NP-MRD: Showing NP-Card for 2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone (NP0266053)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 10:15:48 UTC

Updated at

2022-09-08 10:15:48 UTC

NP-MRD ID

NP0266053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone

Description

Physalin K belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). Physalin K is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, physalin K has been detected, but not quantified in, fruits. 2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone is found in Physalis minima. This could make physalin K a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312132D          

 40 48  0  0  0  0            999 V2000
    1.2369    0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -1.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1355   -1.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210   -1.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9407   -0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545   -1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4845    0.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816    0.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856   -0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888    1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4705   -0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0143    0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5734   -1.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    0.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131   -1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1268   -0.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7500   -1.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -0.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612    0.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244   -2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188    0.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939   -0.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -1.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -1.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6611    0.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    0.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491   -0.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722    1.7282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828   -1.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143   -0.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109    1.1936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7671   -3.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992   -2.3574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    1.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605   -0.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285   -2.2155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686    0.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1268   -0.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 18 14  1  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 22  1  1  0  0  0  0
 22  9  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 11  1  0  0  0  0
 23 18  1  0  0  0  0
 24  3  1  0  0  0  0
 24 16  1  0  0  0  0
 25  6  1  0  0  0  0
 25 21  1  0  0  0  0
 26  7  1  0  0  0  0
 26 15  1  0  0  0  0
 26 23  1  0  0  0  0
 27 12  1  0  0  0  0
 27 19  1  0  0  0  0
 28 17  1  0  0  0  0
 28 24  1  0  0  0  0
 28 25  1  0  0  0  0
 29 15  1  0  0  0  0
 30 18  2  0  0  0  0
 31 19  2  0  0  0  0
 32 20  2  0  0  0  0
 33 21  2  0  0  0  0
 34 25  1  0  0  0  0
 35 10  1  0  0  0  0
 35 27  1  0  0  0  0
 36 16  1  0  0  0  0
 36 20  1  0  0  0  0
 37 21  1  0  0  0  0
 37 24  1  0  0  0  0
 38 27  1  0  0  0  0
 38 28  1  0  0  0  0
 39 26  1  0  0  0  0
 14 40  1  0  0  0  0
 40 39  1  0  0  0  0
M  END

     RDKit          3D

 70 78  0  0  0  0  0  0  0  0999 V2000
    3.7748    2.1862    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7431    1.2353    1.4183 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0009    2.0225    2.2965 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4030    2.9686    1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0897    4.1751    1.6988 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1513    2.3041    0.1404 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8650    2.9829   -0.8194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2278    2.0661   -0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6074    2.1069   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0370    0.5994   -0.2418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0808   -0.3061   -0.9195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7983   -1.6170   -1.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8512   -2.0097   -0.2687 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6404   -3.0005   -0.8901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7604   -0.9564    0.2195 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4187   -0.7475    1.6785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1591    0.2009    2.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1572    0.7823    1.2724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8313   -0.3155    0.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1004   -1.1955    0.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3372    1.3447    0.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4113    2.4924   -0.1167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4539    0.3727   -0.5101 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8523    0.3141   -1.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382   -0.6616   -0.3208 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3222   -2.0244   -0.0340 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4698   -2.6419   -0.4468 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6564   -2.0918    0.2565 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3695   -2.0275    1.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8174   -2.9985    2.2913 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6932   -0.9212    2.4888 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5120    0.1163    1.9935 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2968   -0.4259    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2916   -0.8732   -0.2792 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1509   -1.2910   -1.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3992    0.2306   -0.7650 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2480   -0.4522   -1.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1452   -0.7651   -2.6098 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875    0.8933    0.3492 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7737   -0.0209    0.7162 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293    2.1059    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4483    3.2479    0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0230    1.9347   -0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081    3.1171   -1.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339    1.4535    0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0191    1.5698   -1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2049    2.5793    0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108    2.5552   -1.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8822    0.3921    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744    0.1287   -1.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0534   -2.4719   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2435   -1.6552   -2.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -2.5756    0.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939   -2.8517   -1.8662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631   -1.3009    2.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0763    0.5237    3.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8454    1.4724    1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3923   -0.6202   -2.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0201    0.5564   -2.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6139    1.1201   -2.1906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3588   -3.7209   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6151   -2.7356   -1.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4472   -2.9054    0.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2374    0.4915    2.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0282    0.2856    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8101   -1.3242    1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9223   -0.5502   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5305   -2.3071   -1.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4110   -1.3851   -2.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9265    0.8196   -1.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 20  1  1
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 18 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  6
 11 25  1  0
 25 40  1  0
 39 40  1  1
 39 36  1  0
 36 37  1  0
 37 38  2  0
 36 34  1  0
 34 35  1  6
 34 33  1  0
 33 32  1  0
 32 31  1  0
 31 29  1  0
 29 30  2  0
 29 28  1  0
 28 27  1  0
 27 26  1  0
 39  2  1  0
 28 34  1  0
 32  2  1  0
 39  6  1  0
 23 10  1  0
 37 25  1  0
 16 15  1  0
 25 26  1  1
 23 15  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  7 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  6
 12 51  1  0
 12 52  1  0
 13 53  1  1
 14 54  1  0
 18 57  1  1
 17 56  1  0
 16 55  1  0
 24 58  1  0
 24 59  1  0
 24 60  1  0
 36 70  1  6
 35 67  1  0
 35 68  1  0
 35 69  1  0
 33 65  1  0
 33 66  1  0
 32 64  1  1
 28 63  1  1
 27 61  1  0
 27 62  1  0
M  END


