NP-MRD: Showing NP-Card for (+)-crassalactone C (NP0032551)

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Record Information

Version

2.0

Created at

2021-06-19 23:19:27 UTC

Updated at

2021-06-30 00:01:49 UTC

NP-MRD ID

NP0032551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-crassalactone C

Provided By

JEOL Database JEOL Logo

Description

Crassalactone C belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. (+)-crassalactone C is found in Polyalthia crassa. (+)-crassalactone C was first documented in 2007 (PMID: 17867695). Based on a literature review a small amount of articles have been published on Crassalactone C (PMID: 20359789) (PMID: 18783950).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101193D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202101193D          

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 27 19  1  0  0  0  0
 23 24  2  0  0  0  0
  7  8  2  0  0  0  0
 21 43  1  6  0  0  0
 19 12  1  0  0  0  0
 26 46  1  1  0  0  0
 27 28  1  0  0  0  0
 11  2  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  2  0  0  0  0
  3 29  1  0  0  0  0
  4 30  1  0  0  0  0
  6 31  1  0  0  0  0
  7 32  1  0  0  0  0
  8 33  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  0  0  0  0
 28 48  1  0  0  0  0
 19 42  1  1  0  0  0
 27 47  1  1  0  0  0
 12 36  1  6  0  0  0
 18 41  1  0  0  0  0
 14 37  1  0  0  0  0
 15 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@@]([H])(O[C@@]2([H])C([H])([H])C(=O)O[C@@]12[H])[C@@]([H])(OC(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O6/c23-17(12-11-14-7-3-1-4-8-14)27-20(15-9-5-2-6-10-15)22-19(25)21-16(26-22)13-18(24)28-21/h1-12,16,19-22,25H,13H2/b12-11+/t16-,19-,20-,21+,22+/m0/s1

> <INCHI_KEY>
GDYNBHXFRSGEGM-GVUDQUTJSA-N

> <FORMULA>
C22H20O6

> <MOLECULAR_WEIGHT>
380.396

> <EXACT_MASS>
380.125988364

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
39.88365121165152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(S)-[(2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydrofuro[3,2-b]furan-2-yl](phenyl)methyl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.3193848103333328

