NP-MRD: Showing NP-Card for (-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+ (NP0028945)

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Record Information

Version

2.0

Created at

2021-06-19 20:41:54 UTC

Updated at

2021-06-29 23:56:01 UTC

NP-MRD ID

NP0028945

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+

Provided By

JEOL Database JEOL Logo

Description

(2S)-5,3'-Dihydroxy-4'-methoxy-6'',6''-dimethylpyrano[2'',3'':7,8]Flavanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. (-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+ is found in Feronia limonia. (-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+ was first documented in 2002 (Rahman, M. M., et al.). Based on a literature review very few articles have been published on (2S)-5,3'-Dihydroxy-4'-methoxy-6'',6''-dimethylpyrano[2'',3'':7,8]Flavanone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122413D          

 47 50  0  0  0  0            999 V2000
    0.2640    4.6511   -4.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    3.4511   -4.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8145    2.4537   -3.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6883   -2.3302    3.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785   -1.3053    2.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4361   -0.5206    0.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416   -0.0210    2.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400    0.1320    3.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398   -0.9571    4.9663 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7346   -0.4839    6.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -1.2678    5.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -2.2109    4.5078 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    0.1920   -3.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    1.2918   -4.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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    1.0013    3.4511   -4.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192122413D          

 47 50  0  0  0  0            999 V2000
    0.2640    4.6511   -4.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    3.4511   -4.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  2  0  0  0  0
 17 16  2  0  0  0  0
 21 22  1  1  0  0  0
 17 11  1  0  0  0  0
 21 23  1  0  0  0  0
  6  5  1  0  0  0  0
 12 13  1  0  0  0  0
 14 37  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  7 33  1  1  0  0  0
 25 46  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
 19 38  1  0  0  0  0
 20 39  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 27 47  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
 22 42  1  0  0  0  0
 23 43  1  0  0  0  0
 23 44  1  0  0  0  0
 23 45  1  0  0  0  0
 13 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028945

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C(=C1[H])[C@@]1([H])OC2=C3C([H])=C([H])C(OC3=C([H])C(O[H])=C2C(=O)C1([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O6/c1-21(2)7-6-12-18(27-21)10-15(24)19-14(23)9-17(26-20(12)19)11-4-5-16(25-3)13(22)8-11/h4-8,10,17,22,24H,9H2,1-3H3/t17-/m0/s1

> <INCHI_KEY>
IAYOSEMOKOQXBK-KRWDZBQOSA-N

> <FORMULA>
C21H20O6

> <MOLECULAR_WEIGHT>
368.385

> <EXACT_MASS>
368.125988364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
39.441748970069256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-8-hydroxy-4-(3-hydroxy-4-methoxyphenyl)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9,13-tetraen-6-one

