NP-MRD: Showing NP-Card for pycnanthuquinone C (NP0032892)

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Record Information

Version

1.0

Created at

2021-06-19 23:35:20 UTC

Updated at

2021-06-30 00:02:21 UTC

NP-MRD ID

NP0032892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pycnanthuquinone C

Provided By

JEOL Database JEOL Logo

Description

(?)-Pycnanthuquinone C belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). pycnanthuquinone C is found in Cystophora harveyi. It was first documented in 2007 (PMID: 17346075). Based on a literature review a small amount of articles have been published on (?)-Pycnanthuquinone C (PMID: 20645370) (PMID: 17295184).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101353D          

 43 45  0  0  0  0            999 V2000
   -0.2389   -0.7949    4.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1145    3.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2649    1.4242    3.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5367    2.3082    2.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662    3.5075    2.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6123    1.7029    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    0.3828    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705   -0.4954    1.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -1.7008    1.7227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937   -0.3498   -0.6176 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4011   -1.2492   -0.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2989    0.6111   -1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3188    1.7326   -1.5850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4527    2.3868   -2.9724 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9048    1.3613   -3.9831 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7065    0.0669   -3.1847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3247   -0.8640   -3.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -0.6102   -3.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    2.6240   -0.3540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2383    3.5530   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    3.4959   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.5786    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418   -0.2549    5.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2190   -1.2695    4.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501    1.9145    4.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210   -0.9522   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -1.9242    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060    1.0495   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    1.2647   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    3.3248   -3.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5050    2.6092   -3.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5967    1.2381   -4.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    1.7287   -4.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -1.7847   -3.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109   -0.3933   -3.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193   -1.1656   -4.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.1097   -2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    4.1441    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.9929   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    4.2764   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    2.8906    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184    4.2931    0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    3.9953   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 12  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 13  1  0  0  0  0
 19 21  1  0  0  0  0
 12 10  1  0  0  0  0
 16 17  1  0  0  0  0
 12 13  1  0  0  0  0
 16 18  1  1  0  0  0
  4  6  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
 13 29  1  1  0  0  0
  7  6  2  0  0  0  0
 12 28  1  6  0  0  0
  3 25  1  0  0  0  0
 10 26  1  1  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 11 27  1  0  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 21 43  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 17 36  1  0  0  0  0
 18 37  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -0.2389   -0.7949    4.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1145    3.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2649    1.4242    3.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5367    2.3082    2.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662    3.5075    2.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6123    1.7029    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    0.3828    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705   -0.4954    1.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -1.7008    1.7227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937   -0.3498   -0.6176 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4011   -1.2492   -0.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2989    0.6111   -1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3188    1.7326   -1.5850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4527    2.3868   -2.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048    1.3613   -3.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7065    0.0669   -3.1847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3247   -0.8640   -3.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -0.6102   -3.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    2.6240   -0.3540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2383    3.5530   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    3.4959   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.5786    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418   -0.2549    5.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2190   -1.2695    4.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501    1.9145    4.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210   -0.9522   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -1.9242    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060    1.0495   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    1.2647   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    3.3248   -3.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5050    2.6092   -3.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5967    1.2381   -4.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    1.7287   -4.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -1.7847   -3.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109   -0.3933   -3.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193   -1.1656   -4.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.1097   -2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    4.1441    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.9929   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    4.2764   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    2.8906    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184    4.2931    0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    3.9953   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  2  8  1  0
  8  9  2  0
  3  4  1  0
  4  5  2  0
  7 10  1  0
 10 11  1  0
  6 19  1  0
 19 20  1  6
 19 13  1  0
 19 21  1  0
 12 10  1  0
 16 17  1  0
 12 13  1  0
 16 18  1  1
  4  6  1  0
  2  1  1  0
  7  8  1  0
 13 29  1  1
  7  6  2  0
 12 28  1  6
  3 25  1  0
 10 26  1  1
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 11 27  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END