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.014169263420861

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6674023641797158

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
99.7435

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-[(2R,3R,3aS,6aS)-3-hydroxy-5-oxo-tetrahydro-2H-furo[3,2-b]furan-2-yl](phenyl)methyl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 48 51  0  0  0  0  0  0  0  0999 V2000
    0.4459    3.3680   -1.0580 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    2.3348   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5115    2.2443   -1.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440    3.3627   -1.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6839    3.3710   -1.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2747    2.4674   -2.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6449    2.5270   -3.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4358    3.4961   -2.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8571    4.4104   -1.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    4.3517   -1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821    1.0810   -1.1294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469    0.9430   -0.9471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2440   -0.3109   -1.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547   -0.2839   -2.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362   -1.4259   -3.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155   -2.6095   -3.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -2.6540   -2.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -1.5134   -1.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985    0.8214    0.5500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6033    0.5182    0.7515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185    1.1103    1.9984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4008    0.0456    2.9905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1106   -0.1993    3.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853   -1.1418    4.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2127    0.7991    3.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131    1.7792    2.6135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9414    2.0696    1.4078 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4305    3.2721    0.8112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9310    1.2527   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857    4.3393   -1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6779    1.7148   -3.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0930    1.8201   -3.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5012    3.5429   -2.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4708    5.1716   -1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    5.0766   -0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    1.7927   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9386    0.6268   -2.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6000   -1.3924   -3.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -3.4984   -3.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -3.5785   -2.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.5698   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6342   -0.0162    0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8377    1.7992    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1292    0.4156    3.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472   -0.8722    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    2.6620    3.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1161    2.1902    1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852    3.5567    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  8  9  1  0
 18 13  1  0
 13 14  2  0
  9 10  2  0
 14 15  1  0
 10  5  1  0
 15 16  2  0
  5  6  2  0
 16 17  1  0
 17 18  2  0
 12 11  1  0
 19 20  1  0
 26 21  1  0
  3  4  2  0
  6  7  1  0
  4  5  1  0
 20 21  1  0
 26 27  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 25 26  1  0
 27 19  1  0
 23 24  2  0
  7  8  2  0
 21 43  1  6
 19 12  1  0
 26 46  1  1
 27 28  1  0
 11  2  1  0
 12 13  1  0
  2  1  2  0
  3 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 28 48  1  0
 19 42  1  1
 27 47  1  1
 12 36  1  6
 18 41  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 22 44  1  0
 22 45  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  O   UNK     0       0.446   3.368  -1.058  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.072   2.335  -1.226  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.511   2.244  -1.535  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.244   3.363  -1.644  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.684   3.371  -1.935  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.275   2.467  -2.829  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.645   2.527  -3.097  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.436   3.496  -2.484  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.857   4.410  -1.607  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.487   4.352  -1.339  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.582   1.081  -1.129  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.847   0.943  -0.947  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.244  -0.311  -1.718  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.355  -0.284  -2.576  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.736  -1.426  -3.283  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.015  -2.610  -3.140  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.914  -2.654  -2.288  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.531  -1.513  -1.580  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.198   0.821   0.550  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.603   0.518   0.752  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.018   1.110   1.998  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.401   0.046   2.990  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.111  -0.199   3.709  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.885  -1.142   4.451  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.213   0.799   3.464  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.813   1.779   2.614  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.941   2.070   1.408  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.431   3.272   0.811  0.00  0.00           O+0
HETATM   29  H   UNK     0       2.931   1.253  -1.652  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.786   4.339  -1.495  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.678   1.715  -3.338  0.00  0.00           H+0
HETATM   32  H   UNK     0       7.093   1.820  -3.791  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.501   3.543  -2.695  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.471   5.172  -1.132  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.056   5.077  -0.652  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.375   1.793  -1.399  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.939   0.627  -2.693  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.600  -1.392  -3.941  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.315  -3.498  -3.688  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.354  -3.579  -2.172  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.331  -1.570  -0.919  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.634  -0.016   0.983  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.838   1.799   1.772  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.129   0.416   3.717  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.747  -0.872   2.510  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.069   2.662   3.209  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.116   2.190   1.662  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.785   3.557   0.126  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3   11    1                                                  
CONECT    3    2    4   29                                                  
CONECT    4    3    5   30                                                  
CONECT    5   10    6    4                                                  
CONECT    6    5    7   31                                                  
CONECT    7    6    8   32                                                  
CONECT    8    9    7   33                                                  
CONECT    9    8   10   34                                                  
CONECT   10    9    5   35                                                  
CONECT   11   12    2                                                       
CONECT   12   11   19   13   36                                             
CONECT   13   18   14   12                                                  
CONECT   14   13   15   37                                                  
CONECT   15   14   16   38                                                  
CONECT   16   15   17   39                                                  
CONECT   17   16   18   40                                                  
CONECT   18   13   17   41                                                  
CONECT   19   20   27   12   42                                             
CONECT   20   19   21                                                       
CONECT   21   26   20   22   43                                             
CONECT   22   21   23   44   45                                             
CONECT   23   22   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   21   27   25   46                                             
CONECT   27   26   19   28   47                                             
CONECT   28   27   48                                                       
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   12                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   21                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   26                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  102    0
END

RDKit          3D

48 51  0  0  0  0  0  0  0  0999 V2000
    0.4459    3.3680   -1.0580 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    2.3348   -1.2261 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5115    2.2443   -1.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440    3.3627   -1.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6839    3.3710   -1.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2747    2.4674   -2.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6449    2.5270   -3.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4358    3.4961   -2.4840 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8571    4.4104   -1.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    4.3517   -1.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5821    1.0810   -1.1294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8469    0.9430   -0.9471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2440   -0.3109   -1.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547   -0.2839   -2.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362   -1.4259   -3.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0155   -2.6095   -3.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9140   -2.6540   -2.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306   -1.5134   -1.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1985    0.8214    0.5500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6033    0.5182    0.7515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0185    1.1103    1.9984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4008    0.0456    2.9905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1106   -0.1993    3.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853   -1.1418    4.4508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2127    0.7991    3.4636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8131    1.7792    2.6135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9414    2.0696    1.4078 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4305    3.2721    0.8112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9310    1.2527   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7857    4.3393   -1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6779    1.7148   -3.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0930    1.8201   -3.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5012    3.5429   -2.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4708    5.1716   -1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0556    5.0766   -0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    1.7927   -1.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9386    0.6268   -2.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6000   -1.3924   -3.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3153   -3.4984   -3.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543   -3.5785   -2.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.5698   -0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6342   -0.0162    0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8377    1.7992    1.7724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1292    0.4156    3.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7472   -0.8722    2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0686    2.6620    3.2086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1161    2.1902    1.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7852    3.5567    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  8  9  1  0
 18 13  1  0
 13 14  2  0
  9 10  2  0
 14 15  1  0
 10  5  1  0
 15 16  2  0
  5  6  2  0
 16 17  1  0
 17 18  2  0
 12 11  1  0
 19 20  1  0
 26 21  1  0
  3  4  2  0
  6  7  1  0
  4  5  1  0
 20 21  1  0
 26 27  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 25 26  1  0
 27 19  1  0
 23 24  2  0
  7  8  2  0
 21 43  1  6
 19 12  1  0
 26 46  1  1
 27 28  1  0
 11  2  1  0
 12 13  1  0
  2  1  2  0
  3 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 28 48  1  0
 19 42  1  1
 27 47  1  1
 12 36  1  6
 18 41  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 22 44  1  0
 22 45  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀O₆

