  0  0  0  0
  2  1  1  0  0  0  0
 22 21  1  0  0  0  0
  4 34  1  0  0  0  0
 10 36  1  0  0  0  0
  6 35  1  0  0  0  0
 22 42  1  1  0  0  0
 13 37  1  0  0  0  0
 14 38  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 28 47  1  1  0  0  0
 26 45  1  6  0  0  0
 23 43  1  0  0  0  0
 23 44  1  0  0  0  0
 29 48  1  0  0  0  0
 29 49  1  0  0  0  0
 29 50  1  0  0  0  0
 27 46  1  0  0  0  0
 16 39  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0036497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[H])C([H])=C(OC([H])([H])[H])C(=C2O1)[C@]1([H])O[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C(=O)C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O8/c1-10-21(27)15(26)9-18(29-10)20-17(28-2)8-14(25)19-13(24)7-16(30-22(19)20)11-3-5-12(23)6-4-11/h3-8,10,18,21,23,25,27H,9H2,1-2H3/t10-,18-,21-/m1/s1

> <INCHI_KEY>
CFHMTDWOLGJZEJ-LMCQJGHKSA-N

> <FORMULA>
C22H20O8

> <MOLECULAR_WEIGHT>
412.394

> <EXACT_MASS>
412.115817604

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.72693901452656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-8-[(2R,5R,6R)-5-hydroxy-6-methyl-4-oxooxan-2-yl]-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
2.472506886333333

