NP-MRD: Showing NP-Card for caucanolide C (NP0028663)

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Record Information

Version

2.0

Created at

2021-06-19 20:29:45 UTC

Updated at

2021-06-29 23:55:35 UTC

NP-MRD ID

NP0028663

Secondary Accession Numbers

None

Natural Product Identification

Common Name

caucanolide C

Provided By

JEOL Database JEOL Logo

Description

caucanolide C is found in Pseudopterogorgia bipinnata. caucanolide C was first documented in 2005 (Ospina, C. A., et al.). Based on a literature review very few articles have been published on caucanolide C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122293D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192122293D          

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   -0.5317   -3.4142    3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -3.9115    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6572   -5.1976    1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0126   -3.5009    1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7689   -4.8512    3.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -3.1545    3.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737   -4.4756    3.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927    3.0111   -1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    3.6098    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    3.2545    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351    0.4541    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952    2.0920    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309    1.8288    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190    0.3184    1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2071    1.8845    2.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9018    3.2611    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085    3.4625    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 26  1  0  0  0  0
  4 20  1  0  0  0  0
 19 20  1  0  0  0  0
  3  2  1  6  0  0  0
 26 24  1  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 11 12  1  0  0  0  0
 24 23  2  0  0  0  0
 12 13  2  0  0  0  0
 23  3  1  0  0  0  0
 12 40  1  0  0  0  0
  8  7  2  0  0  0  0
 11 14  2  3  0  0  0
  3 28  1  0  0  0  0
 14 15  1  0  0  0  0
  7  5  1  0  0  0  0
 14 16  1  0  0  0  0
 24 25  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
  4  3  1  0  0  0  0
  4 32  1  6  0  0  0
  5  4  1  0  0  0  0
 20 21  1  6  0  0  0
 26 27  2  0  0  0  0
 20 22  1  0  0  0  0
 17 19  1  0  0  0  0
  5  6  1  0  0  0  0
 23 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  7 35  1  0  0  0  0
  5 33  1  6  0  0  0
 10 38  1  0  0  0  0
 10 39  1  0  0  0  0
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 21 49  1  0  0  0  0
 22 50  1  0  0  0  0
 22 51  1  0  0  0  0
 22 52  1  0  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028663

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O7/c1-12(2)15(11-22)8-7-14-9-16(23)17(20(4,5)27-19(14)25)21(26-6)10-13(3)18(24)28-21/h9-11,16-17,23H,7-8H2,1-6H3/t16-,17-,21-/m0/s1

> <INCHI_KEY>
DRGJVXACADCLMU-FIKGOQFSSA-N

> <FORMULA>
C21H28O7

> <MOLECULAR_WEIGHT>
392.448

> <EXACT_MASS>
392.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.81581718636248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{2-[(5S,6S)-5-hydroxy-6-[(2S)-2-methoxy-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]-7,7-dimethyl-2-oxo-2,5,6,7-tetrahydrooxepin-3-yl]ethyl}-3-methylbut-2-enal

