NP-MRD: Showing NP-Card for 1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial (NP0038047)

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Record Information

Version

2.0

Created at

2021-06-20 20:50:09 UTC

Updated at

2021-06-30 00:10:37 UTC

NP-MRD ID

NP0038047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial

Provided By

JEOL Database JEOL Logo

Description

(1R,4aS,5S,8S,8aS)-7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. 1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial is found in Zygogynum acsmithii (Winteraceae) and Zygogynum pancheri. 1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial was first documented in 2009 (Allouche, N., et al.). Based on a literature review very few articles have been published on (1R,4aS,5S,8S,8aS)-7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122503D          

 57 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202122503D          

 57 59  0  0  0  0            999 V2000
   -0.6448    0.4813    3.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    0.5196    2.5475 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7184    1.4437    4.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0262   -0.2767    4.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    0.3003    3.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825    1.9984    3.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    0.3450    3.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562    0.9309    2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6106    1.8622    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341    2.5585    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515    1.1885    1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    2.0896    0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    0.1686   -0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7150   -0.8505   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037    0.9465   -3.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -0.1162   -5.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278   -0.7118   -6.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4818   -1.0300   -5.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2257   -0.7327   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428   -0.1244   -1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -2.3539    2.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771   -2.1913    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -0.8315    2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -2.8488   -0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7412   -2.0898   -2.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -5.7377    0.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -4.2364    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649   -2.1210    3.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603   -1.8547    1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359   -0.6590    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 29  1  0  0  0  0
 27 28  1  0  0  0  0
 18  6  1  0  0  0  0
 23 24  1  0  0  0  0
 18 20  1  0  0  0  0
 24 53  1  0  0  0  0
 29 27  1  0  0  0  0
 24 25  2  0  0  0  0
 27 26  1  0  0  0  0
 21 52  1  0  0  0  0
 26 23  2  0  0  0  0
 21 22  2  0  0  0  0
 23 20  1  0  0  0  0
 29 57  1  6  0  0  0
 18 29  1  0  0  0  0
  7  8  1  0  0  0  0
  6  7  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 18 19  1  1  0  0  0
 10 11  2  0  0  0  0
  5  4  1  0  0  0  0
 11 12  1  0  0  0  0
 20 21  1  0  0  0  0
 12 13  2  0  0  0  0
  5  6  1  0  0  0  0
 13 14  1  0  0  0  0
  2  1  1  1  0  0  0
 14 15  2  0  0  0  0
  4  2  1  0  0  0  0
 15 16  1  0  0  0  0
  2  3  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
  5 38  1  0  0  0  0
  5 39  1  0  0  0  0
  4 36  1  0  0  0  0
  4 37  1  0  0  0  0
  6 40  1  6  0  0  0
 27 55  1  1  0  0  0
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 20 51  1  6  0  0  0
 19 48  1  0  0  0  0
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  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
 28 56  1  0  0  0  0
 10 41  1  0  0  0  0
 11 42  1  0  0  0  0
 13 43  1  0  0  0  0
 14 44  1  0  0  0  0
 15 45  1  0  0  0  0
 16 46  1  0  0  0  0
 17 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])=C(C([H])=O)[C@@]([H])(C([H])=O)[C@@]2(C([H])([H])[H])[C@]([H])(OC(=O)C(\[H])=C(/[H])C3=C([H])C([H])=C([H])C([H])=C3[H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H28O5/c1-23(2)12-11-20(29-21(28)10-9-16-7-5-4-6-8-16)24(3)18(15-26)17(14-25)13-19(27)22(23)24/h4-10,13-15,18-20,22,27H,11-12H2,1-3H3/b10-9+/t18-,19+,20-,22+,24+/m1/s1

> <INCHI_KEY>
RJMZKVMAXFDSJD-UPCCYMMLSA-N

> <FORMULA>
C24H28O5

> <MOLECULAR_WEIGHT>
396.483

> <EXACT_MASS>
396.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.43310944255093

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aS,5S,8S,8aS)-7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.18