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.8816255083333333

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.846065973863128

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.848747272941248

> <JCHEM_PKA_STRONGEST_BASIC>
-4.45257835617059

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
100.16550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-8-hydroxy-4-(3-hydroxy-4-methoxyphenyl)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9,13-tetraen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    0.2640    4.6511   -4.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    3.4511   -4.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8145    2.4537   -3.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0307    2.4996   -2.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209    1.3967   -2.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6353    0.2339   -2.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5277   -0.9746   -1.3237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6880   -1.8118   -1.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7330   -2.9887   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251   -4.0692   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132   -2.7893    0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952   -3.8026    1.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -5.0397    1.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -3.5755    2.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883   -2.3302    3.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785   -1.3053    2.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -1.5469    0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4361   -0.5206    0.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416   -0.0210    2.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400    0.1320    3.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398   -0.9571    4.9663 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7346   -0.4839    6.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -1.2678    5.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -2.2109    4.5078 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    0.1920   -3.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    1.2918   -4.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3968    1.2102   -5.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    4.4656   -4.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227    5.3429   -5.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387    5.1270   -3.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    3.3723   -2.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    1.4544   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4529   -1.5628   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254   -1.2562   -1.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155   -2.1740   -2.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1201   -5.0573    0.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0930   -4.3650    3.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    0.7809    1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    1.0857    4.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1072    0.4351    6.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846   -0.2983    5.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510   -1.2537    6.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958   -2.0517    6.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -1.6500    4.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -0.3842    5.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768   -0.6883   -3.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3073    2.0718   -5.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 26  1  0
 26  3  2  0
  3  4  1  0
  4  5  2  0
  7  6  1  0
 15 16  1  0
 17 18  1  0
 11  9  1  0
  9  8  1  0
  8  7  1  0
  7 18  1  0
  6 25  2  0
 15 24  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 24  1  0
  3  2  1  0
 15 14  2  0
  2  1  1  0
 14 12  1  0
 26 27  1  0
 12 11  2  0
  9 10  2  0
 17 16  2  0
 21 22  1  1
 17 11  1  0
 21 23  1  0
  6  5  1  0
 12 13  1  0
 14 37  1  0
  8 34  1  0
  8 35  1  0
  7 33  1  1
 25 46  1  0
  4 31  1  0
  5 32  1  0
 19 38  1  0
 20 39  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 47  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 23 45  1  0
 13 36  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.264   4.651  -4.691  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.001   3.451  -4.894  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.815   2.454  -3.973  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.031   2.500  -2.867  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.121   1.397  -2.006  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.635   0.234  -2.234  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.528  -0.975  -1.324  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.688  -1.812  -1.687  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.733  -2.989  -0.758  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.225  -4.069  -1.076  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.213  -2.789   0.609  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.295  -3.803   1.568  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.819  -5.040   1.307  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.159  -3.575   2.862  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.688  -2.330   3.209  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.779  -1.305   2.260  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.337  -1.547   0.946  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.436  -0.521   0.035  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.342  -0.021   2.660  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.740   0.132   3.925  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.640  -0.957   4.966  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.735  -0.484   6.110  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.039  -1.268   5.510  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.096  -2.211   4.508  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.479   0.192  -3.352  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.560   1.292  -4.199  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.397   1.210  -5.279  0.00  0.00           O+0
HETATM   28  H   UNK     0      -0.814   4.466  -4.743  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.523   5.343  -5.498  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.539   5.127  -3.743  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.634   3.372  -2.640  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.788   1.454  -1.148  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.453  -1.563  -1.415  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.625  -1.256  -1.569  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.616  -2.174  -2.718  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.120  -5.057   0.370  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.093  -4.365   3.606  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.428   0.781   1.935  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.160   1.086   4.235  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.107   0.435   6.575  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.285  -0.298   5.750  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.651  -1.254   6.886  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.996  -2.052   6.275  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.691  -1.650   4.715  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.515  -0.384   5.949  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.077  -0.688  -3.573  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.307   2.072  -5.731  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3   26    4    2                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6   32                                                  
CONECT    6    7   25    5                                                  
CONECT    7    6    8   18   33                                             
CONECT    8    9    7   34   35                                             
CONECT    9   11    8   10                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   14   11   13                                                  
CONECT   13   12   36                                                       
CONECT   14   15   12   37                                                  
CONECT   15   16   24   14                                                  
CONECT   16   15   19   17                                                  
CONECT   17   18   16   11                                                  
CONECT   18   17    7                                                       
CONECT   19   16   20   38                                                  
CONECT   20   19   21   39                                                  
CONECT   21   20   24   22   23                                             
CONECT   22   21   40   41   42                                             
CONECT   23   21   43   44   45                                             
CONECT   24   15   21                                                       
CONECT   25   26    6   46                                                  
CONECT   26   25    3   27                                                  
CONECT   27   26   47                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    7                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36   13                                                            
CONECT   37   14                                                            
CONECT   38   19                                                            
CONECT   39   20                                                            
CONECT   40   22                                                            
CONECT   41   22                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
CONECT   44   23                                                            
CONECT   45   23                                                            
CONECT   46   25                                                            
CONECT   47   27                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

