NP-MRD: Showing NP-Card for dysidavarone A (NP0041432)

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Record Information

Version

1.0

Created at

2021-06-20 23:20:32 UTC

Updated at

2021-06-30 00:15:56 UTC

NP-MRD ID

NP0041432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dysidavarone A

Provided By

JEOL Database JEOL Logo

Description

Dysidavarone A belongs to the class of organic compounds known as vinylogous esters. These are organic compounds containing an ester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. dysidavarone A is found in Dysidea avara. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on Dysidavarone A (PMID: 33079503) (PMID: 26389513) (PMID: 24482283) (PMID: 23391209).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101203D          

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     RDKit          3D

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  Mrv1652306212101203D          

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    0.2668   -1.2422   -4.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9591    0.2846   -3.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120   -0.6882   -1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092    0.6289   -2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0174   -0.7298   -3.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749    0.8304   -3.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    1.5460   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2873    1.5016   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -0.1192    4.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817    2.7683    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740    4.0708    2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550    2.9828    3.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    4.5278    3.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726    4.2643    4.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5  7  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9  7  2  0  0  0  0
  3  4  1  0  0  0  0
 18 19  2  0  0  0  0
  4  5  1  0  0  0  0
 25 26  2  0  0  0  0
 16 25  1  0  0  0  0
 21 22  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  6  0  0  0
 18 20  1  0  0  0  0
  5  6  1  6  0  0  0
 20 21  2  0  0  0  0
 13  2  1  0  0  0  0
  3  2  1  0  0  0  0
 21 25  1  0  0  0  0
  7  8  1  0  0  0  0
  5 12  1  0  0  0  0
  2  1  2  3  0  0  0
 12 13  1  0  0  0  0
 12 43  1  1  0  0  0
 16 17  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  3 17  1  0  0  0  0
 15 47  1  0  0  0  0
 15 48  1  0  0  0  0
  3 29  1  1  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
 20 49  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
  9 38  1  0  0  0  0
 14 44  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 24 54  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1[C@]2([H])C3=C(C(=O)C(OC([H])([H])C([H])([H])[H])=C([H])C3=O)C([H])([H])[C@@]1(C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])[C@@]1(C([H])([H])[H])C2([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O3/c1-6-26-18-10-17(24)20-15-11-22(4)13(2)8-7-9-19(22)23(5,14(15)3)12-16(20)21(18)25/h8,10,15,19H,3,6-7,9,11-12H2,1-2,4-5H3/t15-,19-,22-,23-/m1/s1

> <INCHI_KEY>
OMLKNXFIVARPQF-BHAGSQDASA-N

> <FORMULA>
C23H28O3

> <MOLECULAR_WEIGHT>
352.474

> <EXACT_MASS>
352.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.07482786085652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9S,10R,15S)-5-ethoxy-9,14,15-trimethyl-17-methylidenetetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2(7),4,13-triene-3,6-dione

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
4.166841595333333

> <ALOGPS_LOGS>
-4.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.956465015420151

