NP-MRD: Showing NP-Card for Pachyclavulariolide K (NP0025395)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 17:32:03 UTC

Updated at

2021-06-29 23:50:19 UTC

NP-MRD ID

NP0025395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pachyclavulariolide K

Provided By

JEOL Database JEOL Logo

Description

(1S,2R,3S,8R,14S,15R)-3-(acetyloxy)-8-hydroxy-1,5,14-trimethyl-10-methylidene-6,11-dioxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]Octadec-4-en-2-yl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Pachyclavulariolide K is found in Pachyclavularia violacea. Pachyclavulariolide K was first documented in 2001 (Sheu, J.-H., et al.). Based on a literature review very few articles have been published on (1S,2R,3S,8R,14S,15R)-3-(acetyloxy)-8-hydroxy-1,5,14-trimethyl-10-methylidene-6,11-dioxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]Octadec-4-en-2-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119323D          

 65 67  0  0  0  0            999 V2000
    1.0535   -3.9807   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824   -2.6710   -1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.5878   -0.2791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6029   -0.8640    0.7730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7187   -0.6423    0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722   -1.6383    1.9653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692   -0.9410    2.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -1.3712    4.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.4054    2.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0925    1.4010    3.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487    0.4568    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251    1.5827    0.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3271    2.4673    0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    2.0442    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905    3.0675    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024    0.9833   -0.4346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    2.4139    0.0898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0563    3.5631    0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    3.4082    2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    4.6801    2.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    2.3912    2.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    2.9207   -1.3670 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7685    3.8337   -1.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    3.6272   -1.4906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6386    2.4968   -1.8506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7670    1.6453   -2.7634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4295    1.7693   -2.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100    0.1683   -2.8595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6397    0.0766   -3.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -0.6887   -3.7475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0176   -1.2207   -3.0442 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3183   -2.2802   -1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099   -2.8395   -1.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986   -4.7258   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237   -4.3470   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646   -2.0145    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010   -0.8865   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557   -1.5149    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    1.4597    4.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1143    1.1188    3.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    2.4061    2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    1.1432   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725    2.7315    0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6235    3.1892    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576    4.0175   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9470    1.7760    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867    4.9241    3.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    4.5497    3.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    5.4890    2.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8982    4.7164   -1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526    4.1727   -2.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    3.3021   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162    4.1642   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    4.3519   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    2.8461   -2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229    1.9444   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523    2.0889   -3.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -0.2587   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063    0.5165   -4.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9654   -0.9673   -3.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535    0.5931   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -0.0996   -4.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.5503   -4.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -1.6959   -3.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -0.3977   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0  0  0  0
 26 27  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24 22  1  0  0  0  0
 30 28  1  0  0  0  0
 26 28  1  0  0  0  0
 11  9  2  0  0  0  0
  7  8  2  0  0  0  0
  9  7  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
 28 29  1  0  0  0  0
  4  6  1  0  0  0  0
 22 23  1  6  0  0  0
  2  3  1  0  0  0  0
 17 18  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  0  0  0  0
  4  3  1  0  0  0  0
 13 14  1  0  0  0  0
 22 17  1  0  0  0  0
 14 15  1  0  0  0  0
 17 12  1  0  0  0  0
 18 19  1  0  0  0  0
 22 27  1  0  0  0  0
 19 20  1  0  0  0  0
  4 11  1  0  0  0  0
 14 16  2  0  0  0  0
 32  2  1  0  0  0  0
 19 21  2  0  0  0  0
 31 30  1  0  0  0  0
  4  5  1  6  0  0  0
  2  1  2  3  0  0  0
 32 33  2  0  0  0  0
 31 64  1  0  0  0  0
 31 65  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
 17 46  1  1  0  0  0
 12 42  1  6  0  0  0
 26 57  1  6  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 24 53  1  0  0  0  0
 24 54  1  0  0  0  0
 28 58  1  1  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 29 59  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 23 52  1  0  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
  5 38  1  0  0  0  0
M  END