Average Mass

380.3960 Da

Monoisotopic Mass

380.12599 Da

IUPAC Name

(S)-[(2R,3R,3aS,6aS)-3-hydroxy-5-oxo-hexahydrofuro[3,2-b]furan-2-yl](phenyl)methyl (2E)-3-phenylprop-2-enoate

Traditional Name

(S)-[(2R,3R,3aS,6aS)-3-hydroxy-5-oxo-tetrahydro-2H-furo[3,2-b]furan-2-yl](phenyl)methyl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@@]([H])(O[C@@]2([H])C([H])([H])C(=O)O[C@@]12[H])[C@@]([H])(OC(=O)C(\[H])=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H])C1=C([H])C([H])=C([H])C([H])=C1[H]

InChI Identifier

InChI=1S/C22H20O6/c23-17(12-11-14-7-3-1-4-8-14)27-20(15-9-5-2-6-10-15)22-19(25)21-16(26-22)13-18(24)28-21/h1-12,16,19-22,25H,13H2/b12-11+/t16-,19-,20-,21+,22+/m0/s1

InChI Key

GDYNBHXFRSGEGM-GVUDQUTJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Marsypopetalum crassum	JEOL database	Tuchinda, P., et al, J. Nat. Prod. 69, 1728 (2006)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Benzyloxycarbonyl
Furofuran
Styrene
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Gamma butyrolactone
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen 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	3.01	ALOGPS
logP	3.32	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.01	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.74 m³·mol⁻¹	ChemAxon
Polarizability	39.88 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	Yes	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

23339176

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44566460

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Popsavin V, Sreco B, Benedekovic G, Francuz J, Popsavin M, Kojic V, Bogdanovic G: Design, synthesis and antiproliferative activity of styryl lactones related to (+)-goniofufurone. Eur J Med Chem. 2010 Jul;45(7):2876-83. doi: 10.1016/j.ejmech.2010.03.010. Epub 2010 Mar 12. [PubMed:20359789 ]
Popsavin V, Benedekovic G, Sreco B, Popsavin M, Francuz J, Kojic V, Bogdanovic G: Synthesis and antiproliferative activity of unnatural enantiomers of 7-epi-goniofufurone and crassalactone C. Bioorg Med Chem Lett. 2008 Oct 1;18(19):5178-81. doi: 10.1016/j.bmcl.2008.08.093. Epub 2008 Aug 29. [PubMed:18783950 ]
Popsavin V, Benedekovic G, Sreco B, Popsavin M, Francuz J, Kojic V, Bogdanovic G: Divergent synthesis of cytotoxic styryl lactones from D-xylose. The first total synthesis of (+)-crassalactone C. Org Lett. 2007 Oct 11;9(21):4235-8. doi: 10.1021/ol701734s. Epub 2007 Sep 15. [PubMed:17867695 ]
Tuchinda, P., et al. (2006). Tuchinda, P., et al, J. Nat. Prod. 69, 1728 (2006) . J. Nat. Prod..

Showing NP-Card for (+)-crassalactone C (NP0032551)

MOL for NP0032551 ((+)-crassalactone C)

3D MOL for NP0032551 ((+)-crassalactone C)

3D SDF for NP0032551 ((+)-crassalactone C)

3D-SDF for NP0032551 ((+)-crassalactone C)

PDB for NP0032551 ((+)-crassalactone C)

3D PDB for NP0032551 ((+)-crassalactone C)

SMILES for NP0032551 ((+)-crassalactone C)

INCHI for NP0032551 ((+)-crassalactone C)

Structure for NP0032551 ((+)-crassalactone C)

3D Structure for NP0032551 ((+)-crassalactone C)