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
105.67789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S,10R,15S)-5-ethoxy-9,14,15-trimethyl-17-methylidenetetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2(7),4,13-triene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.9185   -1.4835   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980   -1.2326   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565   -1.8030    0.5109 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2864   -2.8323   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5125   -2.6411   -1.7021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5657   -3.4022   -2.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -3.2524   -2.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520   -4.6045   -1.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -2.6320   -3.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -1.3189   -3.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537   -0.7956   -3.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -1.0984   -1.9981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8350   -0.3553   -1.5309 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7042    0.1126   -2.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4220    0.9085   -0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    0.5701    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015   -0.6641    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7112   -0.9563    2.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -2.0610    3.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    0.1314    3.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5543    1.3575    2.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    2.3041    3.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0173    3.2447    2.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1077    3.7916    3.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003    1.6755    1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325    2.7958    0.8483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -1.0783   -1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3579   -2.1181    0.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -2.3225    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -3.8381    0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2528   -2.8114    0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341   -3.4071   -3.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369   -4.4502   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -2.9816   -2.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -4.9935   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594   -5.3390   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553   -4.5493   -0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6094   -3.0935   -3.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -0.5854   -3.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5348   -1.4059   -4.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -1.2422   -4.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9591    0.2846   -3.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120   -0.6882   -1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092    0.6289   -2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0174   -0.7298   -3.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749    0.8304   -3.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    1.5460   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2873    1.5016   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -0.1192    4.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817    2.7683    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740    4.0708    2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550    2.9828    3.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    4.5278    3.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726    4.2643    4.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  0
 15 16  1  0
  5  7  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  2  0
  3  4  1  0
 18 19  2  0
  4  5  1  0
 25 26  2  0
 16 25  1  0
 21 22  1  0
 17 18  1  0
 13 14  1  6
 18 20  1  0
  5  6  1  6
 20 21  2  0
 13  2  1  0
  3  2  1  0
 21 25  1  0
  7  8  1  0
  5 12  1  0
  2  1  2  3
 12 13  1  0
 12 43  1  1
 16 17  2  0
 22 23  1  0
 23 24  1  0
  3 17  1  0
 15 47  1  0
 15 48  1  0
  3 29  1  1
  4 30  1  0
  4 31  1  0
 20 49  1  0
 11 41  1  0
 11 42  1  0
 10 39  1  0
 10 40  1  0
  9 38  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
  1 27  1  0
  1 28  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.918  -1.484  -0.506  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.598  -1.233  -0.529  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.657  -1.803   0.511  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.286  -2.832  -0.163  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.513  -2.641  -1.702  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.566  -3.402  -2.517  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.861  -3.252  -2.141  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.252  -4.604  -1.594  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -2.632  -3.026  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.370  -1.319  -3.683  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.954  -0.796  -3.435  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.496  -1.098  -1.998  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.835  -0.355  -1.531  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.704   0.113  -2.715  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.422   0.909  -0.703  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.189   0.570   0.648  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.102  -0.664   1.183  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.711  -0.956   2.500  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.635  -2.061   3.024  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.434   0.131   3.174  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.554   1.357   2.658  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.252   2.304   3.397  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.017   3.245   2.641  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.108   3.792   3.546  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.900   1.676   1.347  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.933   2.796   0.848  0.00  0.00           O+0
HETATM   27  H   UNK     0      -3.607  -1.078  -1.239  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.358  -2.118   0.260  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.237  -2.322   1.285  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.119  -3.838   0.016  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.253  -2.811   0.358  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.334  -3.407  -3.589  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.637  -4.450  -2.204  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.567  -2.982  -2.419  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.157  -4.994  -2.074  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.459  -5.339  -1.763  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.455  -4.549  -0.521  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.609  -3.094  -3.314  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.096  -0.585  -3.311  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.535  -1.406  -4.763  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.267  -1.242  -4.163  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.959   0.285  -3.621  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.312  -0.688  -1.381  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.609   0.629  -2.374  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.017  -0.730  -3.341  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.175   0.830  -3.350  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.299   1.546  -0.525  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.287   1.502  -1.295  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.878  -0.119   4.131  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.482   2.768   1.770  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.374   4.071   2.322  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.755   2.983   3.901  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.720   4.528   3.017  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.673   4.264   4.432  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2   13    3    1                                                  
CONECT    3    4    2   17   29                                             
CONECT    4    3    5   30   31                                             
CONECT    5    7    4    6   12                                             
CONECT    6    5   32   33   34                                             
CONECT    7    5    9    8                                                  
CONECT    8    7   35   36   37                                             
CONECT    9   10    7   38                                                  
CONECT   10   11    9   39   40                                             
CONECT   11   12   10   41   42                                             
CONECT   12   11    5   13   43                                             
CONECT   13   15   14    2   12                                             
CONECT   14   13   44   45   46                                             
CONECT   15   13   16   47   48                                             
CONECT   16   15   25   17                                                  
CONECT   17   18   16    3                                                  
CONECT   18   19   17   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   49                                                  
CONECT   21   22   20   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   50   51                                             
CONECT   24   23   52   53   54                                             
CONECT   25   26   16   21                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   20                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
   -2.9185   -1.4835   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980   -1.2326   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565   -1.8030    0.5109 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2864   -2.8323   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5125   -2.6411   -1.7021 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5657   -3.4022   -2.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8614   -3.2524   -2.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520   -4.6045   -1.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -2.6320   -3.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3699   -1.3189   -3.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537   -0.7956   -3.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -1.0984   -1.9981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8350   -0.3553   -1.5309 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7042    0.1126   -2.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4220    0.9085   -0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    0.5701    0.6484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015   -0.6641    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7112   -0.9563    2.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -2.0610    3.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    0.1314    3.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5543    1.3575    2.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    2.3041    3.3972 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0173    3.2447    2.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1077    3.7916    3.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9003    1.6755    1.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325    2.7958    0.8483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6068   -1.0783   -1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3579   -2.1181    0.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -2.3225    1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -3.8381    0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2528   -2.8114    0.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3341   -3.4071   -3.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369   -4.4502   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -2.9816   -2.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -4.9935   -2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4594   -5.3390   -1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553   -4.5493   -0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6094   -3.0935   -3.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -0.5854   -3.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5348   -1.4059   -4.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668   -1.2422   -4.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9591    0.2846   -3.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3120   -0.6882   -1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092    0.6289   -2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0174   -0.7298   -3.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1749    0.8304   -3.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2991    1.5460   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2873    1.5016   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8779   -0.1192    4.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4817    2.7683    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3740    4.0708    2.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550    2.9828    3.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7197    4.5278    3.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726    4.2643    4.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  0
 15 16  1  0
  5  7  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  2  0
  3  4  1  0
 18 19  2  0
  4  5  1  0
 25 26  2  0
 16 25  1  0
 21 22  1  0
 17 18  1  0
 13 14  1  6
 18 20  1  0
  5  6  1  6
 20 21  2  0
 13  2  1  0
  3  2  1  0
 21 25  1  0
  7  8  1  0
  5 12  1  0
  2  1  2  3
 12 13  1  0
 12 43  1  1
 16 17  2  0
 22 23  1  0
 23 24  1  0
  3 17  1  0
 15 47  1  0
 15 48  1  0
  3 29  1  1
  4 30  1  0
  4 31  1  0
 20 49  1  0
 11 41  1  0
 11 42  1  0
 10 39  1  0
 10 40  1  0
  9 38  1  0
 14 44  1  0
 14 45  1  0
 14 46  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  8 35  1  0
  8 36  1  0
  8 37  1  0
  1 27  1  0
  1 28  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₃