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
    1.0535   -3.9807   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824   -2.6710   -1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.5878   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6029   -0.8640    0.7730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7187   -0.6423    0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722   -1.6383    1.9653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692   -0.9410    2.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -1.3712    4.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.4054    2.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0925    1.4010    3.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487    0.4568    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251    1.5827    0.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3271    2.4673    0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    2.0442    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905    3.0675    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024    0.9833   -0.4346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    2.4139    0.0898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0563    3.5631    0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    3.4082    2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    4.6801    2.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    2.3912    2.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    2.9207   -1.3670 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7685    3.8337   -1.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    3.6272   -1.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386    2.4968   -1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670    1.6453   -2.7634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4295    1.7693   -2.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100    0.1683   -2.8595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6397    0.0766   -3.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -0.6887   -3.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176   -1.2207   -3.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -2.2802   -1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099   -2.8395   -1.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986   -4.7258   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237   -4.3470   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646   -2.0145    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010   -0.8865   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557   -1.5149    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    1.4597    4.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1143    1.1188    3.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    2.4061    2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    1.1432   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725    2.7315    0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6235    3.1892    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576    4.0175   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9470    1.7760    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867    4.9241    3.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    4.5497    3.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    5.4890    2.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8982    4.7164   -1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526    4.1727   -2.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    3.3021   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162    4.1642   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    4.3519   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    2.8461   -2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229    1.9444   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523    2.0889   -3.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -0.2587   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063    0.5165   -4.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9654   -0.9673   -3.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535    0.5931   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -0.0996   -4.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.5503   -4.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -1.6959   -3.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -0.3977   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 26 27  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 30 28  1  0
 26 28  1  0
 11  9  2  0
  7  8  2  0
  9  7  1  0
  9 10  1  0
  7  6  1  0
 28 29  1  0
  4  6  1  0
 22 23  1  6
  2  3  1  0
 17 18  1  0
 12 11  1  0
 12 13  1  0
  4  3  1  0
 13 14  1  0
 22 17  1  0
 14 15  1  0
 17 12  1  0
 18 19  1  0
 22 27  1  0
 19 20  1  0
  4 11  1  0
 14 16  2  0
 32  2  1  0
 19 21  2  0
 31 30  1  0
  4  5  1  6
  2  1  2  3
 32 33  2  0
 31 64  1  0
 31 65  1  0
 30 62  1  0
 30 63  1  0
  3 36  1  0
  3 37  1  0
  1 34  1  0
  1 35  1  0
 17 46  1  1
 12 42  1  6
 26 57  1  6
 25 55  1  0
 25 56  1  0
 24 53  1  0
 24 54  1  0
 28 58  1  1
 10 39  1  0
 10 40  1  0
 10 41  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
  5 38  1  0
M  END