  Mrv0541 05061312132D          

 40 48  0  0  0  0            999 V2000
    1.2369    0.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9811   -1.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1355   -1.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210   -1.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9407   -0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545   -1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4845    0.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816    0.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1856   -0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888    1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4705   -0.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0143    0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5734   -1.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050    0.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131   -1.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1268   -0.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7500   -1.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -0.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5612    0.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244   -2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5188    0.0695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939   -0.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5183   -1.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -1.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6611    0.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933    0.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491   -0.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5722    1.7282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828   -1.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6143   -0.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1109    1.1936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7671   -3.0857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992   -2.3574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8318    1.1831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605   -0.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285   -2.2155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4686    0.0766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230    0.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1268   -0.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
 18 14  1  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 22  1  1  0  0  0  0
 22  9  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23  2  1  0  0  0  0
 23 11  1  0  0  0  0
 23 18  1  0  0  0  0
 24  3  1  0  0  0  0
 24 16  1  0  0  0  0
 25  6  1  0  0  0  0
 25 21  1  0  0  0  0
 26  7  1  0  0  0  0
 26 15  1  0  0  0  0
 26 23  1  0  0  0  0
 27 12  1  0  0  0  0
 27 19  1  0  0  0  0
 28 17  1  0  0  0  0
 28 24  1  0  0  0  0
 28 25  1  0  0  0  0
 29 15  1  0  0  0  0
 30 18  2  0  0  0  0
 31 19  2  0  0  0  0
 32 20  2  0  0  0  0
 33 21  2  0  0  0  0
 34 25  1  0  0  0  0
 35 10  1  0  0  0  0
 35 27  1  0  0  0  0
 36 16  1  0  0  0  0
 36 20  1  0  0  0  0
 37 21  1  0  0  0  0
 37 24  1  0  0  0  0
 38 27  1  0  0  0  0
 38 28  1  0  0  0  0
 39 26  1  0  0  0  0
 14 40  1  0  0  0  0
 40 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12OC(=O)C3(O)CCC4C(CC(O)C56OOC(C=C5)C(=O)C46C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O12/c1-22-9-16-24(3)28-17(22)19(31)27(39-28,35-10-13(22)20(32)36-16)12-8-15(29)26-7-5-14(38-40-26)18(30)23(26,2)11(12)4-6-25(28,34)21(33)37-24/h5,7,11-17,29,34H,4,6,8-10H2,1-3H3

