NP-MRD: Showing NP-Card for 5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+ (NP0028018)

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Record Information

Version

2.0

Created at

2021-06-19 20:01:17 UTC

Updated at

2021-06-29 23:54:32 UTC

NP-MRD ID

NP0028018

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+

Provided By

JEOL Database JEOL Logo

Description

5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+ is found in Marila pluricostata. 5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+ was first documented in 2005 (Lopez-Perez, J. L., et al.). Based on a literature review very few articles have been published on 8-hydroxy-12,12-dimethyl-6-phenyl-9-propanoyl-3,11-dioxatricyclo[8.4.0.0²,⁷]Tetradeca-1,5,7,9-tetraen-4-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122013D          

 50 53  0  0  0  0            999 V2000
    1.9356    1.2545    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249    1.7257    2.2104 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.1739    1.1843    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9102   -1.1974   -2.8822 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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M  END


  Mrv1652306192122013D          

 50 53  0  0  0  0            999 V2000
    1.9356    1.2545    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249    1.7257    2.2104 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.8433    5.3767   -0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405    4.7089    0.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7106    4.8678   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9590    3.3609   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  8  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
 13 14  1  0  0  0  0
  7  6  1  0  0  0  0
 20 13  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 23  1  0  0  0  0
  6 28  1  0  0  0  0
 28 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24 23  1  0  0  0  0
  5  6  2  0  0  0  0
 25 26  1  0  0  0  0
 14 15  2  0  0  0  0
 25 27  1  0  0  0  0
  5 21  1  0  0  0  0
 10 11  2  0  0  0  0
 15 16  1  0  0  0  0
 21 22  1  0  0  0  0
  7  8  2  0  0  0  0
  5  3  1  0  0  0  0
 16 17  2  0  0  0  0
  3  4  2  0  0  0  0
 20 21  2  0  0  0  0
  3  2  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  1  0  0  0  0
 12 34  1  0  0  0  0
 15 35  1  0  0  0  0
 16 36  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  0  0  0  0
 19 39  1  0  0  0  0
 24 43  1  0  0  0  0
 24 44  1  0  0  0  0
 23 41  1  0  0  0  0
 23 42  1  0  0  0  0
 26 45  1  0  0  0  0
 26 46  1  0  0  0  0
 26 47  1  0  0  0  0
 27 48  1  0  0  0  0
 27 49  1  0  0  0  0
 27 50  1  0  0  0  0
 22 40  1  0  0  0  0
  2 32  1  0  0  0  0
  2 33  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028018

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(OC(=O)C([H])=C2C2=C([H])C([H])=C([H])C([H])=C2[H])=C2C(OC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C2([H])[H])=C1C(=O)C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O5/c1-4-16(24)19-20(26)18-15(13-8-6-5-7-9-13)12-17(25)27-21(18)14-10-11-23(2,3)28-22(14)19/h5-9,12,26H,4,10-11H2,1-3H3

> <INCHI_KEY>
SXMWAVZXRLTFTM-UHFFFAOYSA-N

> <FORMULA>
C23H22O5

> <MOLECULAR_WEIGHT>
378.424

> <EXACT_MASS>
378.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
41.15000728468025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-12,12-dimethyl-6-phenyl-9-propanoyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
4.845113835666668