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
3.315850044333334

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.229539014326278

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1357996351336848

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
103.58199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{2-[(5S,6S)-5-hydroxy-6-[(2S)-2-methoxy-4-methyl-5-oxofuran-2-yl]-7,7-dimethyl-2-oxo-5,6-dihydrooxepin-3-yl]ethyl}-3-methylbut-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
    3.6934    1.2753   -2.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    0.7821   -1.6457 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812    1.4096   -0.6690 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5423    0.7910   -0.7258 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6316   -0.7573   -0.6085 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9066   -1.1598    0.7282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356   -1.5322   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -1.4416   -0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -2.4131   -0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212   -3.8055   -0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000   -3.8219    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4907   -3.5851    1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5863   -3.5540    1.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9344   -4.0265    1.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -4.1688    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0040   -4.1252    3.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -0.3919    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141   -0.5852    1.4421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8518    0.8210   -0.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297    1.4505    0.1727 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1600    2.9143   -0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6604    1.4522    1.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229    1.2687    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640    2.4417    1.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9623    2.7793    2.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6970    3.4400    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    4.6378    0.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599    2.8249   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3230    0.6651   -3.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    1.1985   -3.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0426    2.3096   -3.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1886    0.9605   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721   -1.1206   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -2.0985    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6568   -2.3278   -1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8834   -1.9989   -0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592   -2.5304   -2.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -4.2417   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4760   -4.4820   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5317   -3.4142    3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -3.9115    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6572   -5.1976    1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0126   -3.5009    1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7689   -4.8512    3.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -3.1545    3.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737   -4.4756    3.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927    3.0111   -1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    3.6098    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    3.2545    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351    0.4541    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952    2.0920    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309    1.8288    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190    0.3184    1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2071    1.8845    2.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9018    3.2611    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085    3.4625    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 26  1  0
  4 20  1  0
 19 20  1  0
  3  2  1  6
 26 24  1  0
 10 11  1  0
  2  1  1  0
 11 12  1  0
 24 23  2  0
 12 13  2  0
 23  3  1  0
 12 40  1  0
  8  7  2  0
 11 14  2  3
  3 28  1  0
 14 15  1  0
  7  5  1  0
 14 16  1  0
 24 25  1  0
 10  9  1  0
  9  8  1  0
  8 17  1  0
 17 18  2  0
  4  3  1  0
  4 32  1  6
  5  4  1  0
 20 21  1  6
 26 27  2  0
 20 22  1  0
 17 19  1  0
  5  6  1  0
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 35  1  0
  5 33  1  6
 10 38  1  0
 10 39  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
  9 36  1  0
  9 37  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
  6 34  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.693   1.275  -2.971  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.834   0.782  -1.646  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.981   1.410  -0.669  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.542   0.791  -0.726  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.632  -0.757  -0.609  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.907  -1.160   0.728  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.436  -1.532  -1.089  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.812  -1.442  -0.596  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.910  -2.413  -0.923  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.721  -3.805  -0.292  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.800  -3.822   1.222  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.491  -3.585   1.917  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.586  -3.554   1.325  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.934  -4.027   1.936  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.298  -4.169   1.299  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.004  -4.125   3.442  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.119  -0.392   0.396  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.714  -0.585   1.442  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.852   0.821  -0.136  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.430   1.450   0.173  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.160   2.914  -0.241  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.660   1.452   1.693  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.723   1.269   0.608  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.164   2.442   1.056  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.962   2.779   2.251  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.697   3.440   0.096  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.902   4.638   0.164  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.960   2.825  -0.868  0.00  0.00           O+0
HETATM   29  H   UNK     0       4.323   0.665  -3.625  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.663   1.198  -3.325  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.043   2.310  -3.040  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.189   0.961  -1.754  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.472  -1.121  -1.210  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.632  -2.099   0.839  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.657  -2.328  -1.798  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.883  -1.999  -0.630  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.959  -2.530  -2.013  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.770  -4.242  -0.625  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.476  -4.482  -0.712  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.532  -3.414   3.002  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.319  -3.912   0.238  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.657  -5.198   1.406  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.013  -3.501   1.794  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.769  -4.851   3.741  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.270  -3.155   3.872  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.074  -4.476   3.896  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.093   3.011  -1.330  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.915   3.610   0.131  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.807   3.255   0.153  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.835   0.454   2.099  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.495   2.092   1.986  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.231   1.829   2.211  0.00  0.00           H+0
HETATM   53  H   UNK     0       3.919   0.318   1.084  0.00  0.00           H+0
HETATM   54  H   UNK     0       5.207   1.885   2.832  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.902   3.261   1.963  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.409   3.462   2.902  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    2   23   28    4                                             
CONECT    4   20    3   32    5                                             
CONECT    5    7    4    6   33                                             
CONECT    6    5   34                                                       
CONECT    7    8    5   35                                                  
CONECT    8    7    9   17                                                  
CONECT    9   10    8   36   37                                             
CONECT   10   11    9   38   39                                             
CONECT   11   10   12   14                                                  
CONECT   12   11   13   40                                                  
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14   41   42   43                                             
CONECT   16   14   44   45   46                                             
CONECT   17    8   18   19                                                  
CONECT   18   17                                                            
CONECT   19   20   17                                                       
CONECT   20    4   19   21   22                                             
CONECT   21   20   47   48   49                                             
CONECT   22   20   50   51   52                                             
CONECT   23   24    3   53                                                  
CONECT   24   26   23   25                                                  
CONECT   25   24   54   55   56                                             
CONECT   26   28   24   27                                                  
CONECT   27   26                                                            
CONECT   28   26    3                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   12                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   21                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  114    0
END