  Mrv1652306202101353D          

 43 45  0  0  0  0            999 V2000
   -0.2389   -0.7949    4.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1145    3.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2649    1.4242    3.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5367    2.3082    2.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662    3.5075    2.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6123    1.7029    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    0.3828    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705   -0.4954    1.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -1.7008    1.7227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937   -0.3498   -0.6176 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4011   -1.2492   -0.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2989    0.6111   -1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3188    1.7326   -1.5850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4527    2.3868   -2.9724 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9048    1.3613   -3.9831 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7065    0.0669   -3.1847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3247   -0.8640   -3.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -0.6102   -3.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    2.6240   -0.3540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2383    3.5530   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    3.4959   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.5786    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418   -0.2549    5.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2190   -1.2695    4.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501    1.9145    4.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210   -0.9522   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -1.9242    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060    1.0495   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    1.2647   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    3.3248   -3.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5050    2.6092   -3.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5967    1.2381   -4.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    1.7287   -4.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -1.7847   -3.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109   -0.3933   -3.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193   -1.1656   -4.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.1097   -2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    4.1441    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.9929   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    4.2764   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    2.8906    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184    4.2931    0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    3.9953   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 12  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 13  1  0  0  0  0
 19 21  1  0  0  0  0
 12 10  1  0  0  0  0
 16 17  1  0  0  0  0
 12 13  1  0  0  0  0
 16 18  1  1  0  0  0
  4  6  1  0  0  0  0
  2  1  1  0  0  0  0
  7  8  1  0  0  0  0
 13 29  1  1  0  0  0
  7  6  2  0  0  0  0
 12 28  1  6  0  0  0
  3 25  1  0  0  0  0
 10 26  1  1  0  0  0
 14 30  1  0  0  0  0
 14 31  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 11 27  1  0  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  0  0  0  0
 21 42  1  0  0  0  0
 21 43  1  0  0  0  0
 17 34  1  0  0  0  0
 17 35  1  0  0  0  0
 17 36  1  0  0  0  0
 18 37  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C2=C(C(=O)C([H])=C(C2=O)C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@](O[H])(C([H])([H])[H])[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-8-7-10(18)13-11(14(8)19)15(20)12-9(16(13,2)3)5-6-17(12,4)21/h7,9,12,15,20-21H,5-6H2,1-4H3/t9-,12-,15+,17-/m1/s1

> <INCHI_KEY>
TZRVFRBFVXPYHU-YVZBYOTBSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.359

> <EXACT_MASS>
290.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.4223999587473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3aR,9R,9aR)-1,9-dihydroxy-1,4,4,7-tetramethyl-1H,2H,3H,3aH,4H,5H,8H,9H,9aH-cyclopenta[b]naphthalene-5,8-dione