Average Mass

352.4740 Da

Monoisotopic Mass

352.20384 Da

IUPAC Name

(1R,9S,10R,15S)-5-ethoxy-9,14,15-trimethyl-17-methylidenetetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2(7),4,13-triene-3,6-dione

Traditional Name

(1R,9S,10R,15S)-5-ethoxy-9,14,15-trimethyl-17-methylidenetetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadeca-2(7),4,13-triene-3,6-dione

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1[C@]2([H])C3=C(C(=O)C(OC([H])([H])C([H])([H])[H])=C([H])C3=O)C([H])([H])[C@@]1(C([H])([H])[H])[C@]1([H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])[C@@]1(C([H])([H])[H])C2([H])[H]

InChI Identifier

InChI=1S/C23H28O3/c1-6-26-18-10-17(24)20-15-11-22(4)13(2)8-7-9-19(22)23(5,14(15)3)12-16(20)21(18)25/h8,10,15,19H,3,6-7,9,11-12H2,1-2,4-5H3/t15-,19-,22-,23-/m1/s1

InChI Key

OMLKNXFIVARPQF-BHAGSQDASA-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
Dysidea avara	JEOL database	Jiao, W.-H., et al, Org. Lett. 14, 202 (2012)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous esters. These are organic compounds containing an ester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous esters

Sub Class

Not Available

Direct Parent

Vinylogous esters

Alternative Parents

Substituents

Vinylogous ester
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	4.7	ALOGPS
logP	4.17	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.68 m³·mol⁻¹	ChemAxon
Polarizability	40.07 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

29212424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56964571

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
Fukui Y, Narita K, Katoh T: Enantioselective total synthesis of dysidavarone A, a novel sesquiterpenoid quinone from the marine sponge Dysidea avara. Chemistry. 2014 Feb 24;20(9):2436-9. doi: 10.1002/chem.201304809. Epub 2014 Jan 30. [PubMed:24482283 ]
Schmalzbauer B, Herrmann J, Muller R, Menche D: Total synthesis and antibacterial activity of dysidavarone A. Org Lett. 2013 Feb 15;15(4):964-7. doi: 10.1021/ol400156u. Epub 2013 Feb 7. [PubMed:23391209 ]
Jiao, W.-H., et al. (2012). Jiao, W.-H., et al, Org. Lett. 14, 202 (2012). Org. Lett..

Showing NP-Card for dysidavarone A (NP0041432)

MOL for NP0041432 (dysidavarone A)

3D MOL for NP0041432 (dysidavarone A)

3D SDF for NP0041432 (dysidavarone A)

3D-SDF for NP0041432 (dysidavarone A)

PDB for NP0041432 (dysidavarone A)

3D PDB for NP0041432 (dysidavarone A)

SMILES for NP0041432 (dysidavarone A)

INCHI for NP0041432 (dysidavarone A)

Structure for NP0041432 (dysidavarone A)

3D Structure for NP0041432 (dysidavarone A)