RDKit          3D

56 57  0  0  0  0  0  0  0  0999 V2000
    3.6934    1.2753   -2.9714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    0.7821   -1.6457 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812    1.4096   -0.6690 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5423    0.7910   -0.7258 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6316   -0.7573   -0.6085 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9066   -1.1598    0.7282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4356   -1.5322   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8120   -1.4416   -0.5956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -2.4131   -0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7212   -3.8055   -0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000   -3.8219    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4907   -3.5851    1.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5863   -3.5540    1.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9344   -4.0265    1.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2981   -4.1688    1.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0040   -4.1252    3.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1188   -0.3919    0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141   -0.5852    1.4421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8518    0.8210   -0.1356 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4297    1.4505    0.1727 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1600    2.9143   -0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6604    1.4522    1.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7229    1.2687    0.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640    2.4417    1.0557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9623    2.7793    2.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6970    3.4400    0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    4.6378    0.1639 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599    2.8249   -0.8681 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3230    0.6651   -3.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    1.1985   -3.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0426    2.3096   -3.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1886    0.9605   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4721   -1.1206   -1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6324   -2.0985    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6568   -2.3278   -1.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8834   -1.9989   -0.6296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592   -2.5304   -2.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -4.2417   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4760   -4.4820   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5317   -3.4142    3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -3.9115    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6572   -5.1976    1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0126   -3.5009    1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7689   -4.8512    3.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2697   -3.1545    3.8723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0737   -4.4756    3.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0927    3.0111   -1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151    3.6098    0.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065    3.2545    0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351    0.4541    2.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4952    2.0920    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2309    1.8288    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190    0.3184    1.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2071    1.8845    2.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9018    3.2611    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4085    3.4625    2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 26  1  0
  4 20  1  0
 19 20  1  0
  3  2  1  6
 26 24  1  0
 10 11  1  0
  2  1  1  0
 11 12  1  0
 24 23  2  0
 12 13  2  0
 23  3  1  0
 12 40  1  0
  8  7  2  0
 11 14  2  3
  3 28  1  0
 14 15  1  0
  7  5  1  0
 14 16  1  0
 24 25  1  0
 10  9  1  0
  9  8  1  0
  8 17  1  0
 17 18  2  0
  4  3  1  0
  4 32  1  6
  5  4  1  0
 20 21  1  6
 26 27  2  0
 20 22  1  0
 17 19  1  0
  5  6  1  0
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 35  1  0
  5 33  1  6
 10 38  1  0
 10 39  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
  9 36  1  0
  9 37  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
  6 34  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₇

Average Mass

392.4480 Da

Monoisotopic Mass

392.18350 Da

IUPAC Name

2-{2-[(5S,6S)-5-hydroxy-6-[(2S)-2-methoxy-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]-7,7-dimethyl-2-oxo-2,5,6,7-tetrahydrooxepin-3-yl]ethyl}-3-methylbut-2-enal

Traditional Name

2-{2-[(5S,6S)-5-hydroxy-6-[(2S)-2-methoxy-4-methyl-5-oxofuran-2-yl]-7,7-dimethyl-2-oxo-5,6-dihydrooxepin-3-yl]ethyl}-3-methylbut-2-enal

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H28O7/c1-12(2)15(11-22)8-7-14-9-16(23)17(20(4,5)27-19(14)25)21(26-6)10-13(3)18(24)28-21/h9-11,16-17,23H,7-8H2,1-6H3/t16-,17-,21-/m0/s1

InChI Key

DRGJVXACADCLMU-FIKGOQFSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Antillogorgia bipinnata	JEOL database	Ospina, C. A., et al, J. Nat. Prod. 68, 1519 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
2-furanone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated aldehyde
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enal
Dihydrofuran
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Aldehyde
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.27	ALOGPS
logP	3.32	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.23	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.58 m³·mol⁻¹	ChemAxon
Polarizability	40.82 Å³	ChemAxon
Number of Rings	2	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

9814488

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11639746

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ospina, C. A., et al. (2005). Ospina, C. A., et al, J. Nat. Prod. 68, 1519 (2005). J. Nat. Prod..

Showing NP-Card for caucanolide C (NP0028663)

MOL for NP0028663 (caucanolide C)

3D MOL for NP0028663 (caucanolide C)

3D SDF for NP0028663 (caucanolide C)

3D-SDF for NP0028663 (caucanolide C)

PDB for NP0028663 (caucanolide C)

3D PDB for NP0028663 (caucanolide C)

SMILES for NP0028663 (caucanolide C)

INCHI for NP0028663 (caucanolide C)

Structure for NP0028663 (caucanolide C)

3D Structure for NP0028663 (caucanolide C)