> <JCHEM_LOGP>
3.182841483

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.660637474427574

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.246352243782894

> <JCHEM_PKA_STRONGEST_BASIC>
-3.02525936123925

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
111.62840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4aS,5S,8S,8aS)-7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
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    5.1716   -0.2524   -5.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4161   -0.5903   -5.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5132   -0.7690   -4.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3679   -0.6047   -3.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1230   -0.2674   -2.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -1.2304    0.9843 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9873   -1.6707    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4595   -2.4692    0.0534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3003   -2.1412   -1.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5069   -1.9102   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738   -3.5815    0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938   -4.9419    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4527   -5.1649   -0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677   -3.4013    1.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393   -2.0637    2.5724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4382   -1.9228    2.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7341    2.5585    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515    1.1885    1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    2.0896    0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    0.1686   -0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7150   -0.8505   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037    0.9465   -3.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -0.1162   -5.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278   -0.7118   -6.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4818   -1.0300   -5.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2257   -0.7327   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428   -0.1244   -1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -2.3539    2.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771   -2.1913    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -0.8315    2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -2.8488   -0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7412   -2.0898   -2.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -5.7377    0.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -4.2364    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649   -2.1210    3.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603   -1.8547    1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359   -0.6590    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 29  1  0
 27 28  1  0
 18  6  1  0
 23 24  1  0
 18 20  1  0
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 29 27  1  0
 24 25  2  0
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 21 52  1  0
 26 23  2  0
 21 22  2  0
 23 20  1  0
 29 57  1  6
 18 29  1  0
  7  8  1  0
  6  7  1  0
  8  9  2  0
  8 10  1  0
 18 19  1  1
 10 11  2  0
  5  4  1  0
 11 12  1  0
 20 21  1  0
 12 13  2  0
  5  6  1  0
 13 14  1  0
  2  1  1  1
 14 15  2  0
  4  2  1  0
 15 16  1  0
  2  3  1  0
 16 17  2  0
 17 12  1  0
  5 38  1  0
  5 39  1  0
  4 36  1  0
  4 37  1  0
  6 40  1  6
 27 55  1  1
 26 54  1  0
 20 51  1  6
 19 48  1  0
 19 49  1  0
 19 50  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
 28 56  1  0
 10 41  1  0
 11 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  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      -0.645   0.481   3.864  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.446   0.520   2.547  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.880   0.967   2.934  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.875   1.629   1.625  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.436   1.266   0.942  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.296  -0.019   0.122  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.564  -0.341  -0.485  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.837   0.262  -1.670  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.103   1.014  -2.287  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.183  -0.166  -2.097  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.688   0.280  -3.257  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.008  -0.101  -3.776  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.172  -0.252  -5.159  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.416  -0.590  -5.697  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.513  -0.769  -4.857  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.368  -0.605  -3.481  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.123  -0.267  -2.943  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.169  -1.230   0.984  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.987  -1.671   1.933  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.460  -2.469   0.053  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.300  -2.141  -1.178  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.507  -1.910  -1.147  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.174  -3.582   0.777  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.094  -4.942   0.192  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.453  -5.165  -0.829  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.868  -3.401   1.912  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.039  -2.064   2.572  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.438  -1.923   2.785  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.487  -0.852   1.761  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.718   1.444   4.386  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.026  -0.277   4.554  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.418   0.300   3.718  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.882   1.998   3.307  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.302   0.345   3.729  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.556   0.931   2.072  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.611   1.862   0.843  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.734   2.559   2.192  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.252   1.188   1.669  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.733   2.090   0.280  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.451   0.169  -0.660  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.715  -0.851  -1.449  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.104   0.947  -3.890  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.328  -0.116  -5.833  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.528  -0.712  -6.771  0.00  0.00           H+0
HETATM   45  H   UNK     0       8.482  -1.030  -5.275  0.00  0.00           H+0
HETATM   46  H   UNK     0       8.226  -0.733  -2.826  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.043  -0.124  -1.869  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.653  -2.354   2.719  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.777  -2.191   1.378  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.483  -0.832   2.421  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.496  -2.849  -0.334  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.741  -2.090  -2.129  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.640  -5.738   0.726  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.356  -4.236   2.410  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.565  -2.121   3.556  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.860  -1.855   1.909  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.236  -0.659   0.978  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2   29    1    4    3                                             
CONECT    3    2   33   34   35                                             
CONECT    4    5    2   36   37                                             
CONECT    5    4    6   38   39                                             
CONECT    6   18    7    5   40                                             
CONECT    7    8    6                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   41                                                  
CONECT   11   10   12   42                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   43                                                  
CONECT   14   13   15   44                                                  
CONECT   15   14   16   45                                                  
CONECT   16   15   17   46                                                  
CONECT   17   16   12   47                                                  
CONECT   18    6   20   29   19                                             
CONECT   19   18   48   49   50                                             
CONECT   20   18   23   21   51                                             
CONECT   21   52   22   20                                                  
CONECT   22   21                                                            
CONECT   23   24   26   20                                                  
CONECT   24   23   53   25                                                  
CONECT   25   24                                                            
CONECT   26   27   23   54                                                  
CONECT   27   28   29   26   55                                             
CONECT   28   27   56                                                       
CONECT   29    2   27   57   18                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    5                                                            
CONECT   40    6                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   13                                                            
CONECT   44   14                                                            
CONECT   45   15                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   24                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
   -0.6448    0.4813    3.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    0.5196    2.5475 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8797    0.9672    2.9335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8749    1.6291    1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    1.2660    0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2961   -0.0188    0.1221 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5643   -0.3405   -0.4851 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8367    0.2617   -1.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    1.0137   -2.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1827   -0.1663   -2.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6877    0.2797   -3.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0082   -0.1012   -3.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716   -0.2524   -5.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4161   -0.5903   -5.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5132   -0.7690   -4.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3679   -0.6047   -3.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1230   -0.2674   -2.9430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -1.2304    0.9843 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9873   -1.6707    1.9334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4595   -2.4692    0.0534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3003   -2.1412   -1.1775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5069   -1.9102   -1.1472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1738   -3.5815    0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938   -4.9419    0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4527   -5.1649   -0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677   -3.4013    1.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393   -2.0637    2.5724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4382   -1.9228    2.7854 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871   -0.8521    1.7613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7184    1.4437    4.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0262   -0.2767    4.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    0.3003    3.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8825    1.9984    3.3071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    0.3450    3.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562    0.9309    2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6106    1.8622    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341    2.5585    2.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2515    1.1885    1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7329    2.0896    0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509    0.1686   -0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7150   -0.8505   -1.4487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1037    0.9465   -3.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -0.1162   -5.8326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278   -0.7118   -6.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4818   -1.0300   -5.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2257   -0.7327   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428   -0.1244   -1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527   -2.3539    2.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7771   -2.1913    1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -0.8315    2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4959   -2.8488   -0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7412   -2.0898   -2.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399   -5.7377    0.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3557   -4.2364    2.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5649   -2.1210    3.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603   -1.8547    1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2359   -0.6590    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 29  1  0
 27 28  1  0
 18  6  1  0
 23 24  1  0
 18 20  1  0
 24 53  1  0
 29 27  1  0
 24 25  2  0
 27 26  1  0
 21 52  1  0
 26 23  2  0
 21 22  2  0
 23 20  1  0
 29 57  1  6
 18 29  1  0
  7  8  1  0
  6  7  1  0
  8  9  2  0
  8 10  1  0
 18 19  1  1
 10 11  2  0
  5  4  1  0
 11 12  1  0
 20 21  1  0
 12 13  2  0
  5  6  1  0
 13 14  1  0
  2  1  1  1
 14 15  2  0
  4  2  1  0
 15 16  1  0
  2  3  1  0
 16 17  2  0
 17 12  1  0
  5 38  1  0
  5 39  1  0
  4 36  1  0
  4 37  1  0
  6 40  1  6
 27 55  1  1
 26 54  1  0
 20 51  1  6
 19 48  1  0
 19 49  1  0
 19 50  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  3 35  1  0
 28 56  1  0
 10 41  1  0
 11 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 16 46  1  0
 17 47  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(1R,4AS,5S,8S,8as)-7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₄H₂₈O₅