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.740637484176192

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.292214291944699

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9211077085708395

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
106.86590000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aciculatinone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -2.1290   -1.3425    4.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799   -1.3510    3.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6587   -1.4192    2.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155   -1.5423    2.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165   -1.6370    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616   -1.7566    0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -1.6192   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8685   -1.7367   -1.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477   -1.8453   -2.0538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8002   -1.7226   -2.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5313   -1.6170   -2.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5982   -1.5800   -3.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -2.4800   -4.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -2.4350   -5.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873   -1.4952   -5.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8329   -1.4890   -5.8895 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7213   -0.5971   -3.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6285   -0.6437   -3.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -1.5065   -1.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147   -1.4971   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867   -1.3771    1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7892   -1.2422    1.6738 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5174   -2.5722    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774   -2.3441    1.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -3.1158    2.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6313   -1.1740    1.0635 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9393   -0.9284    1.5665 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    0.0558    1.2476 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2303    1.2313    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -0.2342    0.8419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5761   -1.2570    5.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7962   -0.4774    4.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6935   -2.2801    4.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -1.5738    2.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9066   -1.8145   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976   -1.7873   -3.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743   -3.2344   -4.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8522   -3.1346   -6.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4477   -0.7808   -5.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002    0.1406   -3.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5795    0.0651   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -0.8894    2.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441   -2.9706    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239   -3.3221    2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.4555    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -1.7922    1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    0.3761    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5509    2.0842    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2333    1.5479    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505    0.9745   -0.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 11 12  1  0
 20 21  2  0
 12 13  2  0
 21  3  1  0
 13 14  1  0
 20 19  1  0
 14 15  2  0
  7  8  1  0
 15 17  1  0
  8 10  1  0
 17 18  2  0
 18 12  1  0
 22 30  1  0
 10 11  2  0
 11 19  1  0
 20  7  1  0
  8  9  2  0
 22 23  1  0
 30 28  1  0
 28 26  1  0
 26 24  1  0
 24 23  1  0
  5  6  1  0
 28 29  1  0
  4  5  1  0
 24 25  2  0
  3  2  1  0
 26 27  1  0
  5  7  2  0
 15 16  1  0
  2  1  1  0
 22 21  1  0
  4 34  1  0
 10 36  1  0
  6 35  1  0
 22 42  1  1
 13 37  1  0
 14 38  1  0
 17 40  1  0
 18 41  1  0
 28 47  1  1
 26 45  1  6
 23 43  1  0
 23 44  1  0
 29 48  1  0
 29 49  1  0
 29 50  1  0
 27 46  1  0
 16 39  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.129  -1.343   4.694  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.180  -1.351   3.633  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.659  -1.419   2.349  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.015  -1.542   2.027  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.417  -1.637   0.697  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.762  -1.757   0.470  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.470  -1.619  -0.326  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.869  -1.737  -1.735  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.048  -1.845  -2.054  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.800  -1.723  -2.741  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.531  -1.617  -2.326  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.598  -1.580  -3.272  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.692  -2.480  -4.344  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.784  -2.435  -5.215  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.787  -1.495  -5.016  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.833  -1.489  -5.890  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.721  -0.597  -3.957  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.629  -0.644  -3.087  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.152  -1.506  -1.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.115  -1.497  -0.018  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.687  -1.377   1.323  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.789  -1.242   1.674  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.517  -2.572   1.512  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.977  -2.344   1.789  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.642  -3.116   2.484  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.631  -1.174   1.063  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.939  -0.928   1.567  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.738   0.056   1.248  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.230   1.231   0.410  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.392  -0.234   0.842  0.00  0.00           O+0
HETATM   31  H   UNK     0      -1.576  -1.257   5.634  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.796  -0.477   4.620  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.693  -2.280   4.724  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.789  -1.574   2.788  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.907  -1.815  -0.502  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.098  -1.787  -3.779  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.074  -3.234  -4.508  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.852  -3.135  -6.043  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.448  -0.781  -5.636  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.500   0.141  -3.792  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.579   0.065  -2.262  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.895  -0.889   2.707  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.444  -2.971   0.494  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.124  -3.322   2.206  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.709  -1.456   0.007  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.277  -1.792   1.881  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.736   0.376   2.298  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.551   2.084   0.515  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.233   1.548   0.711  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.251   0.975  -0.654  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    3    1                                                       
CONECT    3    4   21    2                                                  
CONECT    4    3    5   34                                                  
CONECT    5    6    4    7                                                  
CONECT    6    5   35                                                       
CONECT    7    8   20    5                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11   36                                                  
CONECT   11   12   10   19                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   37                                                  
CONECT   14   13   15   38                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15   39                                                       
CONECT   17   15   18   40                                                  
CONECT   18   17   12   41                                                  
CONECT   19   20   11                                                       
CONECT   20   21   19    7                                                  
CONECT   21   20    3   22                                                  
CONECT   22   30   23   21   42                                             
CONECT   23   22   24   43   44                                             
CONECT   24   26   23   25                                                  
CONECT   25   24                                                            
CONECT   26   28   24   27   45                                             
CONECT   27   26   46                                                       
CONECT   28   30   26   29   47                                             
CONECT   29   28   48   49   50                                             
CONECT   30   22   28                                                       
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36   10                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
CONECT   44   23                                                            
CONECT   45   26                                                            
CONECT   46   27                                                            
CONECT   47   28                                                            
CONECT   48   29                                                            
CONECT   49   29                                                            
CONECT   50   29                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  106    0
END