  Mrv1652306192119323D          

 65 67  0  0  0  0            999 V2000
    1.0535   -3.9807   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824   -2.6710   -1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.5878   -0.2791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6029   -0.8640    0.7730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7187   -0.6423    0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722   -1.6383    1.9653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692   -0.9410    2.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -1.3712    4.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.4054    2.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0925    1.4010    3.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487    0.4568    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251    1.5827    0.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3271    2.4673    0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    2.0442    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905    3.0675    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024    0.9833   -0.4346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    2.4139    0.0898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0563    3.5631    0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    3.4082    2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    4.6801    2.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    2.3912    2.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    2.9207   -1.3670 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7685    3.8337   -1.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    3.6272   -1.4906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6386    2.4968   -1.8506 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7670    1.6453   -2.7634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4295    1.7693   -2.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100    0.1683   -2.8595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6397    0.0766   -3.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -0.6887   -3.7475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0176   -1.2207   -3.0442 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3183   -2.2802   -1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099   -2.8395   -1.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986   -4.7258   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237   -4.3470   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646   -2.0145    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010   -0.8865   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557   -1.5149    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    1.4597    4.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1143    1.1188    3.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    2.4061    2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    1.1432   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725    2.7315    0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6235    3.1892    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576    4.0175   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9470    1.7760    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867    4.9241    3.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    4.5497    3.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    5.4890    2.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8982    4.7164   -1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526    4.1727   -2.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    3.3021   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162    4.1642   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    4.3519   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    2.8461   -2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229    1.9444   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523    2.0889   -3.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -0.2587   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063    0.5165   -4.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9654   -0.9673   -3.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535    0.5931   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -0.0996   -4.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.5503   -4.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -1.6959   -3.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -0.3977   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0  0  0  0
 26 27  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  1  0  0  0  0
 24 22  1  0  0  0  0
 30 28  1  0  0  0  0
 26 28  1  0  0  0  0
 11  9  2  0  0  0  0
  7  8  2  0  0  0  0
  9  7  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
 28 29  1  0  0  0  0
  4  6  1  0  0  0  0
 22 23  1  6  0  0  0
  2  3  1  0  0  0  0
 17 18  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  0  0  0  0
  4  3  1  0  0  0  0
 13 14  1  0  0  0  0
 22 17  1  0  0  0  0
 14 15  1  0  0  0  0
 17 12  1  0  0  0  0
 18 19  1  0  0  0  0
 22 27  1  0  0  0  0
 19 20  1  0  0  0  0
  4 11  1  0  0  0  0
 14 16  2  0  0  0  0
 32  2  1  0  0  0  0
 19 21  2  0  0  0  0
 31 30  1  0  0  0  0
  4  5  1  6  0  0  0
  2  1  2  3  0  0  0
 32 33  2  0  0  0  0
 31 64  1  0  0  0  0
 31 65  1  0  0  0  0
 30 62  1  0  0  0  0
 30 63  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
 17 46  1  1  0  0  0
 12 42  1  6  0  0  0
 26 57  1  6  0  0  0
 25 55  1  0  0  0  0
 25 56  1  0  0  0  0
 24 53  1  0  0  0  0
 24 54  1  0  0  0  0
 28 58  1  1  0  0  0
 10 39  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 29 59  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 23 50  1  0  0  0  0
 23 51  1  0  0  0  0
 23 52  1  0  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
  5 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025395

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12OC(=O)C(=C1[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]1(O[C@]([H])(C([H])([H])C1([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C(=O)C(=C([H])[H])C2([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O9/c1-12-7-8-17(27)13(2)11-24(29)19(14(3)22(28)33-24)20(30-15(4)25)21(31-16(5)26)23(6)10-9-18(12)32-23/h12,18,20-21,29H,2,7-11H2,1,3-6H3/t12-,18+,20-,21+,23-,24+/m0/s1

> <INCHI_KEY>
SRKPHIQXGQJUBL-UVVXZCJPSA-N

> <FORMULA>
C24H32O9

> <MOLECULAR_WEIGHT>
464.511

> <EXACT_MASS>
464.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.2028176801816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3S,8R,14S,15R)-3-(acetyloxy)-8-hydroxy-1,5,14-trimethyl-10-methylidene-6,11-dioxo-7,18-dioxatricyclo[13.2.1.0^{4,8}]octadec-4-en-2-yl acetate