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.5606814093333337

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.864123241266793

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.909422707112906

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9358278220432785

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
80.06700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3aR,9R,9aR)-1,9-dihydroxy-1,4,4,7-tetramethyl-2H,3H,3aH,9H,9aH-cyclopenta[b]naphthalene-5,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -0.2389   -0.7949    4.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1145    3.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2649    1.4242    3.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5367    2.3082    2.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662    3.5075    2.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6123    1.7029    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    0.3828    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705   -0.4954    1.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -1.7008    1.7227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937   -0.3498   -0.6176 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4011   -1.2492   -0.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2989    0.6111   -1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3188    1.7326   -1.5850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4527    2.3868   -2.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048    1.3613   -3.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7065    0.0669   -3.1847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3247   -0.8640   -3.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -0.6102   -3.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    2.6240   -0.3540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2383    3.5530   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    3.4959   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.5786    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418   -0.2549    5.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2190   -1.2695    4.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501    1.9145    4.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210   -0.9522   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -1.9242    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060    1.0495   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    1.2647   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    3.3248   -3.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5050    2.6092   -3.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5967    1.2381   -4.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    1.7287   -4.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -1.7847   -3.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109   -0.3933   -3.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193   -1.1656   -4.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.1097   -2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    4.1441    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.9929   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    4.2764   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    2.8906    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184    4.2931    0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    3.9953   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  2  8  1  0
  8  9  2  0
  3  4  1  0
  4  5  2  0
  7 10  1  0
 10 11  1  0
  6 19  1  0
 19 20  1  6
 19 13  1  0
 19 21  1  0
 12 10  1  0
 16 17  1  0
 12 13  1  0
 16 18  1  1
  4  6  1  0
  2  1  1  0
  7  8  1  0
 13 29  1  1
  7  6  2  0
 12 28  1  6
  3 25  1  0
 10 26  1  1
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 11 27  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
  1 22  1  0
  1 23  1  0
  1 24  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      -0.239  -0.795   4.376  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.042   0.115   3.222  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.265   1.424   3.355  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.537   2.308   2.208  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.666   3.507   2.419  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.612   1.703   0.841  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.350   0.383   0.705  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.071  -0.495   1.876  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.106  -1.701   1.723  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.294  -0.350  -0.618  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.401  -1.249  -0.689  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.299   0.611  -1.806  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.319   1.733  -1.585  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.453   2.387  -2.972  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.905   1.361  -3.983  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.707   0.067  -3.185  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.325  -0.864  -3.802  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.962  -0.610  -3.161  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.964   2.624  -0.354  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.238   3.553  -0.630  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.212   3.496  -0.077  0.00  0.00           C+0
HETATM   22  H   UNK     0       0.523  -1.579   4.442  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.242  -0.255   5.329  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.219  -1.270   4.261  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.250   1.915   4.323  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.621  -0.952  -0.684  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.237  -1.924   0.004  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.706   1.050  -1.889  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.294   1.265  -1.372  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.903   3.325  -3.074  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.505   2.609  -3.183  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.597   1.238  -4.823  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.051   1.729  -4.377  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.419  -1.785  -3.216  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.311  -0.393  -3.867  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.019  -1.166  -4.811  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.004  -1.110  -2.317  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.506   4.144   0.252  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.133   2.993  -0.920  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.022   4.276  -1.422  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.043   2.891   0.304  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.018   4.293   0.647  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.557   3.995  -0.989  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    3    8    1                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6   19    4    7                                                  
CONECT    7   10    8    6                                                  
CONECT    8    2    9    7                                                  
CONECT    9    8                                                            
CONECT   10    7   11   12   26                                             
CONECT   11   10   27                                                       
CONECT   12   16   10   13   28                                             
CONECT   13   14   19   12   29                                             
CONECT   14   13   15   30   31                                             
CONECT   15   14   16   32   33                                             
CONECT   16   15   12   17   18                                             
CONECT   17   16   34   35   36                                             
CONECT   18   16   37                                                       
CONECT   19    6   20   13   21                                             
CONECT   20   19   38   39   40                                             
CONECT   21   19   41   42   43                                             
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26   10                                                            
CONECT   27   11                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   14                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   17                                                            
CONECT   35   17                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   20                                                            
CONECT   39   20                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   21                                                            
CONECT   43   21                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   90    0
END

RDKit          3D

43 45  0  0  0  0  0  0  0  0999 V2000
   -0.2389   -0.7949    4.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417    0.1145    3.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2649    1.4242    3.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5367    2.3082    2.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6662    3.5075    2.4191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6123    1.7029    0.8414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504    0.3828    0.7047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705   -0.4954    1.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1058   -1.7008    1.7227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937   -0.3498   -0.6176 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4011   -1.2492   -0.6892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2989    0.6111   -1.8060 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3188    1.7326   -1.5850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4527    2.3868   -2.9724 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048    1.3613   -3.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7065    0.0669   -3.1847 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3247   -0.8640   -3.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9619   -0.6102   -3.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9640    2.6240   -0.3540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2383    3.5530   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    3.4959   -0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.5786    4.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418   -0.2549    5.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2190   -1.2695    4.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2501    1.9145    4.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6210   -0.9522   -0.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -1.9242    0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7060    1.0495   -1.8893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2943    1.2647   -1.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    3.3248   -3.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5050    2.6092   -3.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5967    1.2381   -4.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0505    1.7287   -4.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4186   -1.7847   -3.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109   -0.3933   -3.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193   -1.1656   -4.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.1097   -2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5062    4.1441    0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1331    2.9929   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    4.2764   -1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427    2.8906    0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0184    4.2931    0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    3.9953   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  2  8  1  0
  8  9  2  0
  3  4  1  0
  4  5  2  0
  7 10  1  0
 10 11  1  0
  6 19  1  0
 19 20  1  6
 19 13  1  0
 19 21  1  0
 12 10  1  0
 16 17  1  0
 12 13  1  0
 16 18  1  1
  4  6  1  0
  2  1  1  0
  7  8  1  0
 13 29  1  1
  7  6  2  0
 12 28  1  6
  3 25  1  0
 10 26  1  1
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 11 27  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O₄