> <INCHI_KEY>
IRYOOASWRCIZCK-UHFFFAOYSA-N

> <FORMULA>
C28H30O12

> <MOLECULAR_WEIGHT>
558.5306

> <EXACT_MASS>
558.173726424

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
52.41040155936153

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone

> <ALOGPS_LOGP>
0.76

> <JCHEM_LOGP>
1.1831736236666668

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.527693065074224

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.67647116259769

> <JCHEM_PKA_STRONGEST_BASIC>
-3.332859999267251

> <JCHEM_POLAR_SURFACE_AREA>
164.11999999999998

> <JCHEM_REFRACTIVITY>
126.51989999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.309   1.062   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.431  -2.296   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.253  -3.524   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.199  -2.392   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.089  -0.623   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.955  -3.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.238   0.660   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.312   1.751   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.346  -0.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.846   2.453   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.478  -0.911   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.627   0.372   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.553   1.460   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.404  -2.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.849   1.847   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.584  -1.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.103  -0.706   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.867  -2.098   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.882  -0.665   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.048   1.083   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.659  -4.391   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.968   0.130   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.015  -0.815   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.967  -2.632   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.443  -3.042   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.701   0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.094   0.725   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.518  -1.823   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.535   3.226   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.181  -3.477   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.880  -1.800   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.074   2.228   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.299  -5.760   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.105  -4.400   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.419   2.208   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -1.606  -0.492   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.173  -4.136   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.741   0.143   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       9.936   1.558   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       9.570  -0.440   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    6   11                                                       
CONECT    5    7   14                                                       
CONECT    6    4   25                                                       
CONECT    7    5   26                                                       
CONECT    8   12   15                                                       
CONECT    9   16   22                                                       
CONECT   10   13   35                                                       
CONECT   11    4   12   23                                                  
CONECT   12    8   11   27                                                  
CONECT   13   10   20   22                                                  
CONECT   14    5   18   40                                                  
CONECT   15    8   26   29                                                  
CONECT   16    9   24   36                                                  
CONECT   17   19   22   28                                                  
CONECT   18   14   23   30                                                  
CONECT   19   17   27   31                                                  
CONECT   20   13   32   36                                                  
CONECT   21   25   33   37                                                  
CONECT   22    1    9   13   17                                             
CONECT   23    2   11   18   26                                             
CONECT   24    3   16   28   37                                             
CONECT   25    6   21   28   34                                             
CONECT   26    7   15   23   39                                             
CONECT   27   12   19   35   38                                             
CONECT   28   17   24   25   38                                             
CONECT   29   15                                                            
CONECT   30   18                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   25                                                            
CONECT   35   10   27                                                       
CONECT   36   16   20                                                       
CONECT   37   21   24                                                       
CONECT   38   27   28                                                       
CONECT   39   26   40                                                       
CONECT   40   14   39                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₀O₁₂

Average Mass

558.5306 Da

Monoisotopic Mass

558.17373 Da

IUPAC Name

2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone

Traditional Name

2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone

CAS Registry Number

Not Available

SMILES

CC12OC(=O)C3(O)CCC4C(CC(O)C56OOC(C=C5)C(=O)C46C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5

InChI Identifier

InChI=1S/C28H30O12/c1-22-9-16-24(3)28-17(22)19(31)27(39-28,35-10-13(22)20(32)36-16)12-8-15(29)26-7-5-14(38-40-26)18(30)23(26,2)11(12)4-6-25(28,34)21(33)37-24/h5,7,11-17,29,34H,4,6,8-10H2,1-3H3

InChI Key

IRYOOASWRCIZCK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Physalis minima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Physalins and derivatives

Direct Parent

Physalins and derivatives

Alternative Parents

Substituents

Physalin skeleton
Delta_valerolactone
Ketal
Oxepane
Cyclohexenone
Delta valerolactone
Gamma butyrolactone
Ortho-dioxane
3-furanone
Oxane
Dicarboxylic acid or derivatives
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Ketone
Dialkyl peroxide
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	0.76	ALOGPS
logP	1.18	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	164.12 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	126.52 m³·mol⁻¹	ChemAxon
Polarizability	52.41 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034347

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020716

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73816389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone (NP0266053)

MOL for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

3D MOL for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

3D SDF for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

3D-SDF for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

PDB for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

3D PDB for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

SMILES for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

INCHI for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

Structure for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)

3D Structure for NP0266053 (2,19-dihydroxy-13,16,23-trimethyl-6,10,17,26,27,30-hexaoxanonacyclo[23.2.2.1⁵,¹⁴.1⁵,¹⁵.0¹,²³.0⁴,²².0⁸,¹³.0¹¹,¹⁶.0¹⁵,¹⁹]hentriacont-28-ene-9,18,24,31-tetrone)