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
2.4278883476666655

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.099661569979963

> <JCHEM_PKA_STRONGEST_BASIC>
-4.171996806960155

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000004

> <JCHEM_REFRACTIVITY>
114.84379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,8R,14S,15R)-3-(acetyloxy)-8-hydroxy-1,5,14-trimethyl-10-methylidene-6,11-dioxo-7,18-dioxatricyclo[13.2.1.0^{4,8}]octadec-4-en-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
    1.0535   -3.9807   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824   -2.6710   -1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.5878   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6029   -0.8640    0.7730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7187   -0.6423    0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722   -1.6383    1.9653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692   -0.9410    2.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -1.3712    4.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.4054    2.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0925    1.4010    3.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487    0.4568    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251    1.5827    0.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3271    2.4673    0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    2.0442    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905    3.0675    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024    0.9833   -0.4346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    2.4139    0.0898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0563    3.5631    0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    3.4082    2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    4.6801    2.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    2.3912    2.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    2.9207   -1.3670 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7685    3.8337   -1.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    3.6272   -1.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386    2.4968   -1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670    1.6453   -2.7634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4295    1.7693   -2.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100    0.1683   -2.8595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6397    0.0766   -3.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -0.6887   -3.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176   -1.2207   -3.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -2.2802   -1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099   -2.8395   -1.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986   -4.7258   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237   -4.3470   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646   -2.0145    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010   -0.8865   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557   -1.5149    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    1.4597    4.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1143    1.1188    3.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    2.4061    2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    1.1432   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725    2.7315    0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6235    3.1892    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576    4.0175   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9470    1.7760    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867    4.9241    3.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    4.5497    3.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    5.4890    2.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8982    4.7164   -1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526    4.1727   -2.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    3.3021   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162    4.1642   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    4.3519   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    2.8461   -2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229    1.9444   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523    2.0889   -3.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -0.2587   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063    0.5165   -4.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9654   -0.9673   -3.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535    0.5931   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -0.0996   -4.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.5503   -4.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -1.6959   -3.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -0.3977   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 26 27  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 30 28  1  0
 26 28  1  0
 11  9  2  0
  7  8  2  0
  9  7  1  0
  9 10  1  0
  7  6  1  0
 28 29  1  0
  4  6  1  0
 22 23  1  6
  2  3  1  0
 17 18  1  0
 12 11  1  0
 12 13  1  0
  4  3  1  0
 13 14  1  0
 22 17  1  0
 14 15  1  0
 17 12  1  0
 18 19  1  0
 22 27  1  0
 19 20  1  0
  4 11  1  0
 14 16  2  0
 32  2  1  0
 19 21  2  0
 31 30  1  0
  4  5  1  6
  2  1  2  3
 32 33  2  0
 31 64  1  0
 31 65  1  0
 30 62  1  0
 30 63  1  0
  3 36  1  0
  3 37  1  0
  1 34  1  0
  1 35  1  0
 17 46  1  1
 12 42  1  6
 26 57  1  6
 25 55  1  0
 25 56  1  0
 24 53  1  0
 24 54  1  0
 28 58  1  1
 10 39  1  0
 10 40  1  0
 10 41  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
  5 38  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       1.054  -3.981  -0.941  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.782  -2.671  -1.052  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.489  -1.588  -0.279  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.603  -0.864   0.773  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.719  -0.642   0.328  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.572  -1.638   1.965  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.169  -0.941   2.965  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.394  -1.371   4.082  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.516   0.405   2.492  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.092   1.401   3.423  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.149   0.457   1.207  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.225   1.583   0.203  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.327   2.467   0.513  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.560   2.044   0.123  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.590   3.067   0.487  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.802   0.983  -0.435  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.094   2.414   0.090  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.056   3.563   0.974  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.605   3.408   2.207  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.471   4.680   2.986  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.128   2.391   2.635  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.349   2.921  -1.367  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.769   3.834  -1.881  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.706   3.627  -1.491  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.639   2.497  -1.851  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.767   1.645  -2.763  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.430   1.769  -2.246  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.210   0.168  -2.860  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.640   0.077  -3.411  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.272  -0.689  -3.748  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.018  -1.221  -3.044  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.318  -2.280  -1.992  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.410  -2.840  -1.894  0.00  0.00           O+0
HETATM   34  H   UNK     0       0.499  -4.726  -1.507  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.824  -4.347  -0.270  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.365  -2.014   0.230  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.901  -0.887  -1.009  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.156  -1.515   0.351  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.497   1.460   4.340  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.114   1.119   3.696  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.123   2.406   2.997  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.421   1.143  -0.779  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.572   2.732   0.142  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.624   3.189   1.572  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.358   4.018  -0.001  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.947   1.776   0.345  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.587   4.924   3.117  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.923   4.550   3.974  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.992   5.489   2.469  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.898   4.716  -1.247  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.553   4.173  -2.901  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.722   3.302  -1.950  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.016   4.164  -0.590  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.699   4.352  -2.315  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.553   2.846  -2.339  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.923   1.944  -0.948  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.752   2.089  -3.768  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.218  -0.259  -1.851  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.706   0.517  -4.412  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.965  -0.967  -3.477  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.354   0.593  -2.762  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.964  -0.100  -4.621  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.825  -1.550  -4.143  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.627  -1.696  -3.794  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.543  -0.398  -2.603  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    3   32    1                                                  
CONECT    3    2    4   36   37                                             
CONECT    4    6    3   11    5                                             
CONECT    5    4   38                                                       
CONECT    6    7    4                                                       
CONECT    7    8    9    6                                                  
CONECT    8    7                                                            
CONECT    9   11    7   10                                                  
CONECT   10    9   39   40   41                                             
CONECT   11    9   12    4                                                  
CONECT   12   11   13   17   42                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   43   44   45                                             
CONECT   16   14                                                            
CONECT   17   18   22   12   46                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   47   48   49                                             
CONECT   21   19                                                            
CONECT   22   24   23   17   27                                             
CONECT   23   22   50   51   52                                             
CONECT   24   25   22   53   54                                             
CONECT   25   26   24   55   56                                             
CONECT   26   27   25   28   57                                             
CONECT   27   26   22                                                       
CONECT   28   30   26   29   58                                             
CONECT   29   28   59   60   61                                             
CONECT   30   28   31   62   63                                             
CONECT   31   32   30   64   65                                             
CONECT   32   31    2   33                                                  
CONECT   33   32                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    5                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   17                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   23                                                            
CONECT   51   23                                                            
CONECT   52   23                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   26                                                            
CONECT   58   28                                                            
CONECT   59   29                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   30                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   31                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  134    0
END