RDKit          3D

50 53  0  0  0  0  0  0  0  0999 V2000
   -2.1290   -1.3425    4.6937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1799   -1.3510    3.6328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6587   -1.4192    2.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0155   -1.5423    2.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165   -1.6370    0.6974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616   -1.7566    0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4697   -1.6192   -0.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8685   -1.7367   -1.7346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477   -1.8453   -2.0538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8002   -1.7226   -2.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5313   -1.6170   -2.3256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5982   -1.5800   -3.2721 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6916   -2.4800   -4.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7837   -2.4350   -5.2145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7873   -1.4952   -5.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8329   -1.4890   -5.8895 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7213   -0.5971   -3.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6285   -0.6437   -3.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -1.5065   -1.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1147   -1.4971   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6867   -1.3771    1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7892   -1.2422    1.6738 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5174   -2.5722    1.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774   -2.3441    1.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -3.1158    2.4837 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6313   -1.1740    1.0635 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9393   -0.9284    1.5665 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    0.0558    1.2476 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2303    1.2313    0.4100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -0.2342    0.8419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5761   -1.2570    5.6341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7962   -0.4774    4.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6935   -2.2801    4.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7890   -1.5738    2.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9066   -1.8145   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0976   -1.7873   -3.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0743   -3.2344   -4.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8522   -3.1346   -6.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4477   -0.7808   -5.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5002    0.1406   -3.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5795    0.0651   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948   -0.8894    2.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4441   -2.9706    0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239   -3.3221    2.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7092   -1.4555    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -1.7922    1.8812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7355    0.3761    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5509    2.0842    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2333    1.5479    0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2505    0.9745   -0.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 11 12  1  0
 20 21  2  0
 12 13  2  0
 21  3  1  0
 13 14  1  0
 20 19  1  0
 14 15  2  0
  7  8  1  0
 15 17  1  0
  8 10  1  0
 17 18  2  0
 18 12  1  0
 22 30  1  0
 10 11  2  0
 11 19  1  0
 20  7  1  0
  8  9  2  0
 22 23  1  0
 30 28  1  0
 28 26  1  0
 26 24  1  0
 24 23  1  0
  5  6  1  0
 28 29  1  0
  4  5  1  0
 24 25  2  0
  3  2  1  0
 26 27  1  0
  5  7  2  0
 15 16  1  0
  2  1  1  0
 22 21  1  0
  4 34  1  0
 10 36  1  0
  6 35  1  0
 22 42  1  1
 13 37  1  0
 14 38  1  0
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 28 47  1  1
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 23 44  1  0
 29 48  1  0
 29 49  1  0
 29 50  1  0
 27 46  1  0
 16 39  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₈

Average Mass

412.3940 Da

Monoisotopic Mass

412.11582 Da

IUPAC Name

5-hydroxy-8-[(2R,5R,6R)-5-hydroxy-6-methyl-4-oxooxan-2-yl]-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

Traditional Name

aciculatinone

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(=O)C2=C(O[H])C([H])=C(OC([H])([H])[H])C(=C2O1)[C@]1([H])O[C@]([H])(C([H])([H])[H])[C@@]([H])(O[H])C(=O)C1([H])[H]

InChI Identifier

InChI=1S/C22H20O8/c1-10-21(27)15(26)9-18(29-10)20-17(28-2)8-14(25)19-13(24)7-16(30-22(19)20)11-3-5-12(23)6-4-11/h3-8,10,18,21,23,25,27H,9H2,1-2H3/t10-,18-,21-/m1/s1

InChI Key

CFHMTDWOLGJZEJ-LMCQJGHKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-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
Chrysopogon aciculatis	JEOL database	Shen, C. -C., et al, J. Nat. Prod. 75, 198 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Oxane
Pyran
Vinylogous acid
Heteroaromatic compound
Ketone
Cyclic ketone
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.76	ALOGPS
logP	2.47	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.29	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.87 m³·mol⁻¹	ChemAxon
Polarizability	41.73 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

Not Available

Chemspider ID

28501395

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57332647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shen CC, Cheng JJ, Lay HL, Wu SY, Ni CL, Teng CM, Chen CC: Cytotoxic apigenin derivatives from Chrysopogon aciculatis. J Nat Prod. 2012 Feb 24;75(2):198-201. doi: 10.1021/np2007796. Epub 2012 Jan 24. [PubMed:22272829 ]
Shen, C. -C., et al. (2012). Shen, C. -C., et al, J. Nat. Prod. 75, 198 (2012). J. Nat. Prod..

Showing NP-Card for aciculatinone (NP0036497)

MOL for NP0036497 (aciculatinone)

3D MOL for NP0036497 (aciculatinone)

3D SDF for NP0036497 (aciculatinone)

3D-SDF for NP0036497 (aciculatinone)

PDB for NP0036497 (aciculatinone)

3D PDB for NP0036497 (aciculatinone)

SMILES for NP0036497 (aciculatinone)

INCHI for NP0036497 (aciculatinone)

Structure for NP0036497 (aciculatinone)

3D Structure for NP0036497 (aciculatinone)