RDKit          3D

47 50  0  0  0  0  0  0  0  0999 V2000
    0.2640    4.6511   -4.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    3.4511   -4.8945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8145    2.4537   -3.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0307    2.4996   -2.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1209    1.3967   -2.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6353    0.2339   -2.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5277   -0.9746   -1.3237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6880   -1.8118   -1.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7330   -2.9887   -0.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2251   -4.0692   -1.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132   -2.7893    0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952   -3.8026    1.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8185   -5.0397    1.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1588   -3.5755    2.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6883   -2.3302    3.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7785   -1.3053    2.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -1.5469    0.9461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4361   -0.5206    0.0354 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3416   -0.0210    2.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400    0.1320    3.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398   -0.9571    4.9663 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7346   -0.4839    6.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0393   -1.2678    5.5100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0959   -2.2109    4.5078 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788    0.1920   -3.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    1.2918   -4.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3968    1.2102   -5.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8138    4.4656   -4.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5227    5.3429   -5.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387    5.1270   -3.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    3.3723   -2.6403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    1.4544   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4529   -1.5628   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6254   -1.2562   -1.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6155   -2.1740   -2.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1201   -5.0573    0.3704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0930   -4.3650    3.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    0.7809    1.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1600    1.0857    4.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1072    0.4351    6.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846   -0.2983    5.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6510   -1.2537    6.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9958   -2.0517    6.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909   -1.6500    4.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -0.3842    5.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768   -0.6883   -3.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3073    2.0718   -5.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 26  1  0
 26  3  2  0
  3  4  1  0
  4  5  2  0
  7  6  1  0
 15 16  1  0
 17 18  1  0
 11  9  1  0
  9  8  1  0
  8  7  1  0
  7 18  1  0
  6 25  2  0
 15 24  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 24  1  0
  3  2  1  0
 15 14  2  0
  2  1  1  0
 14 12  1  0
 26 27  1  0
 12 11  2  0
  9 10  2  0
 17 16  2  0
 21 22  1  1
 17 11  1  0
 21 23  1  0
  6  5  1  0
 12 13  1  0
 14 37  1  0
  8 34  1  0
  8 35  1  0
  7 33  1  1
 25 46  1  0
  4 31  1  0
  5 32  1  0
 19 38  1  0
 20 39  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 47  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 23 45  1  0
 13 36  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₀O₆

Average Mass

368.3850 Da

Monoisotopic Mass

368.12599 Da

IUPAC Name

(4S)-8-hydroxy-4-(3-hydroxy-4-methoxyphenyl)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9,13-tetraen-6-one

Traditional Name

(4S)-8-hydroxy-4-(3-hydroxy-4-methoxyphenyl)-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,7,9,13-tetraen-6-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C([H])C(=C1[H])[C@@]1([H])OC2=C3C([H])=C([H])C(OC3=C([H])C(O[H])=C2C(=O)C1([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H20O6/c1-21(2)7-6-12-18(27-21)10-15(24)19-14(23)9-17(26-20(12)19)11-4-5-16(25-3)13(22)8-11/h4-8,10,17,22,24H,9H2,1-3H3/t17-/m0/s1

InChI Key

IAYOSEMOKOQXBK-KRWDZBQOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Limonia acidissima	JEOL database	Rahman, M. M., et al, Phytochemistry 59, 73 (2002)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
3'-hydroxyflavonoid
5-hydroxyflavonoid
Flavanone
Flavan
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
Chromane
Methoxyphenol
1-benzopyran
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Anisole
Phenoxy compound
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140385 )

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	3.58	ALOGPS
logP	3.88	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.85	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.17 m³·mol⁻¹	ChemAxon
Polarizability	39.44 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

552292

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636525

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rahman, M. M., et al. (2002). Rahman, M. M., et al, Phytochemistry 59, 73 (2002). Phytochem..

Showing NP-Card for (-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+ (NP0028945)

MOL for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

3D MOL for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

3D SDF for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

3D-SDF for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

PDB for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

3D PDB for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

SMILES for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

INCHI for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

Structure for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)

3D Structure for NP0028945 ((-)-(2S)-5,3'-dihydroxy-4'-methoxy-6'',6''-dimethylchromeno-(7,8,2'',3'')+)