RDKit          3D

65 67  0  0  0  0  0  0  0  0999 V2000
    1.0535   -3.9807   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7824   -2.6710   -1.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -1.5878   -0.2791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6029   -0.8640    0.7730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7187   -0.6423    0.3279 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5722   -1.6383    1.9653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1692   -0.9410    2.9649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939   -1.3712    4.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.4054    2.4917 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0925    1.4010    3.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487    0.4568    1.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251    1.5827    0.2032 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3271    2.4673    0.5134 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    2.0442    0.1225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5905    3.0675    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8024    0.9833   -0.4346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    2.4139    0.0898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0563    3.5631    0.9743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    3.4082    2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4706    4.6801    2.9864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1278    2.3912    2.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    2.9207   -1.3670 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7685    3.8337   -1.8810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    3.6272   -1.4906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386    2.4968   -1.8506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7670    1.6453   -2.7634 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4295    1.7693   -2.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100    0.1683   -2.8595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6397    0.0766   -3.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -0.6887   -3.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0176   -1.2207   -3.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -2.2802   -1.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4099   -2.8395   -1.8936 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4986   -4.7258   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237   -4.3470   -0.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3646   -2.0145    0.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9010   -0.8865   -1.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1557   -1.5149    0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4966    1.4597    4.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1143    1.1188    3.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    2.4061    2.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    1.1432   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5725    2.7315    0.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6235    3.1892    1.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576    4.0175   -0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9470    1.7760    0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867    4.9241    3.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9229    4.5497    3.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    5.4890    2.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8982    4.7164   -1.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526    4.1727   -2.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    3.3021   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0162    4.1642   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6987    4.3519   -2.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    2.8461   -2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9229    1.9444   -0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7523    2.0889   -3.7676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182   -0.2587   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063    0.5165   -4.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9654   -0.9673   -3.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535    0.5931   -2.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9643   -0.0996   -4.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -1.5503   -4.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -1.6959   -3.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431   -0.3977   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 31  1  0
 26 27  1  0
 26 25  1  0
 25 24  1  0
 24 22  1  0
 30 28  1  0
 26 28  1  0
 11  9  2  0
  7  8  2  0
  9  7  1  0
  9 10  1  0
  7  6  1  0
 28 29  1  0
  4  6  1  0
 22 23  1  6
  2  3  1  0
 17 18  1  0
 12 11  1  0
 12 13  1  0
  4  3  1  0
 13 14  1  0
 22 17  1  0
 14 15  1  0
 17 12  1  0
 18 19  1  0
 22 27  1  0
 19 20  1  0
  4 11  1  0
 14 16  2  0
 32  2  1  0
 19 21  2  0
 31 30  1  0
  4  5  1  6
  2  1  2  3
 32 33  2  0
 31 64  1  0
 31 65  1  0
 30 62  1  0
 30 63  1  0
  3 36  1  0
  3 37  1  0
  1 34  1  0
  1 35  1  0
 17 46  1  1
 12 42  1  6
 26 57  1  6
 25 55  1  0
 25 56  1  0
 24 53  1  0
 24 54  1  0
 28 58  1  1
 10 39  1  0
 10 40  1  0
 10 41  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
  5 38  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(1S,2R,3S,8R,14S,15R)-3-(Acetyloxy)-8-hydroxy-1,5,14-trimethyl-10-methylidene-6,11-dioxo-7,18-dioxatricyclo[13.2.1.0,]octadec-4-en-2-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₂O₉