Average Mass

290.3590 Da

Monoisotopic Mass

290.15181 Da

IUPAC Name

(1R,3aR,9R,9aR)-1,9-dihydroxy-1,4,4,7-tetramethyl-1H,2H,3H,3aH,4H,5H,8H,9H,9aH-cyclopenta[b]naphthalene-5,8-dione

Traditional Name

(1R,3aR,9R,9aR)-1,9-dihydroxy-1,4,4,7-tetramethyl-2H,3H,3aH,9H,9aH-cyclopenta[b]naphthalene-5,8-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C2=C(C(=O)C([H])=C(C2=O)C([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@](O[H])(C([H])([H])[H])[C@@]12[H]

InChI Identifier

InChI=1S/C17H22O4/c1-8-7-10(18)13-11(14(8)19)15(20)12-9(16(13,2)3)5-6-17(12,4)21/h7,9,12,15,20-21H,5-6H2,1-4H3/t9-,12-,15+,17-/m1/s1

InChI Key

TZRVFRBFVXPYHU-YVZBYOTBSA-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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cystophora harveyi	JEOL database	Laird, D. W., et al, J. Nat. Prod. 70, 671 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
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	1.58	ALOGPS
logP	1.56	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.91	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.07 m³·mol⁻¹	ChemAxon
Polarizability	31.42 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	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

46944635

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lobermann F, Mayer P, Trauner D: Biomimetic synthesis of (-)-pycnanthuquinone C through the Diels-Alder reaction of a vinyl quinone. Angew Chem Int Ed Engl. 2010 Aug 16;49(35):6199-202. doi: 10.1002/anie.201001862. [PubMed:20645370 ]
Laird DW, Poole R, Wikstrom M, Altena IA: Pycnanthuquinone C, an unusual 6,6,5-tricyclic Geranyltoluquinone from the Western Australian brown alga Cystophora harveyi. J Nat Prod. 2007 Apr;70(4):671-4. doi: 10.1021/np060566m. Epub 2007 Mar 9. [PubMed:17346075 ]
Wabo HK, Tatsimo SN, Tane P, Connolly JD: Pycnanthuquinone C: a new terpenoid-quinone from Pycnanthus angolensis. Planta Med. 2007 Feb;73(2):187-9. doi: 10.1055/s-2007-967103. Epub 2007 Feb 13. [PubMed:17295184 ]
Laird, D. W., et al. (2007). Laird, D. W., et al, J. Nat. Prod. 70, 671 (2007) . J. Nat. Prod..

Showing NP-Card for pycnanthuquinone C (NP0032892)

MOL for NP0032892 (pycnanthuquinone C)

3D MOL for NP0032892 (pycnanthuquinone C)

3D SDF for NP0032892 (pycnanthuquinone C)

3D-SDF for NP0032892 (pycnanthuquinone C)

PDB for NP0032892 (pycnanthuquinone C)

3D PDB for NP0032892 (pycnanthuquinone C)

SMILES for NP0032892 (pycnanthuquinone C)

INCHI for NP0032892 (pycnanthuquinone C)

Structure for NP0032892 (pycnanthuquinone C)

3D Structure for NP0032892 (pycnanthuquinone C)