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.567609625772555

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5695663750035065

> <JCHEM_PKA_STRONGEST_BASIC>
-4.931168222484717

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
115.54270000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.91e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-12,12-dimethyl-6-phenyl-9-propanoyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    1.9356    1.2545    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249    1.7257    2.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1861    1.4299    1.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112    1.3355    2.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    1.1843    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4816    1.8381   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517    1.5250   -1.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8804    0.5981   -2.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861    0.3480   -3.5807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -0.5331   -3.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4416   -0.7549   -5.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102   -1.1974   -2.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6608   -0.9923   -1.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5305   -1.7704   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1567   -3.0584   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9945   -3.8041    0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2097   -3.2700    0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5893   -1.9896    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7540   -1.2412   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864   -0.0445   -1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2178    0.2694    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941   -0.3420    1.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    2.1912   -3.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1323    2.8663   -2.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075    3.6435   -1.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416    4.8263   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2571    4.1817   -0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237    2.7790   -0.3425 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    1.4410    3.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7426    0.1818    3.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3197    1.7808    4.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    1.2122    1.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7902    2.8059    2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838   -1.8784   -3.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086   -3.4823   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6965   -4.7996    0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8590   -3.8499    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5336   -1.5715    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0575   -0.2416   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219    0.1478    1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016    1.4550   -3.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1719    2.9261   -3.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8863    2.0854   -2.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5173    3.5154   -3.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2886    5.5218   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    4.4995   -1.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    5.3767   -0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405    4.7089    0.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7106    4.8678   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9590    3.3609   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  8  1  0
 18 19  2  0
 19 14  1  0
 13 14  1  0
  7  6  1  0
 20 13  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 12 13  2  0
  7 23  1  0
  6 28  1  0
 28 25  1  0
 25 24  1  0
 24 23  1  0
  5  6  2  0
 25 26  1  0
 14 15  2  0
 25 27  1  0
  5 21  1  0
 10 11  2  0
 15 16  1  0
 21 22  1  0
  7  8  2  0
  5  3  1  0
 16 17  2  0
  3  4  2  0
 20 21  2  0
  3  2  1  0
 17 18  1  0
  2  1  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 24 43  1  0
 24 44  1  0
 23 41  1  0
 23 42  1  0
 26 45  1  0
 26 46  1  0
 26 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
 22 40  1  0
  2 32  1  0
  2 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  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       1.936   1.254   3.622  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.625   1.726   2.210  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.186   1.430   1.828  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.711   1.335   2.669  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.174   1.184   0.398  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.482   1.838  -0.659  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.152   1.525  -1.983  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.880   0.598  -2.223  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.186   0.348  -3.581  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.178  -0.533  -3.962  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.442  -0.755  -5.137  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.910  -1.197  -2.882  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.661  -0.992  -1.578  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.531  -1.770  -0.672  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.157  -3.058  -0.266  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.994  -3.804   0.566  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.210  -3.270   0.993  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.589  -1.990   0.592  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.754  -1.241  -0.240  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.586  -0.045  -1.200  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.218   0.269   0.120  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.894  -0.342   1.149  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.850   2.191  -3.137  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.132   2.866  -2.683  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.908   3.644  -1.384  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.942   4.826  -1.547  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.257   4.182  -0.887  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.424   2.779  -0.343  0.00  0.00           O+0
HETATM   29  H   UNK     0       2.987   1.441   3.863  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.743   0.182   3.729  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.320   1.781   4.359  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.303   1.212   1.521  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.790   2.806   2.148  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.684  -1.878  -3.224  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.209  -3.482  -0.586  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.696  -4.800   0.884  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.859  -3.850   1.644  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.534  -1.571   0.930  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.058  -0.242  -0.540  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.722   0.148   1.985  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.102   1.455  -3.910  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.172   2.926  -3.587  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.886   2.085  -2.511  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.517   3.515  -3.478  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.289   5.522  -2.318  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.070   4.500  -1.809  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.843   5.377  -0.604  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.140   4.709   0.067  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.711   4.868  -1.610  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.959   3.361  -0.699  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1   32   33                                             
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6   21    3                                                  
CONECT    6    7   28    5                                                  
CONECT    7    6   23    8                                                  
CONECT    8   20    9    7                                                  
CONECT    9    8   10                                                       
CONECT   10    9   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   13   34                                                  
CONECT   13   14   20   12                                                  
CONECT   14   19   13   15                                                  
CONECT   15   14   16   35                                                  
CONECT   16   15   17   36                                                  
CONECT   17   16   18   37                                                  
CONECT   18   19   17   38                                                  
CONECT   19   18   14   39                                                  
CONECT   20    8   13   21                                                  
CONECT   21    5   22   20                                                  
CONECT   22   21   40                                                       
CONECT   23    7   24   41   42                                             
CONECT   24   25   23   43   44                                             
CONECT   25   28   24   26   27                                             
CONECT   26   25   45   46   47                                             
CONECT   27   25   48   49   50                                             
CONECT   28    6   25                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    2                                                            
CONECT   34   12                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   22                                                            
CONECT   41   23                                                            
CONECT   42   23                                                            
CONECT   43   24                                                            
CONECT   44   24                                                            
CONECT   45   26                                                            
CONECT   46   26                                                            
CONECT   47   26                                                            
CONECT   48   27                                                            
CONECT   49   27                                                            
CONECT   50   27                                                            
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
    1.9356    1.2545    3.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6249    1.7257    2.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1861    1.4299    1.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7112    1.3355    2.6692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    1.1843    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4816    1.8381   -0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1517    1.5250   -1.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8804    0.5981   -2.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861    0.3480   -3.5807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1780   -0.5331   -3.9617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4416   -0.7549   -5.1372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102   -1.1974   -2.8822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6608   -0.9923   -1.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5305   -1.7704   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1567   -3.0584   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9945   -3.8041    0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2097   -3.2700    0.9929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5893   -1.9896    0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7540   -1.2412   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864   -0.0445   -1.2002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2178    0.2694    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8941   -0.3420    1.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8498    2.1912   -3.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1323    2.8663   -2.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9075    3.6435   -1.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416    4.8263   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2571    4.1817   -0.8868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4237    2.7790   -0.3425 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    1.4410    3.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7426    0.1818    3.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3197    1.7808    4.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    1.2122    1.5207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7902    2.8059    2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838   -1.8784   -3.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2086   -3.4823   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6965   -4.7996    0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8590   -3.8499    1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5336   -1.5715    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0575   -0.2416   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219    0.1478    1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016    1.4550   -3.9096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1719    2.9261   -3.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8863    2.0854   -2.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5173    3.5154   -3.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2886    5.5218   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0700    4.4995   -1.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8433    5.3767   -0.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1405    4.7089    0.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7106    4.8678   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9590    3.3609   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  8  1  0
 18 19  2  0
 19 14  1  0
 13 14  1  0
  7  6  1  0
 20 13  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 12 13  2  0
  7 23  1  0
  6 28  1  0
 28 25  1  0
 25 24  1  0
 24 23  1  0
  5  6  2  0
 25 26  1  0
 14 15  2  0
 25 27  1  0
  5 21  1  0
 10 11  2  0
 15 16  1  0
 21 22  1  0
  7  8  2  0
  5  3  1  0
 16 17  2  0
  3  4  2  0
 20 21  2  0
  3  2  1  0
 17 18  1  0
  2  1  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 24 43  1  0
 24 44  1  0
 23 41  1  0
 23 42  1  0
 26 45  1  0
 26 46  1  0
 26 47  1  0
 27 48  1  0
 27 49  1  0
 27 50  1  0
 22 40  1  0
  2 32  1  0
  2 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₅