Average Mass

464.5110 Da

Monoisotopic Mass

464.20463 Da

IUPAC Name

(1S,2R,3S,8R,14S,15R)-3-(acetyloxy)-8-hydroxy-1,5,14-trimethyl-10-methylidene-6,11-dioxo-7,18-dioxatricyclo[13.2.1.0^{4,8}]octadec-4-en-2-yl acetate

Traditional Name

(1S,2R,3S,8R,14S,15R)-3-(acetyloxy)-8-hydroxy-1,5,14-trimethyl-10-methylidene-6,11-dioxo-7,18-dioxatricyclo[13.2.1.0^{4,8}]octadec-4-en-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12OC(=O)C(=C1[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])[C@]1(O[C@]([H])(C([H])([H])C1([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C(=O)C(=C([H])[H])C2([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H32O9/c1-12-7-8-17(27)13(2)11-24(29)19(14(3)22(28)33-24)20(30-15(4)25)21(31-16(5)26)23(6)10-9-18(12)32-23/h12,18,20-21,29H,2,7-11H2,1,3-6H3/t12-,18+,20-,21+,23-,24+/m0/s1

InChI Key

SRKPHIQXGQJUBL-UVVXZCJPSA-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
Pachyclavularia violacea	JEOL database	Sheu, J.-H., et al, Tetrahedron 57, 7639 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
2-furanone
Dihydrofuran
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.28	ALOGPS
logP	2.43	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.1	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.84 m³·mol⁻¹	ChemAxon
Polarizability	47.2 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

8565151

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10389709

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sheu, J.-H., et al. (2001). Sheu, J.-H., et al, Tetrahedron 57, 7639 (2001). Tetrahedron.

Showing NP-Card for Pachyclavulariolide K (NP0025395)

MOL for NP0025395 (Pachyclavulariolide K)

3D MOL for NP0025395 (Pachyclavulariolide K)

3D SDF for NP0025395 (Pachyclavulariolide K)

3D-SDF for NP0025395 (Pachyclavulariolide K)

PDB for NP0025395 (Pachyclavulariolide K)

3D PDB for NP0025395 (Pachyclavulariolide K)

SMILES for NP0025395 (Pachyclavulariolide K)

INCHI for NP0025395 (Pachyclavulariolide K)

Structure for NP0025395 (Pachyclavulariolide K)

3D Structure for NP0025395 (Pachyclavulariolide K)