Average Mass

396.4830 Da

Monoisotopic Mass

396.19367 Da

IUPAC Name

(1R,4aS,5S,8S,8aS)-7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,4aS,5S,8S,8aS)-7,8-diformyl-5-hydroxy-4,4,8a-trimethyl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])=C(C([H])=O)[C@@]([H])(C([H])=O)[C@@]2(C([H])([H])[H])[C@]([H])(OC(=O)C(\[H])=C(/[H])C3=C([H])C([H])=C([H])C([H])=C3[H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]12[H]

InChI Identifier

InChI=1S/C24H28O5/c1-23(2)12-11-20(29-21(28)10-9-16-7-5-4-6-8-16)24(3)18(15-26)17(14-25)13-19(27)22(23)24/h4-10,13-15,18-20,22,27H,11-12H2,1-3H3/b10-9+/t18-,19+,20-,22+,24+/m1/s1

InChI Key

RJMZKVMAXFDSJD-UPCCYMMLSA-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

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
Zygogynum acsmithii	JEOL database	Allouche, N., et al, Phytochemistry 70, 546 (2009)
Zygogynum pancheri	JEOL database	Allouche, N., et al, Phytochemistry 70, 546 (2009)

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
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Aldehyde
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.18	ALOGPS
logP	3.18	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	111.63 m³·mol⁻¹	ChemAxon
Polarizability	43.43 Å³	ChemAxon
Number of Rings	3	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42611763

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Allouche, N., et al. (2009). Allouche, N., et al, Phytochemistry 70, 546 (2009). Phytochem..

Showing NP-Card for 1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial (NP0038047)

MOL for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

3D MOL for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

3D SDF for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

3D-SDF for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

PDB for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

3D PDB for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

SMILES for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

INCHI for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

Structure for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)

3D Structure for NP0038047 (1beta-O-E-cinnamoyl-6alpha-hydroxy-9-epipolygodial)