Average Mass

378.4240 Da

Monoisotopic Mass

378.14672 Da

IUPAC Name

8-hydroxy-12,12-dimethyl-6-phenyl-9-propanoyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

Traditional Name

8-hydroxy-12,12-dimethyl-6-phenyl-9-propanoyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(OC(=O)C([H])=C2C2=C([H])C([H])=C([H])C([H])=C2[H])=C2C(OC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C2([H])[H])=C1C(=O)C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H22O5/c1-4-16(24)19-20(26)18-15(13-8-6-5-7-9-13)12-17(25)27-21(18)14-10-11-23(2,3)28-22(14)19/h5-9,12,26H,4,10-11H2,1-3H3

InChI Key

SXMWAVZXRLTFTM-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Marila pluricostata	JEOL database	Lopez-Perez, J. L., et al, J. Nat. Prod. 68, 369 (2005)

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
Pyranoneoflavonoid
4-phenylcoumarin
Pyranocoumarin
Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Coumarin
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Ketone
Lactone
Ether
Oxacycle
Organoheterocyclic compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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	4.98	ALOGPS
logP	4.85	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.54 m³·mol⁻¹	ChemAxon
Polarizability	41.15 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

9409346

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11234299

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lopez-Perez, J. L., et al. (2005). Lopez-Perez, J. L., et al, J. Nat. Prod. 68, 369 (2005). J. Nat. Prod..

Showing NP-Card for 5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+ (NP0028018)

MOL for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

3D MOL for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

3D SDF for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

3D-SDF for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

PDB for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

3D PDB for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

SMILES for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

INCHI for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

Structure for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)

3D Structure for NP0028018 (5-hydroxy-8,8-dimethyl-4-phenyl-6-propionyl-9,10-dihydro-8H-pyrano-[2,3-f+)